It was his company, his idea, the source of his energy for nearly a decade. But he no longer wanted to be there.

To be honest, he’d known for some time. Maybe more than a year ago.

But there was no succession plan. No one he felt safe enough to confess to. The business was not robust enough. The Board wouldn’t trust anyone else to lead. His fellow leaders would panic if he left.

So he stayed silent, while his apathy slowly seeped into his work.

Decisions that he could have made within hours were now taking days. Issues that had previously felt minor began to grow in scale and complexity. The rhythms and demands of the business started to feel like a ball and chain, dragging him down slowly and steadily each day.

His colleagues, the other leaders on the team, felt something was off, but they rationalized it: it’s just a passing down cycle. He’ll snap out of it.

They did what too many organizations and leaders do, but later wish they hadn’t: They waited.

Is this happening in your organization?

It happened in several of mine. I saw it happen to other leaders as I stood by the sidelines, trying to avoid the issue.

Eventually, it even happened to me. I was the leader who wanted to go, but didn’t know how. I let it drag on for months.

Just as my boss, the CEO, was rationalizing the decision to wait, I was doing the same. I wasn’t sure what I wanted to do next. I didn’t want to be without income — that felt irresponsible. There was always one more meeting, one more project, one more client conversation I couldn't walk away from.

And yet, if I’m really honest, the core of what I was unwilling to confront was shame, guilt, and fear. Shame that maybe I couldn’t cut it. Guilt that I would be leaving my team behind to fend for themselves. And fear of the unknown, and whether it was actually OK to leave.

It’s easy with 20-20 hindsight to be critical. But when you’re in it, it’s a completely different experience.

You either don’t even know it’s happening.

Or you’re so wrapped up trying to avoid the issue, you forget that you have a choice.

You always have a choice.

Losing a leader, especially one with a long tenure, doesn’t just feel scary, it’s downright horrifying.

The reasons aren’t far-fetched. They’re rather logical.

If you’re brave enough to even contemplate the issue, the litany of questions to deter you from taking action is never-ending and impossible to answer:

What will people on the team think?
How will we replace their years of knowledge?
How will customers respond? Will they get spooked?
Could we have done something different to retain them?
Will the rest of the leadership team stick around for who’s next?
What if we can’t find a better replacement?

The uncertainty is too anxiety-inducing to face.
So instead, we avoid it.

We make excuses — Now isn’t the right time. They just need more support.

We justify — They wouldn’t push us out. We need to give them a little longer.

We deny the truth — The risks aren’t that bad. We can’t create a feasible mitigation plan.

We let our fears drive our path forward and let our leadership judgment slip out the back door.

It’s a terrible path, but it often feels like the easier one to take.

What starts easy turns hard… fast.

A leader who no longer wants the job is one of the most dangerous people you can keep on a team.

Even if they don’t want to hurt the company. In fact, the ones who still want to help are the most lethal. The ones who still want to do right but have not yet acknowledged that they no longer want in.

Those are the ones that wreak the most havoc.

Why?

Because what they are doing is insidious, not conscious, and wrapped in the veneer of good intentions.

The ones who are openly difficult, negative, and malicious make it obvious that they are a threat. You might still take too long to remove them, but at least it’s all out in the open.

The ones who are still parroting the mission and goals (but are questioning the strategy), show up looking prepared (but are only going through the motions), take on just enough work (but nothing extra or more risky) — those are the ones to worry about.

They hurt your progress and your team through small, seemingly innocuous acts:

• Confusing the team through small misdirections — “Don’t follow what was said in that last email. They don’t know what they’re talking about.”

• Creating mini-fissures through gossip — “Did you hear what [so-and-so] said after the meeting? I don’t think they are on board, but don’t talk to them about it.”

• Blocking progress with small comments — “I’m not sure why we are bothering. It hasn’t worked in the past.”

They will subtly add doubt to a discussion. They will delay key decisions. They will think smaller. They will focus on risks more than opportunities. They will shift your overall ethos from growth and innovation to steadiness and risk mitigation.

Your team will feel the pain, but won’t necessarily understand where it’s coming from and why. They will just start to feel the organization stagnate or stumble more. Work will become more arduous and progress more elusive.

And the leader who is struggling? They won’t even know they are doing it.

Because they are in denial just as much as you are.

Facing reality: motivation is what unlocks skills and knowledge.

Obligation is not the same as motivation.

That’s what leaders who no longer feel connected to a business confuse. They think their loyalty and commitment can hide their lack of energy for the mission and the work.

But they aren’t interchangeable. And one can’t mask the other.

“Have-to” thinking may yield some short-term results, but it will not unlock someone’s full potential. It will simply burn them out.

Even if a leader is the smartest person in the room and knows where all the bodies are buried, they won’t be powerful or even productive if they are no longer feeling motivated.

I like to think of our skills and knowledge as sitting in a metal canister. They may be valuable, but no one can see them or access them until you open the canister.

The opening only happens when you feel motivation. It comes from within and can’t be manufactured.

Sometimes, you can adjust the conditions to make it easier to create the opening for someone:

• Finding something adjacent and connected that matters to them can be a motivator (e.g. money, or the ability to learn)

• Adjusting the role and responsibilities to make them fit their current lifestyle needs and interests (e.g. going remote, or scoping down or up)

• Adding support structures and systems can make the job easier to navigate (e.g. a chief of staff, a coach, or AI agents)

But sometimes, those adjustments aren’t enough. They just don't feel as connected to the work anymore.

No amount of external work will solve that. And if they can’t see it, it’s your job as a leader to address it.

Because the alternative is too costly. It isn’t just lost time, it’s losing the momentum, the focus, and ultimately, the trust of your team.

Your turn.

Have you ever worked alongside a leader who was ready to go, but didn’t know it? Or maybe you were the leader, and it took you a minute to realize it was time?

I’d love to hear what helped you and the organization transition through that time — and what didn’t. If you’re willing to share, please add a Comment. I’d love to hear from you.

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If this post resonated, or made you pause and consider your own motivation level or that of your fellow leaders, please consider giving it a ❤️ and sharing it with a friend or colleague who would also benefit. Thank you!

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Mark your calendar for my next Substack Live.

This Friday, I’m talking with Olympic Gold Medalist and now a CEO Performance Coach — . Join us as he shares his key learnings from the training room to the board room. (Event Link)

As always, thank you for joining me each week as I dive into what it takes to lead without limits.

Yesterday morning, my paternal grandmother passed away.

I called her Nai Nai.

She was 101, and after months of fearing what was beyond, she told my father the hour before she passed, she “was going home.”

As I thought about my post this week, it became obvious: I’d share the lessons I learned from my grandmother, both what to emulate and what to avoid.

Her life was nothing notable for most people, and yet, it has always felt extraordinary to me, filled with courageous moves and perseverance almost to a fault.

I’m sad, and I need time to grieve. But grief is a funny business. It shows up differently for everyone. For me, the best way to honor my grandmother and process my feelings is to translate what I learned from her into leadership lessons I value and will continue to carry forward.

But before I share the lessons, let me give you some more context about my grandmother’s life.

From idyllic to turbulent, growing up without guarantees.

My grandmother grew up in China. I think it was in Jiangsu province on the eastern coast. (I wish I had more details, but thank you in advance for not judging.)

Nai Nai grew up in a well-to-do family. They had servants, cooks, and people who took care of my grandmother’s and the family’s needs. My grandmother started life sheltered. But all around her, the world was shifting. It was a time of significant social and political change.

Imperial China was ending. Women were no longer binding their feet, and they were starting to work outside the home. The Nationalists, Communists, and the Japanese were all battling for control. One of the few memories she shared with me was hiding in bomb shelters, and a deep distrust of Japanese people, all fostered in her early life.

As a young adult, she worked for the Nationalist government, and when its leader, Chiang Kai-shek, fled China before the Communists took over, she left, too. Her older sister was a leader in her local Communist Party outpost, and convinced the rest of the family to stay.

So, in a path that would be mirrored in the future, Nai Nai left her family and all her possessions behind and fled to Taipei, Taiwan, uncertain of the future, but convinced she could no longer stay in the home of her ancestors.

When I think about her decision, I can’t imagine what she might have felt. To go against her family and make an independent choice had to be hard, if not impossible. Daughters didn’t do that. And to go to a foreign land, with little to no money, and not know if you will see your family ever again? I know people around the world still grapple with this. And I am so fortunate that I can’t imagine it.

Leaving the workplace to work at home.

In Taipei, my grandmother met my grandfather, my Ye Ye, who also worked in the Nationalist government. The married and had 3 boys; my father is the eldest.

In Chinese culture, at the time, boys were considered princes, never to lift a finger, always to be prized.

Caring for 3 boys and my grandfather would have been a lot. But that wasn’t the family Nai Nai was responsible for.

My grandfather, unlike my grandmother, didn’t come to Taipei alone. He brought his grandmother and was joined later by his elder and younger sister and their families. This meant my grandmother was responsible for caring for all of them — alone.

Nai Nai left the workforce to become a full-time caregiver for a household that grew to 8. She did the daily shopping, prepping, cooking, cleaning, washing, and mending.

The long days of physical toil were brutal. Her hands were washed raw, her body ached daily. Her feet became deformed from wearing dress shoes that warped them as she trekked to complete her chores. She became humpbacked over time, and her spine never recovered.

But none of the physical labor compared to the emotional stress of being treated like a servant by her husband’s family members. It may have been the 1950s, but they held on to cultural norms of the past. The daughter-in-law was there to serve their needs, and they would make sure she did so.

Elite schools and American dreams.

My father and my uncles, with a few challenges, excelled at school. They were the picture of what Chinese families valued. And when it came time to figure out what came after college and their required military service, each left, one by one, for America.

And they never returned, at least not to live.

My grandparents came for a stint to stay with my family during the 1980s. While their time in Texas with us was fine, they could not tolerate the cold when we moved to New Jersey. Coupled with feeling trapped in suburban streets (they missed the city) and a community in which they couldn’t communicate (they couldn’t speak or read much English), they packed up and returned to Taiwan.

We missed them. I was fortunate. I had spent almost every summer of my life with them until elementary school. These were such formative travels that Mandarin felt like my first language, not English, even though I was born in the U.S.

My memories of my grandparents were of doting, caring people who spoiled me and loved me dearly. As I got older, they, along with my Mandarin, faded from my day-to-day life. They became foreign, a hazy concept — people I knew, but not really.

The struggles and peace in the final seasons of life.

I went back a few more times, once in high school and then in adulthood, but my visits were few and far between. Life had gotten full and trips to Asia were costly and time-consuming. I valued my grandparents, but I struggled to make time for them.

In 2002, my Ye Ye passed away from cancer. Nai Nai entered a new season of life. She was alone for nearly two decades, with brief visits from my father and his brothers. She was happy, I think. She filled her time as she liked and had a home health aide in her later years to help with household chores and personal care needs. In her senior years, she was finally the one being cared for, no longer the caregiver.

In 2020, my father relocated from China to live with Nai Nai as the pandemic raged. He was an anchor for her through those years, even if they struggled at times, each with strong opinions often held tightly. My mother joined them in 2023 for 6 months of the year, adding not just additional support but an emotional buffer to the people dynamics in my grandmother’s tiny apartment.

And in 2024, my family along with my uncles’ gathered for our first ever family reunion on my father’s side to celebrate my grandmother’s 100th birthday.

It was my kids’ first time meeting their great-grandmother (or Zhu Nai Nai as they call her) in person. But she wasn’t new to them. For several years prior, we had been doing weekly Saturday morning Skype calls to say hello. My kids don’t speak Chinese (I failed on that front), and so it was more of a brief 15-min nodding of heads with some light, poor translation from me. But I’d like to think it ingrained a few values that mattered in my children: honoring seniors, staying connected, and building in routines with meaning, to name a few.

My grandmother glowed during that visit. She was celebrated, doted upon, and the center of attention. She felt loved. I think it was a highlight of her life, seeing the family she built around her.

In the past year, my grandmother’s health started to decline. Her cancer returned and spread. Her once clear memory became fuzzy. Her fears started to guide her behavior, raising her suspicions, eroding sleep, and increasing her demands of others. Many of the qualities that enabled her to survive trying times started to impede her ability to gracefully enter the final stages of life. Stubbornness and relentlessness didn’t allow her to accept that the end might be near.

I am grateful that once she started hospice care at home with pain relief, Nai Nai suffered less. I’m also in awe of my parents who have put aside years of their own comfort and retirement dreams to care for her. It may have been Chinese cultural duty, but it was their personal commitment and love that made them stay in spite of, at times, truly difficult conditions.

Nai Nai was still talking throughout the night, even in her last few nights. It’s as if her mind still had things to accomplish, tasks that needed attention. But as her body guided her to rest, I think she finally realized in her final hour with my father, she had accomplished so much and was leaving behind a tremendous legacy.

My Grandmother’s Lessons

When I think about my grandmother, I don’t simply feel love or reverence. I feel a deep connection to what I learned from my grandmother’s journey and her behaviors. They aren’t all DO’s. There are some DON’Ts, too — because we can learn just as much from what doesn’t work as what does.

1. Focus on what matters and keep moving forward

Self-pity isn’t productive; action is. My grandmother had to make many difficult decisions in her life. She prioritized survival, her family's well-being, and, finally, her own happiness, choosing what mattered most in each season of life. And once she made a decision, she didn’t look back. She focused on moving forward.

Leadership Lesson
Priorities shift over time. The leaders who succeed are the ones who recognize the change and adjust their focus. They don’t waste energy ruminating; instead, they preserve their ability to navigate what lies ahead.

What’s one priority you need to re-evaluate? Stop avoiding the task. Schedule time to make a decision and move forward.

2. You don’t have to be alone

Even when all of her kids were across the globe, her only one of her grandchildren could speak so-so Mandarin (me), and gradually all of her friends passed away, Nai Nai didn’t choose to be alone. She sought out and found a few remaining family members in China (a maternal uncle and a maternal cousin). She welcomed thoughtful neighbors and community groups who periodically checked in on her. They brought small treats and made small talk. She didn’t push them away. She chose to get the support she needed.

Leadership Lesson
Leadership can be lonely. The weight of responsibility, the difficult decisions, and the confidential nature of the work. But you don’t have to go it alone. Trusted colleagues are there to support, and you can always bring in outside help: a coach, a therapist, a mentor, or all three.

Do you feel alone? Make a commitment to connect with someone you trust. If you don’t have one, source one. But don’t wait. Make this a priority for next quarter.

3. Take care of yourself when you can

Nai Nai couldn’t prioritize all her health needs when she was in the throes of taking care of 8 people. She was in survival mode. But as she got older and the weight of caregiving disappeared after my Ye Ye passed, she put herself first. Your health should always come first, but as a working parent leader, I know that it’s easier said than done at times. So do what you can, when you can.

Leadership Lesson
It’s never too late to take care of yourself. And if you don’t, no one else can help you.

What is one thing you could do to improve your health (mental or physical)? Start there. A doctor’s appointment. A 15 min workout. A 5-min stretch session. Don’t make it hard. Make it small and doable.

4. Enjoy what you can, when you can

Nai Nai has always loved food. She was a great cook and had a bit of a sweet tooth. In those early years in Taiwan, she and Ye Ye had to forego so much. So later in life, she was quick to ask for sticky rice with red bean or a pastry. She chose to savor what gave her joy. I’m convinced it was one of the reasons she lived so long — she enjoyed living.

What do you love about your work? What can you do to inject more of it into your day? Delegation, rescoping, and hiring additional talent. Be creative and be committed to making room for what lights you up. Do the same for your top talent and you’ll create a workplace that no one wants to leave.

5. Know when to let go

Nai Nai did this well earlier in her life and less so later in life. When she left China, she didn’t know she’d never see her mother again and wouldn’t be able to reconnect with any family until 30+ years later. But she knew to let go so that she could build a new life. When she was in her final year, she struggled to let go. She was so scared of death and beyond that she wouldn’t sleep, which added to her discomfort and stress.

Leadership Lesson
You can’t move forward if you can’t move on. Give yourself and your team the ability to move forward — let it go.

What are you holding on to that you should let go? A business idea, a team member, a decision that didn’t work out. Create a ceremony, journal your reservations, or talk to your coach or therapist.

6. You’re stronger than you think

Nai Nai faced terrible hardships throughout her life. They were made more stark because she was surrounded by comfort in her early years. But she made it through all of it. She had tremendous self-confidence and a belief that she could overcome anything.

Leadership Lesson
There will come a time when you don’t feel you’re equipped to do what it takes. Perhaps you’re behind on goals, or you’ve made a series of decisions that didn’t pan out. It’s easy to draw negative conclusions and to get demotivated. Your team needs you to stay strong.

Do you have anything making you feel down? If you need a moment for a pity party — do it. But then get back to it. Remind yourself of all you’ve accomplished and how you’ve navigated challenges in the past. You can do it again.

7. Don’t avoid change, embrace it

When I realized I wouldn’t be able to visit Nai Nai with my kids for several years, I asked my parents to buy her a computer and teach her to use Skype. She was 86. She didn’t complain. She didn’t resist. She didn’t worry about what was going to happen. She just learned how to take a video call with her granddaughter and her great-grandchildren. She wasn’t tech-savvy, and she didn’t need to be. She focused on the purpose of the tech and opened her mind to the possibility it was worth trying.

Leadership Lesson
AI, robotics, virtual reality, and more — there will always be a new technology out there. If you stay focused on your customer and team needs and stop worrying about constant change, you’ll choose wisely, learn what you need to learn, and invest in what your organization needs.

What are you overthinking? Can you take a simpler approach? Break the problem down and move forward with it in small chunks. Don’t let your fear decide what you do. That’s how the worst decisions are made.

Your Turn

My Nai Nai wasn’t perfect. No leader is. But she modeled essential leadership qualities that I emulated as I grew and evolved as a leader. And she was a grounding force when I faced adversity.

“Nai Nai survived. Nai Nai made it happen. I can, too.”

Too often, we think of leaders as people with big titles who lead large organizations. But as I get older, I realize that we have model leaders all around us, in our personal lives and in our community as much as in our professional ones.

Who have you looked up to as a role model leader? What did they help you realize and learn? I’d love to hear more in the Comments.

And if this post resonated with you today, please consider giving it a ❤️ and sharing it with someone who matters to you to help more readers find it and benefit from my Nai Nai's wisdom. May she rest in peace.

Thank you for joining me this week.

May you lead without limits,

I’ve never met a team that didn’t have issues with conflict.

It could be a leader who talks over everyone in a conversation. Or a long-tenured, senior expert who inspires enough fear in everyone to manipulate every decision. Or it’s isolated to two people who interact like oil and water, and disrupt every meeting.

Perhaps this resonates? If you’re being honest, I’m guessing you can name a few issues on your team.

Conflict isn’t in itself bad. As a leader, you know that.

But you also know that some types of conflict on your team don’t feel like the kind that is like medicine and will lead to good outcomes.

Too often, leaders want to jump to the solution. But unless you know the root of the issue, you risk addressing the wrong problem.

My recommendation is to start with a diagnosis.

How a night out with friends can help you diagnose the source of your team’s conflict.

I find that an analogy can sometimes help you achieve a helpful emotional distance from a problem.

If you’re like most leaders struggling with conflict on your team, you will literally feel your blood pressure rise as you think about the different issues and how they are hurting your organization and your goals.

So bear with me as I take us through one such analogy that has helped me:

Most of us have grown up with a group of friends. High school, college, and those roaring twenties. For many, these groups aren’t just a source of emotional support; they’re a source of fun activities.

When I think back, one of the things I loved doing with my friends was going to a party — a dance party.

But the process of going to a party wasn’t always easy.

• We sometimes had trouble choosing a party

• Some friends didn’t want to go to the party we chose as a group

• When we got there, some might not know the dance moves

• Even if you know the moves, you aren’t dancing in sync

• And if you wanted to switch partners, good luck. It was often difficult and a risky move. You might end up not clicking with anyone else

The point of a night of dancing with friends is simply to let loose, enjoy the music, and each other’s company. Everything above is the opposite — tension-filled, angst-inducing, and fun-zapping.

And it all maps well to team conflict:

• Can’t choose a party —> Lack of shared vision and goals

• Don’t want to go to the same party —> Misalignment of personal and organizational goals

• Don’t know the moves —> Unskillful interpersonal engagement

• Are not in sync —> Lack of behavioral norms and expectations

• Switching partners is awkward — Individual differences get in the way

These are the 5 ways most teams sink their performance even before they get started. Even if it is only a subset of the group that is the cause, their negative interactions contaminate the entire group.

To help you diagnose what’s happening in your team, let’s go a little deeper into each one.

The 5 Sources of Team Conflict

I outline the five sources I’ve found most common through my leadership and coaching experience. In addition to signals, I share one path to help you move forward. Each person and situation is different, but these have proven to work over and over again.

1. Lack of Shared Vision & Goals

When the team doesn’t know where they’re headed and why, it’s hard to be in alignment day-to-day.

Signals

• Your team is struggling to know what to prioritize

• They fight over one area being more important than another

• When you ask one person to name company goals, they answer differently from another teammate

One Path Forward

Take the time to clarify where you’re headed and why. Use scenarios to help make them clear — for yourself and your team. Everything sounds great until you start to apply it to real-world scenarios.

Start with a document to organize your thoughts. Chances are, you already have your goals written down. Add scenarios and examples. Then, the key is to incorporate conversation into your process. When people have a chance to engage live, that’s when you’ll learn if the direction you’re setting will hold up.

2. Misalignment of Personal & Organizational Goals

Sometimes, your team knows what the organization’s goals are, but they don’t align with their individual goals. Maybe someone wants to work less, but the organization needs people who are willing to push harder. Or the person wants more growth, but the organization is in steady-state or even downsizing.

Signals

• They consistently push a particular approach, regardless of context, complexity or relative importance (e.g. faster, slower, bigger, etc)

• They seem disengaged in the work and/or irritable

• They are argumentative beyond productive dissent and criticism

One Path Forward

Document your observations. Check with others what they have observed without asking leading questions. If you see a pattern, approach HR and discuss a path forward.

More likely than not, it means having a conversation with the person 1:1. Don’t hide your concerns, and don’t assume why they are behaving the way they are. Be curious and ask. And offer them the opportunity to share that they may not be aligned with the organization.

Even someone who is senior, long-tenured, or historically well-aligned can shift. And that’s OK. What you need to do is help them communicate openly about the shift, if they have shifted, and to align on what to do next. And if something else is the root issue, having this conversation will help as well because it’ll get at the root of a set of behaviors that is disruptive to the team.

3. Unskillful Interpersonal Engagement

Sadly, most professionals don’t get training on how to collaborate productively. Even if someone is a seasoned, experienced leader, it does not mean they are skillful in interpersonal engagement. Perhaps they didn’t need to be in prior roles, or others compensated around them.

Signals

• They struggle to listen actively and instead, speak over others or take up all the air space

• They avoid difficult conversations, either deprioritizing them or delegating it to other people

• When they engage, others leave the conversation deeply frustrated not simply based on what they discussed, but moreso how they choose to approach the topic (e.g. heavy handed, unclear communication, accusatory tone, etc)

One Path Forward

Given the person direct, and clear feedback where you outline their observed behaviors and the negative impact. Consider getting them a leadership or communications coach or sending them to training that will directly address their specific challenges.

Whatever you do, don’t wait. The longer you let their behavior persist, the more you are indicating to them and those around them that their behavior is acceptable. That is a surefire way to lose top talent.

If you find that it isn’t just one person, but a group of individuals who are challenged (possibly in different ways), then group coaching, 1:1 coaching, and/or group training may be necessary. The reality is that each person needs to up level, but they also need to be aware of how they may be triggering each other. No one exists in a vacuum; don’t treat the issue as if it can be easily quarantined.

4. Lack of Behavioral Norms & Expectations

Sometimes, your people aren’t being unskillful; they keep bumping into each other because they don’t know how to get in sync. (Imagine a group of people doing a line dance, but in completely different directions — it’s a mess!)

Signals

• People are talking past each other because they are at different stages of a process (e.g. one person is brainstorming, while another trying to plan)

• There aren’t clear roles and responsibilities and so people stepping on each other’s toes

• Critiques are becoming personal, and cliques are forming; meetings are starting to feel like a middle school lunchroom

One Path Forward

Draft a Code of Conduct and outline the behaviors you expect from the team. Invite discussion and conversation around the draft, including soliciting edits and additions. You’re not operating a democracy, but getting input is a helpful way to make sure you aren’t missing anything or misstating an idea. It’s also a way to build buy-in from your team.

One concept to include is “disagreeing and committing.” This allows everyone to commit to decisions even if they expressed dissent, and it ensures cohesion when the team starts to execute. It’s helpful for day-to-day operations. It’s also essential to align on the Code of Conduct (because, let’s be honest, not everyone will agree to every point) and move forward.

5. Individual Differences Get in the Way

Even when you have common standards of behavior and the same “dance steps” shared across a team, each person will still have their own style: of thinking, of communicating, of processing, and of disagreeing.

Having differences across the team is usually a great thing. The only time you need to address it is if it starts to impede progress and create unproductive tension.

Signals

• Someone becomes immovable in demanding that collaboration proceed a certain way, and always in that way

• Two people have different communication styles and are not hearing each other when they speak, and struggle to find a way to reach the other person

• Team members are starting to gossip about another teammate and their different approach to a body of work, but they aren’t approaching that team member

One Path Forward

The key to this issue is to address it early and before it develops into a pattern or theme. You don’t want anyone to become a target of ridicule or avoided because their reputation precedes them. This is true of the most junior person on the team or the most senior.

Don’t wait to dive into this one. It might feel more risky because it requires delving into a particular person’s style, but that doesn’t make it less worth addressing. It makes it even more powerful. Because of your intervention, that person may have a far more productive career future because you helped them get the feedback they critically need.

Your Turn

If you’re like most leaders, unproductive interpersonal conflict is just one of many issues on you long list of to-do’s.

It truly might not be one of the most urgent and critical things to solve, but it’s probably also costing you and your team more than you realize — not just in lost productivity at work, but in sleepless nights or at least more irritated commutes and dinner times.

If you’re not sure where it stands, talk to your team. Or just pause to observe what’s happening in your team’s interactions. What might realize may surprise you. It might not be an issue that is simply caused by your team’s lack of skillfulness or style differences.

The source might even be you. This your invitation to assess the situation before a truly negative outcome emerges.

If this piece was helpful to you, I’d deeply appreciate your sharing it with another leader.

I write each week about the topics I knew made a differentce for my teams and the businesses I led, but felt challenged by as a leader. With my newfound 20-20 perspective, I want to help more leaders make better decisions and build stronger organizations.

When you’re a leader of leaders, it’s that much more important to invest in your people and how they interact. If you’ve found ways to diagnose (and address) the type of team conflict that derails, I’d love to hear it in the Comments. I read and respond to every one.

And if you have a minute to give the post a ❤️, you’ll help more people find it on Substack.

Thank you for joining me and 2,000 other leaders on the journey to lead without limits,

It’s time for your weekly virtual team meeting.
You’re 2 min late as usual, and rushing in from another conversation.

The agenda is set. It should be routine, and you’re hoping the team brings a bit more energy today.

They’ve been dragging. It’s been intense, but there is a lot more to get done. You need everyone to show up and show up strong.

As you open the meeting and dive into initiatives, everyone seems to be paying attention, but when you ask if there are questions or alternative ideas, no one adds anything. The few that speak up only add “everything looks good.”

You push back on one person’s ideas, and she hesitates as if wanting to respond, but then acquiesces. You don’t notice it, but a few people’s eyes dart down, and it looks like they are typing. You chalk it up to note-taking.

You think you’re having one meeting. But there are actually two in motion: the one you see and the one you don’t.

Right alongside your meeting.
Everyone in your team is in it, but you.

Why?

Because they don’t trust you.

What’s even worse?

You have no idea.

You’re not alone. Most leaders have no idea when they’ve eroded trust and removed the conditions for psychological safety.

And to be honest, some don’t care.
This post isn’t for them.

This post is for the leaders who do care.

The ones who want to create an environment where their team can be successful and enjoy the ride. The ones for whom it isn’t just about the results, it’s also about relationships.

The good news is that you can do something about it — if you know what to look for.

But let’s start with why psychological safety matters.

Lack of psychological safety will sink your team’s results.

The research is clear:

When people are scared, they are less able to process complex ideas, less creative, and less likely to be happy.

In short, they’re less likely to perform well and less likely to enjoy the work. All the things leaders try to avoid when creating a productive workplace.

In the example above, it means fewer ideas, less dissent and debate, and more side conversations and gossip, which further erodes trust and creates more cognitive and emotional load — load that no one can afford.

So what does psychological safety even mean?

Let’s start with what it isn’t.

It doesn’t come from constant praise. It doesn’t mean giving people a pass every time they make a mistake. It doesn’t result from avoiding critique and hard conversations.

As defined by Harvard professor Amy Edmondson, who coined the term:

“Psychological safety is a belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes, and that the team is safe for interpersonal risk-taking.”

Even if your organization has high standards and is not tolerant of underperformance, you can create an environment that has a healthy level of psychological safety. Because at its core, psychological safety is about how you relate to each other — not technical skills or performance outcomes.

The leaders who create the conditions for psychological safety well understand this. They hold their teams accountable for performance while also creating ample room for interpersonal risk-taking.

But not every leader chooses to invest in psychological safety.

Why highly successful leaders don’t prioritize psychological safety.

There are many reasons why psychological safety doesn’t show up in leaders’ top priorities. I can’t cover them all, but I will highlight of what I’ve found to be the most common.

1. Creating psychological safety is not a prerequisite for success.

The old adage that you learn far more from failure than from success is an apt description of why so many leaders are blind to psychological safety.

Many leaders rise because they were in the right place at the right time. I’m not saying they didn’t earn the raise or the promotion. But sometimes they don’t encounter the diversity of situations and build the skills necessary to be an extraordinary, well-rounded leader.

When you are making great progress, even if it requires significant effort, you may not be aware of all of the elements that contributed to the foundation for your success.

It’s the gift and the curse of fast or smooth success, despite the research I cited above.

2. Overemphasis on outcomes over output.

Many organizations and leaders put too much focus on results only. It’s true that if you don’t achieve your goals, all the processes and activities you put in place may feel less relevant.

This can mean skipping over the behaviors and relational norms that help your team achieve those results in the first place and sustain them.

3. Some leaders were “raised” in work environments where psychological safety wasn’t part of the culture.

So they perpetuate what they know best.

Whether it be walking on eggshells with a facade of “politeness and niceness” or a rough and tumble, “survival of the fittest” model or something else altogether that stifles connection and smoothers direct conversation, some leaders just don’t know what they don’t know.

Regardless of the reason, once you realize the psychological safety is something that could help your team improve how it works, know that you can develop your ability to gauge whether your team is lacking in psychological safety.

Here’s how:

The signs are obvious only after you start to see them.

Like so many things in life, once you start to see them, you won’t be able to stop.

1. You receive little critical feedback

2. Your team doesn’t offer dissenting views

3. You are always right if there is a debate between you and your team

4. Your employee survey results are negative, but you don’t know why.

5. You don’t meet 1:1 with your direct reports (your EA or Chief of Staff is always present)

6. You don’t create time 1:1 or in group meetings to receive feedback.

7. Your team only shares examples of when things go well

8. You don’t know much about what matters to your team outside of work

9. Your team doesn’t know much about you and what matters to you outside of work

10. You get subtle suggestions from your team or colleagues to be more positive or to give your team time.

11. You feel like you’re carrying all the load for the team

There may be other signals as well, but this list should give you a good start. If you are experiencing 2-3 of these, it’s time to dig deeper.

How do you know it’s actually an issue?

You won’t know for sure until your team tells you.

But you likely have a sense that something is wrong. Your team is more quiet than outspoken. They say “yes” much more than they say “no.” You sense that the team’s work could be better, and they could be more engaged, more energized.

The only way to find out is to hear it from your team. Here are some ways to find out:

1. Talk with your team either as a group or 1:1 — Share your concerns and ask if they are seeing an issue. This requires finesse and judgement on when and how you broach the subject. But don’t overthink it and don’t delay.

2. Talk with trusted colleagues — Your team doesn’t work in a silo. Ask cross-functional partners what they are hearing and experiencing. Sometimes, you just need a different perspective.

3. Be patient. Slow down and make space — Don’t wait to start the conversation, but also don’t expect all the answers to come pouring out. It took time create fear, and it will take time to eradicate it. The surest way to kill this process is to add more pressure to it.

4. Be vulnerable — Share more about your thoughts that might feel counterintuitive or surprising. Do it concisely so that you don’t suck up more air space. Model what it means to put yourself out there. If your team sees it, they are more likely to mirror it.

5. Hire an outside coach or consultant —Sometimes you need a third-party perspective and voice. Your team may not be ready to open up to you, but they may be willing to reveal what is happening to someone outside your team. Just make sure you are clear about ground rules from the get-go: what will be kept confidential, what will be shared, and how you all will move forward.

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Creating psychological safety is a marathon, not a sprint.

Similar to long-term health strategies, it takes time to see results from attempts to build psychological safety. People need time to build trust and new habits.

You’re helping your team shift their assumptions: from speaking up will result in a bad outcome to seeing that it will result in better performance individually and as a team.

These are not small shifts. They require practice, observing outcomes, and internalizing both. It could take weeks, it could take months.

The key is to keep dialogue open, continue to reiterate why it matters, and to recognize and reward the change in behaviors you want. The only way people will believe the shift is real is if they experience the benefits and witness evidence that demonstrates that what you say is true. And this needs to happen consistently and regularly.

Your turn.

I’d love to hear more about what has worked for you to create psychological safety in your team. How did you know something wasn’t working? What did you to change the dynamics? What felt obvious and what didn’t?

When you share your experiences, you help everyone in the Lead without Limits community grow. And you help more leaders create the kind of organizations we all want to work in.

Thank you for joining me this week. If this post resonated, the kindest thing you can do is share it with someone who needs it and give it a ❤️ so that more leaders can find it on Substack.

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And in case you enjoyed my Substack Live with Tom Hardin, I’m so excited to announce that his book Wired on Wall Street is now available for purchase. I got my copy last week.

May you lead without limits,

On the face of it, it was a dream team.

Senior, proven leaders with decades of experience.

They were transforming a company, shifting it into growth mode and making it transaction-ready.

They showed up to meetings on time. They came to a decision quickly. They were aligned on the next steps, and people shifted into action seamlessly.

And yet when it came to their collaboration, something seemed off. They contemplated few ideas. Very little was debated, especially highly strategic decisions. When there was dissent, it was about minor topics like the formatting of a deck or the timing of a meeting.

They were going through the motions of execution well, but their results were mediocre, and they weren’t improving.

When the leader came to me to help him and his team achieve higher performance, he had no idea what was brewing under the surface.

After the first few sessions, it was clear to me — this was a team that deeply feared conflict, with their leader and with each other.

What felt like safety was costing much more than each person realized. Without conflict, they were missing out on better ideas, smarter solutions.

Even worse, they were creating a culture that drained everyone’s energy walking on eggshells. Left unaddressed, the team would fall apart.

The good news? It wasn’t too late to fix.

Conflict isn’t a sign of risk. Misunderstanding it is.

Conflict gets a bad rap. It’s associated with wars and physical violence. It’s something culturally we teach people to fear and avoid.

And yet conflict can support problem solving, creativity, and innovation. Technological advancements, scientific discoveries, and creative endeavors often require productive friction to source diverse ideas, debate merits, experiment and test, and overcome setbacks.

So why does conflict trip us up?

Because not all types of conflict1 are productive, and most teams don’t take the time to identify which one needs addressing:

• Task conflict (disagreements about what to do or how to think about a problem) can lead to better decisions, more creative solutions, and higher quality outcomes — when managed well.

• Process conflict (disagreements about how work gets done, roles, resource allocation) is correlated with a decline in team respect and trust, as well as reduced team productivity and viability.

• Relationship conflict (interpersonal friction, feelings of dislike or disrespect) is almost always detrimental. It erodes trust, increases stress, and hurts performance.

The teams that navigate conflict well are the ones that understand the difference between each category and know how and when to address each.

The ones that struggle can’t distinguish between them and allow a task or process conflict to transform into a relationship conflict.

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Where to start and why.

• Build awareness and a common language around these different types of conflict. With a shared understanding and common language, it’s much easier to get alignment on why this matters and make the changes necessary.

• Take the time to discuss openly how conflict is impacting your team. Invite the team to share examples of where the team isn’t able to focus or execute well together because conflict is distracting or stalling progress.

• Commit as a team to improving how you navigate conflict. This needs to be a group commitment because conflict can arise at any time and with any configuration of people. Any efforts to effect change will be lessened if only a subset of the team is ready to engage.

• Learn how to identify the different types of conflict. Use specific examples and discuss them. Only when you get into particular examples will everyone develop the muscles to identify them as they emerge.

• Discuss how to navigate each type of conflict more effectively. This will be specific to each team, but will generally center around roles, responsibilities, goals, constraints, and acceptable norms. One of the most important elements is clarifying who the decision-maker is and how that gets determined for each situation.

• Make it safe to call out when you’re starting to drift from one type of conflict to another and to pause before continuing. The pause gives everyone engaged a chance to step back, away from the fray, calm their emotions and get some perspective. Are you slipping into relationship conflict when the real issue is process? Is someone getting caught up in a process element when another person is focused on task? Just the act of pausing can help everyone get back on track.

This might feel like a lot to work through to just get started, but when you are dealing with group dynamics and trying to correct unhealthy norms, you need to be thoughtful about how you set the foundation.

As you set up your guidelines, don’t worry about creating hard and fast rules. Just start with a few scenarios and create guidelines organically. The key is to get started and open up the conversation. Simply acknowledging that there is an opportunity to improve can help the team create more productive habits.

Your turn.

Most teams in my experience spend 90% or more of their time focused on the “what” of their work. Few take the time to step back and align on what I call “meta topics” on “how” they do their work, like conflict management. These conversations require thoughtfulness and a pausing of the work that feels uncomfortable.

But it’s exactly these types of topics that, when left unaddressed, can become a terrible distraction at best and a highly destructive force at worst.

I’d love to hear if you have spent time on your team talking about the “how”. And if conflict management is one of the topics you’ve addressed.

If you haven’t, may this post be your invitation to start the conversation. I’d love to hear what emerges.

If you found this post helpful, I’d greatly appreciate your sharing it with others who you think would find it useful.

And if there are other topics you’d like me to cover around team dynamics, please reply and let me know. I read every message, even if I can’t respond to them all.

May you lead without limits,

We started this Substack Live with technical difficulties, a fitting metaphor for our theme: disruption to reinvention.

Sometimes things break. Sometimes they break badly. And sometimes, how we respond defines everything that comes next.

My guest, , knows this intimately.

Fourteen years ago, Ron was a managing director at Barclays, building the Asian equity desk in the U.S., living the life he’d planned since college. He was an avid cyclist and triathlete, a husband, and father to three daughters. Then, on a seemingly ordinary Saturday after Thanksgiving, a driver fell asleep at the wheel and changed everything.

Ron woke up from a coma weeks later, paralyzed from the waist down, unable to speak, being told by his neurosurgeon that he would never walk again.

What struck me most when I first met Ron at our Wharton alumni networking group wasn’t his wheelchair. It was his warmth. Here was someone I’d expected to be one of the “sharks” from my Wall Street days, and instead I found someone profoundly human, funny, and present. Someone who had taken unimaginable disruption and somehow found a way forward.

This conversation isn’t about inspiration porn or making lemonade from lemons (Ron hates that phrase, by the way).

It’s about the messy, difficult, year-and-a-half-long process of accepting a new reality. It’s about finding purpose when your planned path disappears. And it’s about discovering that you’re far more powerful than you think—while also learning to accept what simply is.

For leaders navigating any form of disruption (career transitions, health challenges, market upheavals, or personal reinvention), Ron’s story offers something rare: honest wisdom about resilience that doesn’t minimize the pain.

The Weight of “Why Me?”

When Ron came home after five months in hospitals and rehab, his house looked the same. But his study had become his bedroom because he could never climb the stairs to his actual bedroom again. He threw himself into physical recovery with the same intensity he’d brought to Wall Street, but the results weren’t coming. He wasn’t getting back to what he was.

For a year and a half, Ron kept asking, “Why me? Why me? Why me?”

Then his wife, Betsy, who had been “incredibly patient,” finally said: “Enough. Shit happens to people and it happened to you, but you’ve got a family. You’ve got three daughters. They’re growing up. They need you to be a father. I need you to be a husband.”

That moment became Ron’s inflection point.

“All right, I’m just going to run with it,” he told himself. “This isn’t the life I planned. That’s not the life I ever pictured. But it is the life I have. And it’s not over. And there are still things for me to do.”

Notice what Ron says:

“I don’t know that I ever fully accept it, but I did own it.”

There’s profound wisdom in that distinction. Acceptance and ownership aren’t the same thing. You can own your reality, take full responsibility for what comes next, without accepting that it’s okay or fair or what you wanted.

Ownership is about agency.
Acceptance can sometimes feel like surrender.

Your Action:
If you’re in the middle of a disruption that feels unfair or overwhelming, give yourself permission to separate acceptance from ownership.

You don’t have to be okay with what happened.
You don’t have to like it.
But you can still own what you do next.

Ask yourself: What would ownership look like for me right now, even if I’m not ready to accept this?

When the Path You Planned Disappears

Ron had wanted a career on Wall Street since college. He lived it, breathed it, thrived in it.

He was the most senior person on the Asian equity desk at Lehman Brothers when it went under in 2008, already a massive disruption. He navigated that, landing at Barclays with even more responsibility, building out their U.S. sales team for Asian equities, including Japan.

Then the accident. And in 2012, long before work-from-home was standard, Ron realized: “I can’t do this.”

If there had been remote work options, he says, “everything would have been different.”

He could have managed the 2 a.m. calls to Asia. But the daily routine—getting into the office before 7 a.m., traveling to Boston every other week, the whole physical infrastructure of that life—was impossible now.

“Just like my whole routine, everything takes so much longer.”

The career he’d built for decades was gone.

But Ron didn’t stay stuck in that loss. Instead, he found himself exposed to a different problem: the home care system.

When he needed caregivers himself, he was shocked by the limited options. Either expensive agencies that gave you no choice in who showed up, or finding someone on your own, with no way to properly vet them.

“All these marketplace companies were forming, connecting buyers and providers online,” Ron remembered. “And we thought, well, why can’t we do something similar?”

That became Lean On We, a business that has now helped over 2,000 families in the greater New York area get better, more affordable care.

Ron couldn’t go back to Wall Street, but he found a way to have “a big impact on people in a more visceral way than I had previously.”

Your Action:
When your planned path disappears, look for the problems only you can see from your new vantage point.
Ron’s accident gave him lived experience with a broken system.

Your disruption—whatever it is—has likely exposed you to challenges, needs, or opportunities that others can’t see.

What problem are you now uniquely positioned to solve?

The Power of People Who Still See You

One detail from Ron’s story stuck with me: his network didn’t disappear when his mobility did.

In fact, they didn’t just support him, they helped him carve out a new path.

A former client who became president of a liberal arts school in Illinois invited Ron to be their commencement speaker.

Ron’s initial reaction? “I don’t know. I don’t know if I could do that. That’s a lot of work.”
But then he told himself: “If you don’t do it, you’re going to regret it.”

He went. His whole family came. Nearly 2,000 people heard him speak about living forward. “It was such an empowering experience,” he said.

A close childhood friend kept encouraging him to write and speak more:
“People want to hear from you. People are curious. People don’t know what life is like for somebody who’s paralyzed... You’re a manifestation that life isn’t over. And hearing from someone like you can make them think differently about their own challenges.”

These weren’t empty platitudes. These were people who still saw Ron—not as someone broken or diminished, but as someone with something valuable to offer.

They invited him to try something new. They pointed him in different directions. They believed in him when he was still figuring out how to believe in himself.

“I realized that I found writing meaningful,” Ron said, “sharing what I’m going through, partially for myself and partially because I could see that it had an impact on others as well.”

Now Ron is a keynote speaker, has built a growing newsletter, and is in the process of writing his first book. All because the people he impacted in his career and life needed him… in a new way.

Your Action:
Inventory your network not for what people can do for you, but for who still sees you clearly.

Who invites you to stretch?
Who points you toward new possibilities?
Who believes you have value to offer even when you’re not sure yourself?

Reach out to one of those people this week and tell them what their belief in you has meant.

Grit Without Delusion: The G.O.L.D. Standard

Ron has distilled his framework for resilience into something he calls “The New Gold Standard”—a nod both to his last name and his Wall Street career. It stands for:

• Grit

• Opportunity

• Learning

• Drive

The model came from what he’s learned since 2012 — since he took ownership of his new life. But what makes Ron’s approach different from typical resilience narratives is his refusal to traffic in false hope.

A couple of years ago, he tried an exoskeleton called ReWalk. Everyone was excited: “You’re going to be able to walk! You’re going to be able to do this and do that!”

But it hurt his shoulder, and more fundamentally, it wasn’t practical. Even in the best case, all it could do was let him walk in a park. “It wouldn’t have changed my life. I couldn’t get in this thing and get in the car and drive somewhere.”

It was like many of the other developments in spinal cord injury research that Ron has monitored. Yes, there have been exciting breakthroughs. But many of them help people with quadriplegia first—those without use of their hands and arms.

“Here I am watching with bated breath these developments, and then it’s a little bit like a mirage. I’m happy for these people who are going to be able to get this, but it’s not going to happen to me.”

There’s internal conflict in that: being genuinely happy for others while accepting that the help isn’t coming for you yet. “I’m disappointed, but I’m happy for people. And I’m just hoping that the next shoe will drop.”

This is the paradox Ron lives:
“I don’t think I have limiting beliefs. But I’m also realistic enough to know that some things aren’t possible.”

I’m consistently in awe of what Ron chooses to accomplish:

He’s run five marathons in a hand cycle.
He drives with hand controls—left thumb for gas, left hand for brake.
Getting into his car requires taking off one wheel, flipping the chair, taking off the other wheel, lifting the body over himself onto the passenger seat. “And that’s before I even leave the driveway.”

When I see Ron at our networking events, he always says, “I got it, I got it” even when I or others offer help. He does. But I also witness how much harder everything is.

Ron doesn’t deny the hard. He has simply figured out a way to live with it and through it.

Your Action:
Practice Ron’s paradox.

Challenge one limiting belief you hold about yourself or your situation:
What would you attempt if you truly believed you were “so much more powerful than you think”?

Simultaneously, identify one area where you’ve been holding onto false hope or unrealistic expectations:
What would change if you accepted that particular reality while still maintaining your agency everywhere else?

What Ron Would Tell His Younger Self

Near the end of our conversation, I asked Ron what he would tell his younger self. His answer surprised me:

“You are much more powerful than you think you are. The clichés that people have—some of them I think are terrible—but the idea that if you really put your mind to it, you can do a lot, you can do so much more than you think, that kind of cliché is true.”

Then he said something that I surprised me:

“I’m much more driven and much more purposeful now than I ever was. And I feel if I had been able to take this drive that I have now—that I so urgently need because I just need to work so much harder to get things done—if I had been able to bring that to bear earlier, I could have done different things.”

Read that again.

Ron is more driven now—in a wheelchair, navigating a world built for people who can walk—than he was as a high-performing managing director on Wall Street.

Why? Because necessity revealed capacity he didn’t know he had.

Most of us won’t access that level of drive until we’re forced to. But what if we didn’t wait? What if we took seriously the idea that we’re capable of far more than we currently believe?

Ron also clarified which clichés he hates. When people tell him he’s “taken sour lemons and made sweet lemonade,” he bristles:

“Really? Did I? I’m still in this wheelchair, by the way. That sour lemon still exists. I’m getting whatever juice I can out of it.”

Those platitudes, he says, “are meant to make people feel better, that this guy’s all right. You don’t have to worry about him. He’s got his act together.”

But he doesn’t need us to feel better. He needs us to understand that resilience isn’t about making everything okay. It’s about fortitude and perseverance in the face of things that remain decidedly not okay.

Your Action:
Don’t wait for a crisis to discover your full capacity.
Identify one area where you’ve been playing smaller than necessary—not because you lack ability, but because you haven’t urgently needed to show up bigger.

What would change if you brought Ron’s level of purposeful drive to that area starting now?

Moving Forward

Ron is working on a memoir. He’s focused on speaking, particularly to financial services audiences, the world he came from. He wants to share his perspective with young analysts and associates, with financial advisors who create wealth and independence for their clients but might not fully appreciate the importance of their work, and with leaders who want to create cultures where their people can reach their full potential.

“These are the sorts of messages that I can bestow on others,” he says.

He’s also continuing to build Lean On We, helping families navigate one of the most difficult transitions in life: caring for aging parents or managing their own care needs.

And he keeps showing up. At networking events. In the New York City Marathon (five times in a hand cycle). On Substack (Ron’s Ramblings) and LinkedIn. Doing the work.

When I watch Ron arrive at our gatherings, transferring from his car, navigating spaces designed for standing people, serving himself food while everyone else towers above him, I see someone living the truth he discovered:

• You’re more powerful than you think

• Your life isn’t over when your plan disappears

• Ownership matters more than acceptance

The world has a habit of telling people in wheelchairs that their lives are tragic, diminished, over. Ron’s existence is a quiet rebellion against that narrative.

Not because everything is fine—it’s not.

But because he decided that even in a life he never planned, never wanted, never asked for, there are still things for him to do.

And he’s doing them.

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Conversation Timestamps

[00:00 - 07:11] Introduction & The Accident

• Technical difficulties set the stage for our theme: disruption to reinvention

• Ron’s background: Managing Director at Barclays, building Asian equity desk

• The cycling accident: “She falls asleep, crosses the center line, and heads right at my buddy Zach and me”

• Waking up from a coma weeks later, paralyzed, unable to speak

• Ron’s reflection on showing his wheelchair on video calls

[07:11 - 16:27] The Lehman Brothers Collapse & Career Before the Accident

• Ron’s experience during Lehman’s collapse in 2008

• The cash advance story: trusting his instincts when talking points didn’t match reality

• His role selling Asian equities to U.S. institutions during Asia’s growth period

• What it meant to be on the equity desk covering China, Taiwan, Singapore, Hong Kong, Japan

• 50-mile cycling rides and physical fitness before the accident

[16:27 - 24:00] The Hospital, Rehab & Coming Home

• Two months in ICU, three months at Kessler Rehab

• The mental challenge of rehab: “No longer about healing you... it’s about teaching you how to live that life as a paraplegic”

• Coming home to a house that looked the same but wasn’t: the study became his bedroom

• The year and a half of asking “Why me?”

• Betsy’s intervention: “Enough. Shit happens to people and it happened to you, but you’ve got a family”

• Ron’s inflection point: “I don’t know that I ever fully accept it, but I did own it”

[24:00 - 30:00] The Birth of Lean On We

• Realizing he couldn’t return to his Wall Street career (pre-remote work era)

• Being exposed to the broken home care system as a patient

• The two inadequate options: expensive agencies with no choice, or DIY with no vetting

• Creating Lean On We as a marketplace connecting families with caregivers

• Helping over 2,000 families in the greater New York area

• The caregiver shortage crisis and immigration issues

• Empowering caregivers through direct relationships

[30:00 - 37:06] Global Perspective & Human Connection

• Ron’s memories of working with people in Hong Kong, Taiwan, Singapore

• The story of Jimmy Lai: from immigrant to billionaire to imprisoned activist

• “A guy who’s a billionaire could walk away and chose to be a symbol of everything that American values are supposed to be”

• Ron’s attempt to convince his family to move to Hong Kong

• The importance of building relationships across cultures

[37:06 - 44:56] Finding Purpose Through Writing & Speaking

• The TEDx talk opportunity

• Being invited to give a commencement speech at a liberal arts college in Illinois

• A childhood friend encouraging him to share his story more widely

• People’s misconceptions about life in a wheelchair

• The power of showing what’s possible: “If this guy in a wheelchair can do things, that is a mindset shift”

• Processing the word “inspiring”: “I’m just trying to live my life the best way I can”

• Ron’s relationship with technology and social media: bringing out the good in connectivity

[44:56 - 51:34] The New Gold Standard & What’s Next

• Ron’s framework: Grit, Opportunity, Learning, Drive

• Five New York City marathons in a hand cycle

• Working on a memoir and other books

• Focus on speaking to financial services audiences

• The importance of financial advisors’ work: “creating some sort of independence so people can go and live their dream”

• What Ron would tell his younger self: “You are much more powerful than you think you are”

• Being more driven now than ever before

• The clichés Ron hates: “You’ve taken your sour lemons and made sweet lemonade”

[51:34 - 57:50] Limiting Beliefs vs. Reality

• “I don’t think I have limiting beliefs. But I’m also realistic enough to know that some things aren’t possible”

• The exoskeleton experiment that didn’t work out

• Watching spinal cord injury research with hope and disappointment

• The mirage of breakthroughs that help others first

• Accepting what is while hoping for what might be

• The pairing of power and acceptance

• How to connect with Ron: LinkedIn, Substack (Ron’s Ramblings), rongold.live, and Lean On We

If Ron’s story resonates with you, you can find him on LinkedIn, read his Substack “Ron’s Ramblings,” visit his website at rongold.live, or learn more about Lean On We. And if you know financial services organizations looking for a speaker who brings real perspective on resilience, reinvention, and what actually matters, Ron is your person.

Share this post with leader who needs to learn more about the G.O.L.D. standard.

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What disruption are you navigating right now?
And what would it mean to own it, even if you’re not ready to accept it?

I’d love to hear from you—just hit reply or share a comment.

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May you lead without limits,

Hi there! 👋 Welcome to Lead without Limits, where I share weekly, actionable mini-guides based on real human experience (not theories and platitudes) to level up your leadership and career and feel more fulfilled in the process.

Only about 50% of employees strongly agree that they know what is expected of them at work, according to Gallup1.

(sigh) Unfortunately, that’s not surprising.

Even in a board game, where there are clear rules and objectives, there are a variety of ways to win (or lose).

In business, how you execute can be even more varied because the rules aren’t standardized, teams aren’t uniform, and the playing field is ever-changing.

Leaders know this, and yet, few give their team enough (or any) direction on what good is, and then get disappointed (and surprised) when their team misses the mark.

Their excuses are plentiful:

• “I’m too busy. I don’t have time.”

• “My team should know what I want.”

• “My expectations should be obvious.”

And the resulting problems multiply even faster:

• Wasted time because work has to be repeated

• Frustration from the leader, and from their team

• Missed or poor outcomes that lead to missed goals

• Top talent departing when they don’t see any improvement

It doesn’t have to be this way.

You can help your team deliver and make the process less difficult for them by setting up clear and effective expectations. Here’s how:

How to Set Expectations Well

The steps aren’t complicated, but each one has a purpose, and if you cut corners, you won’t maximize the opportunity.

When we lead well, the short-term benefits are only part of the picture. The long-term value is where the real payoff lies: a higher-performing team, developing leaders who can compound their results, and creating greater trust that will result in career-lasting relationships.

1. Set Aside Time

You can’t do the work if you haven’t given yourself the time to tackle it. And if this feels like a difficult task, all the more reason to set aside more time not less. Ideally, you set aside time weekly and monthly to accomplish the rest of the steps.

Take Action: I recommend at least 30 min weekly to reflect and to plan for adjustments the following week. In the future, you can reduce to 15 min. Monthly, set aside another 30 min to review your notes and adjust for the next month.

2. Assess & Don’t Assume

The issue to address and the one that trips up leaders most often is making assumptions about their team that they haven’t verified. Instead of assuming, assess actual data, observe behaviors, and ask your team.

• If you think your team is following all the steps, review their approach.

• If you think your team is collaborating well, ask others.

• If you think your guidance is clear, ask them.

Hope is nice in theory, but terrible in practice.

Take Action: Identify the areas where you have most concern and where there is the highest impact to the business. Then choose one thing to verify each week. You might find that this habit becomes easier over time and you can do more than one, but start with just one. And if you need to slow it down to one a month because of the complexity or scale of impact, fantastic. Quantity isn’t the goal. Impact is.

3. Prioritize & Tailor

You can’t and shouldn’t define everything. Focus on what’s most important and where your team needs the most guidance (e.g. a team that’s great at the technical elements, but isn’t savvy on people dynamics needs more guidance there and vice versa for the opposite skillset).

Take Action: Once you have identified the highest impact areas and verified where you team needs more guidance, assess where your team is strong and where it isn’t. Share more detail, offer examples, create group working sessions for when they need more help. Do the opposite in areas where they are already in a good place. This way, you’ll help them understand where they need to shore up their work and model how to do so.

4. Separate the What from the How and the Why

There are 3 different parts to setting expectations:

1. What is required: the outcomes, the results.

2. How it needs to be accomplished

3. Why is it important

When you communicate your expectations, be sure to distinguish each. The Why and the What always matter — don’t skimp on those. The How doesn’t always matter, but if you have boundaries or certain organizational norms you need your team to follow, don’t be mysterious — tell them.

By being clear on all three, your team will have more understanding of your specific expectations, but also how to anticipate your thinking going forward. It’s as if you’re giving them the algorithm in your head on how you set expectations. This is how great teams move fast and seamlessly.

Take Action: Setting expectations isn’t a complicated formula. Write down your What, How and Why before you connect with your team. Not sure if you’re being clear enough, prompt AI to ask you questions to clarify what you share.

5. Use Scenarios

Scenarios is one of the most underutilized managerial tool. They can help you communicate more nuance, give you insight into how your team thinks, and be an excellent tool to align with your team. As a bonus, they will get your team more engaged by creating a dialogue vs a one-way conversation.

Take Action: For each of the priority areas where you’ve identified that your expectations setting could be improved, imagine 1-3 scenarios that can help illuminate the What, How and/or Why. Bring one to your team in a test-run and explain what you’re trying to do. If everyone walks away more clear, then you have a win. If people aren’t feeling more aligned, then try another one. Have patience with this one. It might take a few run.

6. Group Discussions Scale Learning

For all of the above steps, you can do them 1:1 or in a group. Take advantage of opportunities to do these steps as a group when you can. It not only reduces the number of conversations you’ll need to have, your team will benefit from observing how each other engages and how they are making sense of what you share.

Tailoring your approach to what people on your team need will determine which path you take and when. It’s OK to go slower when someone needs more individual attention or more relationship building to create trust. And when possible, leverage the power of the group.

Take Action: As you identify which expectations need your focus, think about when you can bring those conversations (verification moments, scenario discussions, etc) into a group meeting. Normalizing these won’t just help with expectations setting, it reinforce a open and collaborative mindset that will improve how your team works overall.

7. Verify Your Progress

Pause regularly to verify what’s needed, the quality of your guidance, and level of understanding. Unfortunately, there is no GPS telling you if you’re moving in the right direction. You have to do the work to find out if you’re heading in the right direction or if you need to course correct.

Take Action: Ask your team, ask their collaborators, check your team’s results, and reflect on your observations. These are all signals to help you make sense of your progress. This is technically part of step one and two, and so if you’re setting aside 30 min every week to do this, you’ll be far less likely to miss anything.

8. Periodically Revisit & Adjust

Treat expectations as an ongoing exercise vs. a set of edicts set in stone. There are too many changes happening too rapidly to assume what you’ve designed at the start of an initiative will still hold true several weeks later. It might, but it’s smarter to design your approach as if it won’t.

Take Action: Make sure your team knows that your expectations will be dynamic based on business context and what you all learn as you go. This way, they won’t be surprised when you make adjustments. It also invites them to come to you if they see changes that should inform any changes. This way, it’s not just about what you know, but it’s what your entire team is learning along the way.

The best part of getting this right?

You can rinse and repeat and the work you do once compounds. Your team more deeply understands not just what you want, but how and why. They will also be able to cascade your expectations to more people — direct reports, collaborators, and even external partners. This will give you leverage and create greater cohesion.

It can feel like a significant time investment because it is. But remember, like all smart investments, this up-front investment will generate significant returns. Over time, if you’re working with the same people, you will have less to align on because you’ve done the alignment work already and if you’re onboarding new people, your extended team can help you translate these into practice and you won’t have to be only standard bearer.

Don’t wait. Get started this week: Choose one important initiative and one team member to work with. And start to set aside the time to plant the seeds now for far better results going forward.

I’ll be cheering you on!

May you lead without limits,

P.S. SAVE THE DATE: My next Substack Live is scheduled for this Friday, January 23rd at 2:30pm ET with Ron Gold. You don’t want to miss this conversation on resilience and what it means to redefine success. Link to come soon!

If you found today’s post helpful, the greatest thank you can give me is sharing it with another leader who might benefit. Thank you!

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And if you would be open to sharing how you have set excellent expectations with your team, I’d love to learn more.

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This piece captures my recent Substack Live conversation with Tom Hardin, the former FBI informant known as Tipper X. You can watch the full video above, read the article below, or jump to the timestamp summary at the end to find the moments that matter most to you.

The $46,000 Decision That Changed Everything

What’s the price of a career built over years of hard work and education? For Tom Hardin, it was $46,000.

Not millions. Not even hundreds of thousands. Forty-six thousand dollars in personal gain from four small insider trades that added just 1% to his hedge fund’s performance.

When I first met Tom two years ago at a local networking event, and he introduced himself as “a former FBI informant,” I’ll be honest, I had no idea what that even meant.

What I’ve learned since has fundamentally changed how I think about ethical decision-making in leadership.

Tom’s story isn’t about a bad person doing bad things. It’s about a good person, Wharton-educated, hardworking, from a middle-class Atlanta family, who made four decisions in isolation that derailed his entire career at age 29. He then became the FBI’s top informant (codenamed Tipper X) in the largest insider trading investigation in history, spending two years wearing a wire to help take down corruption on Wall Street.

His upcoming book (Wired on Wall Street), launching February 25th, chronicles this journey. But our recent Substack Live conversation revealed something more important than the dramatic tale of espionage and courtroom drama: the anatomy of how ethical lines get crossed, and what leaders can do to prevent it.

Because here’s what struck me most: Tom’s experience is a cautionary tale for every leader navigating ambiguous situations under pressure. The kind of pressure we’re all facing right now: to grow faster, cut costs, hit quarterly numbers, stay ahead of AI disruption, do more with less.

Here’s what I learned.

Theme 1: The Slippery Slope Starts Long Before the Line is Crossed

Tom didn’t wake up one day and decide to commit securities fraud. The groundwork was laid years earlier.

Insider trading was “an open secret.” Everyone knew. Hedge funds would have value-added investors who worked at public companies call them with inside information. Or they’d hire analysts from tech companies specifically to call back for tips from their former colleagues.

Tom knew this was happening. And like many of us when we see problematic behavior around us, he told himself: “That’s happening, but it’s not my world. I don’t have those kinds of contacts. It wouldn’t be me.”

The critical mistake? He never asked himself: “If I were in that position one day, what would I do?”

There was no pre-mortem. No mental rehearsal. No conversation with a mentor about the ethical dilemmas he was witnessing. He simply put it out of his mind and went back to the intellectual work he loved—analyzing market trends, debating stock positions, building investment theses.

Then his boss came to him after a bad quarter and said: “We need to make money every month, Tom, or we aren’t going to survive. We have to start looking for shorter-term opportunities.”

Ambiguous. Pressurizing. Open to interpretation.

Tom didn’t ask clarifying questions. Are we talking about doing what everybody else is doing? Are we staying within legal and ethical guardrails?

Within months, a tip landed in his lap. Then another. And because he’d never mentally prepared for that moment, he rationalized: These other guys are going to make millions. I’ll just buy a small amount. Who am I hurting? It’s just one trade. I’m still a good person.

Action for Leaders:

Don’t wait for the ethical dilemma to arrive.
Create space now—in team meetings, in one-on-ones, in your own reflection time—to discuss the gray areas you’re witnessing in your industry. Ask yourself and your team: “If we were in that situation, what would we do?” Make the discussion discussable before the pressure is on.

Theme 2: Ambiguity Is the Enemy of Ethics

When I asked Tom what could have prevented those initial trades, his answer was immediate: clarity and conversation.

His boss’s directive—”we need to make money every month”—was the textbook definition of ambiguous leadership communication. And as Tom now tells companies around the world:

“Ambiguity is the enemy of ethics and integrity.”

Here’s how the dangerous pattern unfolds:

1. Leaders send ambiguous messages (”We have to hit this number” / “Do whatever it takes” / “I don’t want to know the details”)

2. Teams pretend the message wasn’t ambiguous (nobody asks clarifying questions for fear of looking difficult)

3. The ambiguity becomes undiscussable (”Are you questioning my communication? You know what I mean, just get it done”)

4. The undiscussability becomes undiscussable (culture of silence is established)

This is how you end up with values on the wall that don’t match the behavior in the halls.

Tom described visiting companies for compliance training where young employees pull him aside afterward and say:

“Yeah, what they say on the wall about speaking up? We would never do that here. If we raise our hand, we’ll never hear back and then we’re worried about our jobs.”

The fraud triangle that explains why employees cross ethical lines requires three elements:

1. Perceived need (pressure to perform)

2. Opportunity (lack of controls—in Tom’s case, he could buy stocks under 1% of assets without approval)

3. Rationalization (self-exception by reasoning—”I’m a good person, this is just once, it’s a small amount”)

But here’s what struck me: All three of these elements are amplified by ambiguous leadership communication.

Action for Leaders:

Audit your recent communications to your team. Where have you been ambiguous—perhaps intentionally—about how to achieve goals? Where might your team be interpreting “do whatever it takes” as permission to bend rules? Schedule a conversation specifically to clarify: What are we willing to do? What are we absolutely not willing to do? Make it safe to ask these questions.

Theme 3: Isolation Accelerates Poor Decisions

One of the most haunting moments in our conversation was when Tom said:

“If I had been talking to somebody outside my firm, outside my industry, maybe a mentor, and said, ‘Hey, you won’t believe what’s happening. These guys are making millions. I just got this tip. I’m thinking about taking a small trade just to play along...’ Certainly anybody on this call, if you’re my mentor, you would have slapped young Tom around.”

But he didn’t have that conversation.

He made the decision in isolation. And in isolation, it was very easy to do his own mental gymnastics: I’m a good guy. I’m a faithful husband. I go to church. I make thousands of trades a year. I can make four bad ones. They’re small. Who cares?

Tom told me:

“It would have been very hard to do that if I just jumped outside my head.”

This resonated deeply with me.

How many of us, when facing a difficult decision, keep it entirely in our own heads? We tell ourselves we’re being thoughtful, strategic, protecting confidentiality. But sometimes we’re just protecting ourselves from accountability.

After the FBI approached him, Tom could only tell his wife. For two years, he wore a wire, building cases against other traders, while maintaining his day job and his cover. He was juggling multiple, challenging identities: former trader, FBI informant, stay-at-home dad after he left his firm, ultramarathon runner.

But even after his name came out as Tipper X, even after sentencing, Tom said:

“I was so focused on myself. I hate to say it, I wasn’t really considering what my wife was going through.”

It wasn’t until he started volunteering at his church, getting outside his own head by helping others, that he began to heal. And it wasn’t until he was interviewed for his book that he finally asked his wife: “What was it like for you?”

Her response: “Thanks for asking, Tom, because you never did.”

Action for Leaders:

Build your “personal board of directors.” The 2-3 people outside your immediate team or company who you can call when you’re facing ambiguous decisions. Make it a practice to voice your dilemmas out loud, even (especially) when you think you have it figured out. The act of explaining your reasoning to someone else often reveals the flaws in your logic.

Note: Worried about confidentiality? Engage an attorney, have your confidants sign NDAs. Even when you get help, do it all above board.

Theme 4: Redemption Requires Radical Honesty and Service

When the FBI approached Tom on a Manhattan sidewalk at 6:30 AM on July 8, 2008, his first thought wasn’t about prison. It was: “Oh my gosh, my dad’s going to kill me.”

His father had worked for 40 years, commuting daily from their middle-class Atlanta suburb, so that Tom could have better opportunities. His mother had run a childcare business from their home. They had instilled in him a work ethic and drive to succeed that led him to read the entire World Book Encyclopedia when he was 8 (taking two years to get from “Akin to Zygote”) and eventually to Wharton.

And here he was, having thrown it all away.

His second thought:

“My wife’s going to leave. We just got married. She had no idea about the trades. She has every right to leave.”

But when he finally told her that Friday (after days of bed sweats and panic attacks), she said something remarkable: “You didn’t do anything to hurt me. And if they’re giving you a chance to clean up the industry, you should do it.”

Tom shared that 85% of marriages end in situations like this. His survived because of radical honesty and her extraordinary grace.

For two years, Tom worked as an FBI informant, meeting targets at Starbucks (he mentions it 15 times in his book, he laughed), trying to get them to admit to federal crimes. He was terrible at it initially—too eager to get to the punchline. The FBI would listen to recordings and say, “Tom, you’re doing a bad job. You have to be silent.”

There was no training at the FBI Academy for this. It was swim by being dumped in the deep end.

After his sentencing in 2015 (no prison time thanks to an FBI letter detailing his cooperation), he still had a felony conviction. He couldn’t get a job. His wife continued working while he became a stay-at-home dad.

He tried real estate deals (investors Googled him), drop-shipping on eBay (suppliers hijacked his listings). He volunteered at church, shipping clothes to Haiti. He ran ultra marathons to get fit and mentally heal, but it sometimes turned into a way to avoid difficult conversations with his wife about their financial reality.

Then he went on a podcast to tell his story. An FBI agent happened to be listening and called him: “Come talk to the FBI. What you discussed: the pressures, the dynamics, the rationalization. You could do a better job of compliance training for this industry.”

For a year, Tom emailed every business school in the New York area: “I’m Tipper X. I won’t charge for this. I’m just trying to get my reps.” A few schools let him in. Then a company asked: “How much do you charge?”

“$3,000?” he ventured.

He got paid. He told his wife: “You can quit your job.”

She replied: “Are you crazy? You just made $3,000. That’s it.”

But Tom said:

“When my family was at stake, when my wife had been so amazing, I knew I had to step up. I had to make this work. Whatever it was going to take.”

Ten years later, he speaks to Fortune 500 companies around the world. His first book launches February 25th. And his definition of success has completely transformed.

“It’s not about chasing status anymore,” he told me. “Success for me is more about special moments than outcomes. If somebody can pick up this book who knows nothing about finance or Wall Street, and maybe they’re going through a terrible, maybe self-inflicted situation in their own lives and can pull a few nuggets from this experience to help them—that’s what matters.”

Action for Leaders:

When things go wrong, whether through your own mistakes or your team’s, resist the instinct to minimize, rationalize, or hide. Radical honesty, even when it’s painful, is the only path to genuine redemption and rebuilt trust. And consider: How can you transform your hardest experiences into service to others?

One Question That Changes Everything

Near the end of our conversation, Tom shared something that crystallized all of these themes.

He’s read countless corporate codes of conduct, those documents we all sign (but very few actually read) annually with 10 philosophical questions to ask ourselves before making a decision.

At one European company, he asked if he could rip up their 10-question checklist on stage.

“Could you just ask yourself one question?” he proposed. “If I make this decision, am I willing to be held accountable for this decision at the end of the day?“

That’s it. Not five philosophical questions from your college ethics class. Just that one.

“If you can answer that,” Tom said, “you’re pretty much on the right path.”

Why This Matters Now

Tom’s story happened during the 2008 financial crisis, a time when the entire financial world was collapsing, when institutions that were never supposed to be wobbly were literally crumbling.

Sound familiar?

We’re living through our own period of unprecedented disruption. AI is transforming how we work. Economic uncertainty is putting pressure on every leader to deliver results. The temptation to take shortcuts, to be ambiguous about how we achieve goals, to look the other way when we see problematic behavior, to make decisions in isolation, has never been stronger.

Tom’s journey from rising hedge fund trader to FBI informant to keynote speaker and author isn’t just a dramatic story. It’s a mirror showing us what happens when good people face pressure without preparation, when ambiguity fills the space where clarity should be, when isolation replaces conversation.

The good news? Every single one of the risk factors Tom faced is preventable. Not easy to prevent, but possible.

It starts with having the conversations before the pressure arrives. With making ambiguity discussable. With building your board of directors. With asking yourself that one critical question.

Tom made four bad choices at 29. But he made one very good choice: he married his wife Sue. And through radical honesty, service to others, and a complete redefinition of success, he’s built a second career helping leaders avoid the mistakes he made.

His story reminds us that redemption is possible. But prevention is better.

Get the Book

Tom’s book launches February 25th. Companies ordering 10 or more copies will receive supplemental discussion materials around ethics decision-making.

Visit tipperx.com/book to pre-order (pre-orders in the next six weeks help move the algorithms during publication week).

You can also find Tom on Substack at tipperx.substack.com and on LinkedIn under Tipper X.

Conversation Timestamps

Want to dive deeper into specific parts of our conversation? Here’s your guide:

[00:00 - 04:04] Introduction and Tom’s background growing up in Atlanta

[04:05 - 08:05] The Wharton experience and dealing with imposter syndrome

[08:06 - 12:16] Landing the coveted hedge fund job and the tech bubble

[12:17 - 17:09] Becoming aware of insider trading as an “open secret”

[17:10 - 23:38] The moment of crossing the line: receiving the tip and placing the first trade

[23:39 - 28:02] The FBI approach on a Manhattan sidewalk

[28:03 - 33:03] Telling his wife and becoming an informant

[33:04 - 37:57] Two years wearing a wire and the Tipper X reveal

[37:58 - 45:00] The dark years: stay-at-home dad, ultra marathons, and finding purpose through service

[45:01 - 50:02] Sentencing, starting the speaking business, and writing the book

[50:03 - 55:10] What could have prevented it: lessons for leaders on ambiguity and organizational culture

[55:11 - 57:55] Closing thoughts on success, accountability, and the one question that changes everything

Thanks for reading Lead Without Limits. If you found value in this conversation, please share it with a leader who needs to hear Tom’s story. And if you’re facing an ambiguous situation right now, I’d love to hear about it. Sometimes we all need someone to help us jump outside our own heads.

May you lead without limits,

Hi there! Welcome to Lead without Limits, where I share weekly, actionable mini-guides based on real human experience (not theories and platitudes) to level up your leadership and career and feel more fulfilled in the process.

Whew! (*sigh*)

We’re on the other side of the end-of-year. A time that looks sparkly and festive on the outside, but actually drives most leaders bonkers with stress.

Budget negotiations, goal-setting machinations, end-of-year performance reviews, team celebrations, all while pushing to hit your annual targets — it’s no wonder leaders leave the season often feeling relief more than joy.

Perhaps one of the biggest drivers of stress is the feeling that you didn’t do enough, didn’t achieve enough, didn’t grow enough. This is often coupled with a stifling feeling masquerading as false optimism that this next year will be “better.”

You’ll hit higher targets, make more money, create more value — be more.

I don’t know about you, but that constant refrain of MORE starts off like an anthem but can, over time, devolve into the drumbeat of a death march.

What if this next year isn’t the year of more?

What if it’s the year of clarity, focus, and intentional subtraction?

What if it’s the year of less?

Every time I gave myself permission to choose “less”, I achieved more.

I confess, I love more. I grew up feeling in my bones that I needed more. More clothes, more friends, more travel, more food. It wasn’t that I didn’t have enough. I did. I just wanted more.

It wasn’t until I had achieved what was billed to me as the top of the job hierarchy after college (Tech investment banking on Sand Hill Road in 2001 — if you know, you know) that I realized that more on everyone else’s terms didn’t work for me.

More hours of work, more multi-million dollar deals, more late nights, more business trips — they not only didn’t match my interests, I tortured my body to force myself to do them. The more it felt bad, the harder I pushed.

Only when I left the finance world and started to work in client success for a small technology start-up, did I realize how choosing “less” could lead so much more.

It happened over and over in my career:

• Leaving a role at a 1000+ person, dysfunctional startup while 6-months pregnant to join a 10-person joint-venture because I was an after-thought in the first vs. an essential leader in the second.

  • Result: I helped launch a grow a $50M business and ultimately became CEO.

• Choosing to take a non-CEO role after my first stint as CEO because I wanted to work with people I trusted and needed health insurance to grow our family (infertility treatments are expensive).

  • Result: I made lifelong work friendships and my daughter was born 9 months later.

• Leaving corporate America in my mid-40s, at the supposed height of my executive career potential, to pursue my 20+ year dream of becoming a coach and artist.

  • Result: I get to spend my days doing everything I’ve longed to do with full autonomy and more creative energy than I’ve ever experienced in my life.

These decisions weren’t all roses and sunshine. But the end result was the same: By getting clear on what I was willing to deprioritize, I was able to make room for what actually mattered to me.

The most surprising outcome?

Once I made the decision on what mattered and what I was willing to let go, everything else flowed nearly seamlessly. What caught me even more off guard was that I was rewarded with far more than what I was seeking.

You can do it, too.
Here’s how.

Step 1: Look Further Ahead Than One Year

Start with visualizing where you want to be 1-2+ years from now.

Ask yourself:

• Who are you in this future moment?

• What matters to you?

• How do you feel?

Don’t overthink it. Trust your initial reactions. Jot it down. We’ll reflect on it in a moment.

Why that far out? Because real change takes real time. Even if you know this is a thought exercise, your brain is going to try to rationalize a response. Don’t. Use the distance to help you escape your current context and the short-term noise.

Step 2: Set Goals — and Anti-Goals

Using your vision as a guide, start to create a map of how you’ll get there.

Make 2 lists:

• Goals: What needs to happen to make your vision a reality

• Anti-Goals: What cannot to happen — this is what you’re intentionally deprioritizing

Don’t worry about timing or too many specifics just yet. This is meant to be a broad outline for now.

Both lists matter. The first tells you where you can focus your attention. The second helps you create freedom and space to maintain that focus without guilt and with more energy.

You know you’ve the exercise well when the first list makes you feel excitement (and maybe a few nerves, the worthy stuff usually does). And the second list should make you feel relief that you get to let some things go.

Step 3: Less Is Not Laziness — It’s Precision

This next step is a mindset shift.

You need it because you are rewiring deep programming. Even if part of you believes that less is more, more of you will still default to “more is more” as the answer.

Change requires repetition. Every day, schedule 5 min to remind yourself:

• Focus as a leadership advantage

• How fewer priorities create momentum

• Less rushing means more presence, more joy

Adjust the words to make them your own, put them on post-it’s, or use them as a meditation mantra. It doesn’t matter the specific method, it matters that you commit to reiterating it to yourself intentionally and regularly.

You’ll know you’re on the right track when you start to see the shift as not just something that will benefit you, but something that will benefit your team and the people around you.

Step 4: Prioritize 1-3 Goals (or Anti-Goals)

OK, it’s time to translate your vision goals and anti-goals into no more than 1-3 areas of focus for this next year. Ideally, choose just 1 to get started.

Use these questions to help you:

• What is something you can see yourself doing / stop doing this week?

• What will noticeably move you towards your vision?

• What feels more easeful, more frictionless?

Don’t worry too much about choosing the right one. Even just focusing on one thing will be progress. Sometimes the only way to know is to experiment.

Remember, less is more.
It’ll feel like it’s not enough. It’ll feel uncomfortable. You’ll hear an inner voice that will chastise you and make you doubt yourself. That’s a sign you’re on the right track. Hold steady. Don’t give in.

As you make progress, you can reassess what’s next. I prefer 3-month planning cycles. Too much changes too quickly to go far beyond that.

Importantly, don’t feel pressure to add more. If after 3 months, you’re feeling progress, and there is more to do (or not do), and you’re seeing the positive effects, it’s OK to stay the course.

The progress you can make with a singular, consistent focus can be life-changing. Don’t be afraid to give yourself (and your team) the opportunity to experience the full power of less is more.

You can do it!

“The ability to simplify means to eliminate the unnecessary so that the necessary may speak.”
— Hans Hofmann

The first time I did this exercise, I was so consumed by fear of not doing it correctly, the entire point of the exercise was lost on me. But then I tried again, and it landed.

The point isn’t to gain perfect clarity. The point is to give yourself permission to prioritize what matters and let go of the rest.

If this resonated with you, but you’re not sure if you can give yourself the time to go through the full exercise, don’t make this harder than it has to be.

• Just choose one thing that feels obvious and truly matters.

• Or choose one thing that you know isn’t adding enough value or is drain on your energy.

Let one of these these become your goal or anti-goal.

You can do this. You need to do this.
A focused leader is a more strategic leader.

Do it for your future self. Do it for your team. Do it for the people you serve.

I’ll be cheering you on!

May you lead without limits,

P.S. SAVE THE DATE: My next Substack Live is scheduled for next Monday, January 12th at 3:30pm ET with , otherwise known as TipperX — the most prolific FBI informant in Wall Street history. You don’t want to miss this conversation on Spies, Lies, & Tragedy: How One Leader Survived & Thrived. Download the Substack app to join. (Event link)

Hi there! Welcome to Lead without Limits where I share weekly, actionable mini-guides based on real human experience (not theories and platitudes) to level up your leadership and career and feel more fulfilled in the process.

From tears and frustration to power and optimism.
From fear and trepidation to confidence and clarity.
From false urgency and exhaustion to rest and rejuvenation.

2025 was a year of observation for me.
I bore witness to so many leaders stepping up and stepping in.

These were not easy moments.
In many cases, these were some of the most difficult seasons to navigate in their careers, but they chose to face them with courage and resolve.

Here are the themes that I found myself gravitating towards as I close out this year and prepare for the next. I hope they inspire you as much as they inspired me:

Theme 1: After a Layoff, Speed Isn’t Strategy

After years of climbing up, pacing ahead of others, and reaching pinnacles not out of breath, but ready for more, a layoff doesn’t just feel like a setback. It can feel like a deathblow.

For highly successful leaders, the first time is often the hardest. Coupled with the current business context of tightening belts, AI euphoria/mayhem, and geopolitical unpredictability, it can feel like the cards are stacked high against you.

Money may feel like a legitimate reason to hurry, but your psychological state is far more important. Rush into a search when you aren’t in the right frame of mind, and you’ll just be treading water, or worse, making a negative impression.

I saw over and over again, the leaders who paused, gave themselves time to process and heal, were the ones who pulled out of the negativity spiral. Networking, interviews, and decisions came easier when they weren’t consumed by anger, regret, and shame.

One found a larger role where they aren’t just essential (they always have been), but they feel valued and valuable in a way that wasn’t present in their last organization.

Another found a role that was more senior, higher pay, and with greater influence at a fast-growing firm with high-profile clients.

Another found a consulting opportunity in a domain they never would have considered in the past, but has now found deep fulfillment.

Go deeper: For more, read my post on how to reclaim your power after a layoff. Share it with a friend who might need a reminder to take care.

Theme 2: Isolation Feels Productive — Until It Isn’t

Leadership roles are, by definition, isolating.

Between the confidential information, the difficult decisions, and the volume of responsibility, it isn’t easy to share what you’re going through. It’s no surprise that most leaders have a tiny circle of confidantes, and even those are often partitioned by content areas, leaving few people, if any, having a full picture of what you are experiencing and navigating.

But this way of working takes its toll over time. Whether you choose to hire people to provide the support you need (therapists, coaches, etc), or you build a “trusted circle,” of friends, even leaders need outlets.

This is particularly true if you are feeling stressed or even lost. Being vulnerable feels risky because it is. But retreating into yourself often won’t help you find your way through darker or more challenging times.

As I close out 2025, my clients who have built these circles are the ones that remind me to continue to do the same. My most difficult moments in my career weren’t just characterized by work issues, they were also the moments when I was most disconnected from friends and family.

Go deeper: If you’re finding that you are feeling alone, consider one relationship you could build or strengthen. Make a commitment to do so in the new year.

Theme 3: Even Leaders Need to Be Seen

Too many people buy into the myth that senior leaders are self-sustaining, all-knowing, and omnipresent. They don’t need external feedback or praise. They should just “know.”

Even as someone who has been CEO and COO, I fall into this trap of assuming that leaders are somehow superhuman and therefore don’t require (or deserve) human considerations.

But it’s just not true: Leaders need recognition, too.

Feeling this way is not a sign that you are a narcissist or weak. It’s also not a sign that your team doesn’t care or doesn’t want to share.

It’s a sign you need to design systems to help you get the feedback and acknowledgement you need.

Go deeper: Learn how to source the validation you need in this LinkedIn carousel post. Implement one of these systems, and you’ll not only get more feedback, but so will your team.

Theme 4: Relationships First, Transactions Second

When you are in a high-stakes conversation, it’s easy to get focused on the transactional outcome: should we hire the candidate, can I save a few thousand dollars on the contract, etc.

But that’s a mistake.

The deal or decision may matter in the moment, but the relationship you are building (or destroying) will matter far longer. Share what you are thinking, give the other person the benefit of the doubt, and work together to find the optimal outcome.

When you reframe the situation as an opportunity to collaborate vs. an adversarial encounter, the process doesn’t just lead to better outcomes, it means that you’ll be building trust at the same time. The transaction may not matter 5 years from now, but the relationship will.

Go deeper: For more on how to prioritize collaboration even in a negotiation, read this post about a leader who negotiated a complex compensation agreement and got exactly what she wanted by providing the context her hiring manager needed to make a case for her.

Theme 5: Changing Habits Isn’t Linear — and That’s Not Failure

“Growth is uncomfortable because you’ve never been here before.”
— Kristin Lohr

Successful leaders are used to high expectations achieved at a high pace. But when you are changing deeper wiring, progress takes longer, is harder to predict, and success isn’t a hockey stick to the right.

My first corporate client this year had that exact experience. A C-suite leader and his team signed up for the Positive Intelligence mindset program I offer alongside one-on-one coaching.

Even as some of the group made strides quickly initially, others struggled to get started. They are part of a fast-changing organization with big ambitious goals. It is easy to lose momentum when your days are filled with curveballs and one high stakes decision after another.

My guidance? When you are changing a habit, don’t expect to change your immediate reaction or instinct — they are wired deep. The win is simply becoming aware of your reaction and pausing to choose your next action.

Once you start to reframe success as progress, not perfection, new habits become easier to adopt. Stumbles no longer feel like setbacks. They become part of the muscle-building you need to hone your new skills.

Go deeper: Interested in strengthening your mindset. Start with taking the Positive Intelligence Saboteur Assessment. It’s free and only takes a few minutes and what it reveals might help you determine what habit or skill you want to focus on next year. And you can always ping me if you want to explore how to quiet your saboteurs.

Your Leadership is Needed Now More than Ever

The world is in desperate need of more leaders, who are skilled and truly care about the people and organizations they lead.

The themes above highlight how challenging it is to be a leader today. But they also point to how leaders must first take care of themselves before they can provide the kind of direction, decision-making, and determination that can build successful teams.

As we close out the year, take the time to capture your themes:

• What are some of the challenges you faced?

• What is giving you energy and resolve?

• What helped you grow this year?

• How do you want to direct your attention going forward?

I’d love to hear more in the Comments below or in a reply to my email. I read every one.

I wish you the very best and look forward to seeing you in the new year!

May you lead without limits,

What started as a discussion about navigating AI and remote work became something much deeper: a masterclass in human-centered leadership during times of massive transformation.

Dan’s story isn’t your typical Silicon Valley narrative.

It’s one of immigrant resilience, calculated risk-taking, and the kind of thoughtful leadership that prioritizes people alongside profits.

In just 14 months, he helped transform Collectors from an $850 million acquisition into a $4.3 billion valuation; not through aggressive layoffs or flashy technology plays, but through sustainable growth and genuine investment in people.

Here’s what I learned from our conversation, and what you can apply to your own leadership journey.

Tip: Scroll to the bottom for a timestamped outline of our conversation so you can jump to the parts you care about most.

Everything Is Made Up. So Why Not Make It Better?

One of the most liberating things Dan shared was his perspective on change:

“Everything that you have that’s around you, that you do, that you’re living in, was made up by someone or a group of someones. There really is no reason why you couldn’t be and may not be one of those someones to build it for the next generation.”

This mindset comes directly from his parents’ story. As Vietnamese refugees who survived unimaginable hardship: cargo ships, refugee camps, and starting over in a completely foreign country with nothing. They taught him that no professional challenge could ever be as difficult as what they overcame.

But here’s the key: Dan doesn’t let this perspective make him reckless. Instead, it removes the paralyzing fear of the unknown while maintaining respect for the complexity of the work ahead.

Your Takeaway: When facing a daunting change or challenge, ask yourself: “What’s actually at risk here?” Often, our fears are disproportionate to the reality. This doesn’t mean being careless. It means being courageously strategic.

Real M&A Wisdom: Respect What Came Before

When Dan joined Collectors, he found a 35-year-old company with 750 employees and just 22 people in tech. The company was “collapsing under their own success:” outdated technology, manual processes, Post-it notes instead of digital systems.

The easy move would have been to sweep clean and start fresh.
He didn’t do that.

Instead, Dan spent time with each person on the team, understanding their strengths, their institutional knowledge, and their potential. He found people who had been with the company for 25-30 years, an almost unheard-of tenure in tech.

“You never hear about companies that have people stay for that long,” he told me. “That’s a wealth of information and stories and knowledge that you want to tap into if possible.”

His approach was to build career ladders, create clear departments, hire managers who understood enterprise-scale systems, and give people room to grow into specialists rather than remain overwhelmed generalists.

Surprisingly, he retained the majority of the original team through this transformation. Not because he had to, or from fear, but because it aligned with his values and was the smart thing to do.

Your Takeaway: Whether you’re joining a new company or leading a transformation, your first job is to understand what already works and why. The people who’ve been there have context you’ll never have. Your job is to create the structure and tools that give them the chance to thrive. The goal shouldn’t be to retain the team at all costs, but it’s a huge mistake to dismiss without first trying to build with them.

Make Trade-Offs Transparent (But Know Your Audience)

Here’s something Dan admitted publicly for the first time during our conversation: the board was questioning his abilities during that first year.

Revenue wasn’t improving fast enough. He was “exploding the budget” by hiring new people. The backlog was actually getting worse because he was adding process and onboarding people, which took existing team members away from their work.

They were seriously considering replacing him.

What saved him? Clear communication about trade-offs, calibrated to each audience.

For the board, Dan kept explanations high-level: here are the metrics improving, here are the signals to watch for, here’s why sustainable growth matters more than quick fixes.

When they asked about his strangler fig tree pattern for managing tech debt (gradually replacing old systems by building on top of them), he could see their eyes glazing over within 30 seconds. He adjusted: “Just trust me.”

For his team, the opposite was true. Dan practices radical transparency: “I tell them 100% of what I’m going to do, what the plan is.” He wants everyone, from engineers to marketing to HR, to understand the company’s revenue, the reasoning behind decisions, and the trade-offs being made.

This transparency meant his team understood why they were keeping ancient infrastructure in a closet (fire risk, night & weekend work, and more) while investing resources elsewhere. They knew why they couldn’t automate everything immediately. They understood the North Star and could make good decisions without constant oversight.

Your Takeaway: Different stakeholders need different levels of detail. Your board needs confidence in the direction and evidence of progress. Your team needs context to make good daily decisions. Neither is more important. They’re different jobs requiring different information.

The Real Cost of Moving Too Fast

While other companies were doubling and tripling their engineering teams in 2021-2022, (highlighted by Amazon raising their salary cap from $250K to $360K and everyone doing a land grab for talent), Dan grew his team by just 5-10 engineers.

The board questioned this too: “These companies are pulling in thousands, tens of thousands of engineers. You only increased by five or ten engineers. Why is that? Are you incompetent?”

His response?

“I would put a bet that they will all have to course correct how much they’re spending on engineers in the next couple of years... They’re paying high amounts now, but the ROI they’re getting from each engineer won’t match that.”

And yet behind his confident answers, Dan didn’t know for sure. He was trusting his instincts and his common sense. What other companies were doing didn’t make sense. His critical thinking paid off.

He was right. Those companies are now doing 10% layoffs, cutting salaries, and removing benefits. Meanwhile, Collectors continues to grow sustainably, adding salaries and benefits even in today’s economy.

Your Takeaway: Resist the pressure to follow what everyone else is doing just because “that’s what successful companies do.” Sustainable growth (in headcount, in technology adoption, in any transformation) almost always beats rapid scaling. The fast way is often the slow way in disguise.

AI Is a How, Not a What

When I asked Dan about implementing AI, his response was refreshingly pragmatic. He started building an AI department in 2021-2022 with one person whose job was simply to “tinker, experiment, and try a lot of different things.”

Four years later, they released an AI feature in their mobile app that can scan any trading card and identify it within seconds. But it took four years of experimentation to get there.

Meanwhile, his team experiments with 15-30 different AI startups and platforms at any given time. Everything from code generation to automated performance reviews to financial forecasting.

His philosophy?

“AI in general, to me, the way that you should think about it is it’s a how, not the what. It’s not the final goal.”

Some experiments work brilliantly. Dan now uses AI to draft performance reviews that sound exactly like him and are actually less biased than his own first drafts because they don’t suffer from recency bias.

Other experiments fail spectacularly. Ask an AI tool “how much revenue did we have last quarter?” twice, and get two different answers? That’s not ready for production.

The key is that Dan’s team is always experimenting, always learning, always asking: “What problems do we need solved?” first, then exploring whether AI can solve them better than manual processes.

Your takeaway: Don’t adopt AI because you feel you should. Identify the problems you need to solve. Problems that exist whether AI exists or not. Then explore whether AI solves them faster, better, or cheaper. And expect that half your experiments will fail. That’s not a bug; it’s the feature of experimentation.

Fighting for What You Believe In

Near the end of our conversation, I asked Dan what gets him “bent out of shape” at work. His answer was telling:

“The thing that really affects me the most at work is when we aren’t trying to push ourselves to be better.”

He shared an example from last year when the company was considering an expensive acquisition to enter a new business line. Dan believed they could build it themselves, better and faster. His product counterpart disagreed: they didn’t have the time, resources, or priority.

Dan made a bet:

“Give me a month. If you can hold off on that deal for a month, I think I can show enough progress to convince you otherwise.”

He got his month. He gave two engineers a project, a small budget, and a bounty for completion. Within three weeks, they had a working proof of concept. The acquisition was declined. The product they built became hugely successful, generating millions in revenue.

Your Takeaway: Sometimes leadership means putting your conviction on the line. Not recklessly, but strategically. When you deeply believe something is possible, and you’re willing to do the work to prove it, ask for the space to try. The worst case? You learn something valuable. The best case? You create something transformative.

The Why Behind It All

What struck me most about Dan wasn’t his technical acumen or his business results, impressive as they are. It was his clarity about why he does what he does.

He kept coming back to his parents, to the families who sponsored them, to the opportunities he was given.

“I just don’t want to waste it. I want to make sure that I’m making the most of it.”

But his why extends beyond gratitude. He has a vision of what’s possible when we help each other:

“Imagine a world where we’re all helping each other get the maximum... helping everyone to actually be the best version of themselves, how much more fulfilling life could be for each one of us, but also how much better the world could be for all of us.”

This isn’t just feel-good philosophy. It’s the foundation of every decision Dan makes: Will this help people be the best version of themselves? Will this make the world better?

When your why is that clear, the how becomes easier to figure out.

What This Means for Your Leadership

Here’s what I’m taking away from my conversation with Dan, and what I hope you’ll consider for your own leadership:

1. Reduce fear with perspective. What you’re facing likely isn’t as hard as your mind makes it. Ground yourself in what’s actually at risk.

2. Invest in the people who are already there. Transformation doesn’t require replacement. It requires structure, clarity, and space to grow.

3. Make trade-offs explicit and appropriate. Your board doesn’t need implementation details. Your team doesn’t need to be shielded from hard truths. Give each the right level of transparency so they can do their part.

4. Resist the pressure to move at everyone else’s pace. Sustainable growth beats rapid scaling nearly every time.

5. Experiment relentlessly with new tools and technologies. But always start with the problem you’re solving, not the shiny new solution.

6. Put your conviction on the line. Use your own judgment and critical thinking. When you believe something deeply, be courageous and ask for the space to prove it.

7. Know your why. It’s what will sustain you when the board is questioning you, when the transformation is messy, when the easy path looks tempting.

Dan’s journey from a kid coding games on a TI-82 calculator to a CTO who’s helped build a multi-billion dollar company isn’t just a success story. It’s a blueprint for human-centered leadership in an era of constant change.

The technology will keep evolving. The business models will keep shifting. But the fundamental work of leadership, helping people become the best version of themselves while driving toward a meaningful vision, that remains constant.

Want to connect with Dan? Find him on LinkedIn or visit his website at danvantran.com. And if you’re curious about the world of collectibles and how technology is supporting this thriving community, check out collectors.com to see the innovative work his team is doing.

What resonated most with you from this conversation? Hit reply and let me know. I read every response.

Conversation Topics & Timestamps

Jump to the topics that interest you most:

• 00:00 - 02:23 - Introduction and Dan’s background overview

• 02:23 - 04:24 - Why Dan is speaking more and navigating the “weird time” for tech leaders

• 04:27 - 08:50 - Dan’s family immigration story and his father’s journey into tech/telecommunications

• 08:50 - 12:50 - How Dan taught himself to code on a TI-82 calculator (and convinced his parents to let him keep it)

• 12:50 - 15:45 - Getting into trading card collecting and the connection to his sponsor families

• 15:45 - 19:30 - How Dan discovered Collectors.com and decided to join as CTO

• 19:30 - 24:30 - The state of Collectors at acquisition: 750 people, 22 in tech, systems “on fire”

• 24:30 - 27:45 - The approach to transformation: respecting existing talent vs. wholesale replacement

• 27:45 - 34:20 - How to navigate change you’ve never done before: removing fear, defining “good,” and finding the right experts

• 34:20 - 37:40 - The importance of getting that first milestone right in change management

• 37:40 - 44:15 - The board’s concerns during the first year: spending more, moving slower, and nearly being replaced

• 44:15 - 49:00 - Making strategic trade-offs: keeping infrastructure in a closet, manual on-call, short-term vs. long-term investments

• 49:00 - 52:15 - Different levels of transparency: what the board needs vs. what your team needs

• 52:15 - 56:45 - Why Dan only grew by 5-10 engineers while others hired thousands (and why he was right)

• 56:45 - 1:02:40 - The AI journey: starting with one person in 2021, building to 10-15 engineers, launching card scanning feature after 4 years

• 1:02:40 - 1:05:30 - Corporate AI experiments: testing 15-30 tools at once, what works (performance reviews) vs. what doesn’t (financial data)

• 1:05:30 - 1:09:15 - AI as a “how not a what”: always start with the problem, not the technology

• 1:09:15 - 1:12:30 - What gets Dan bent out of shape: when we stop pushing ourselves to be better

• 1:12:30 - 1:13:45 - The acquisition bet: convincing leadership to give him one month to build instead of buying

• 1:13:45 - 1:17:17 - Dan’s “why”: honoring those who helped him and helping others be the best version of themselves

Want more from me?

Substack LIVE Conversations

SAVE THE DATE: Monday, December 22nd at 10am ET for a live conversation with Aamina Awan-Khan about “The Intersection of Identity and Purpose.” Aamina was the former Chief Partnerships Officer in the U.S. Department of State’s Bureau of Public Diplomacy and has held management roles with the Clinton Foundation, the United Nations and Credit Suisse AG. Link to come next week.

If you missed my conversation yesterday with military veteran and philanthropy leader, Maia Molina-Schaefer ( on Substack), stay tuned. I’ll be publishing our full conversation and a written digest next week.

Catch up on all of my Substack Lives here.

Work with me in 2026

And there is still one spot left for 1:1 coaching with me in Q1 2026. I’ve also just recently opened up a limited set of corporate group coaching and facilitation workshops. If you’re interested in either, book a 15 min free strategy call.

May you lead without limits,

Get more from Kathy Wu Brady in the Substack app

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Happy Thanksgiving week!

I’m so grateful you’re here. After a year of writing and all your support, I’ve started hosting Substack Lives because I love showcasing leaders with valuable insights (and I love to gab). You can find all past ones here.

SAVE THE DATE: Monday, December 1st at 11am ET I’ll be with Dan Van Tran, the CTO of Collectors. We’ll be talking about the Reality of Being a CTO in 2025. (Join here)

Now, let’s get into this week’s post:

Your Cheatsheet

• Most workplace dysfunction isn’t a people problem—it’s a system problem.

• In this conversation with Paul Sweeney, author of Sense Labs and Magnetic Nonsense, we explore why organizations keep using the same broken approaches (heroic leadership, rigid performance management, detailed transformation plans) and what leaders can actually do differently.

• Spoiler: The answer involves more experimentation, less certainty theater, and a serious look at how power concentrations are literally killing productivity (and possibly employees).

The Kid Who Saw Dead Ideas Everywhere

Paul Sweeney has had what he calls “a very random career”—from lost baggage handler at an airline to Chief Strategy Officer at one of the UK’s largest companies, with consulting stops in between. But somewhere along the way, he became like the kid in The Sixth Sense, except instead of seeing dead people, he kept seeing the same dead ideas everywhere.

“I just kept seeing the same dead ideas everywhere. I became really curious about why every large company seemed to be the same and to do things that clearly at the macro level were not really working.”

His book, Magnetic Nonsense: A Short History of Bullshit at Work and How to Make It Go Away, dives into why we keep perpetuating practices that don’t work, and more importantly, what we might do instead.

I invited him to join me on a Substack Live because I loved how he was challenging norms that most leaders in business take for granted. It was a fun conversation filled with insights that leaders can put into practice now.

Why We Love Simple (and Wrong) Answers

Here’s an uncomfortable truth: we’re biologically wired for nonsense.

Paul explains that beyond the fight-or-flight response, we have three other evolutionary hangovers:

• “a deep aversion to uncertainty,”

• “a deep need for sense-making,” and

• susceptibility to “simplistic versions of the truth that sound plausible.”

This is why frameworks like Simon Sinek’s three circles get 65 million views on TED. We desperately want to believe that three words can explain all business success, even when the evidence says otherwise.

The problem? Real business success is messy and nonlinear.

As advertising icon Rory Sutherland puts it:

“90% of success in business is messy.
It’s nonlinear. Some of it’s accidental.
But 90% of the effort in business is about pretending that’s not true.”

The Illusion of Control (or Why Your 18-Month Plan Is Fiction)

Let’s talk about transformation programs. You know the ones: detailed milestones, precise targets, Gantt charts that would make a project manager weep with joy.

Paul offers a better metaphor: “Hundreds of years ago, when sailing ships had no engines, captains departing from England never used to say ‘we’re going to arrive in New York.’ They used to say ‘we’re setting off in the direction of New York.’ Because they knew that along the way, all kinds of things could happen that they couldn’t control.”

The alternative? Emergent transformation:

A process of change that arises from the spontaneous, unplanned actions and interactions of a system’s components over time, rather than from a top-down, pre-planned strategy.

Complexity theory suggests that in complex situations, “you have no idea what the cause and effect of your interventions is going to be in advance.” Instead, “try multiple smaller interventions and actually see what works, dial up the stuff that’s working, dial down the stuff that isn’t working.”

Yes, this means you can’t pretend you’re certain about outcomes. But as Paul asks: wouldn’t that actually be liberating?

The Practical Challenge: Navigating Investors and Employees

Of course, two audiences struggle with this uncertainty: your board and your employees.

Paul’s advice is refreshingly direct—have the honest conversation: “Which version of this would you like? The false solution of certainty or the experimental approach, which I think will get us to where we’re going to go. But, you know, I can’t be overly precise on it.”

And here’s a provocative suggestion: “Be a bit more like a pirate. Just go a bit rogue. And then if it goes well, pop up and go, okay, this is what we’re doing. It’s going really well. We’re going to keep going now.”

Make the narrative smaller at the start. Save the big campaign for after you’ve got evidence it’s working.

The 40% Problem: Bullshit Jobs

Here’s a statistic that should terrify every CEO: In surveys of hundreds of thousands of management and white-collar workers asking “is your job entirely pointless and adds no value to the world?” 40% said yes.

Paul calls these “bullshit jobs,” borrowing from the late David Graeber’s work. And last week, Gallup reported that 45% of people feel no sense of purpose at work. Gallup blamed it on employee engagement, but Paul thinks “that’s all backwards. I think that’s because they had pointless jobs. Of course, they’re not going to feel a sense of purpose at work if you realize your job is useless.”

The Industries of Nonsense

Some of the biggest culprits? The very functions designed to help:

• Wellbeing interventions: Research from Oxford University’s wellbeing centre shows that “things like mindfulness training, mental first aiders, duvet days” are “a complete waste of money.”

• Values: Complete waste of time (often just words at best, confusion at worst)

• Culture change initiatives: No evidence they make any difference to company performance

• Employee engagement: The causation is backwards—successful companies are more engaging, not the other way around

There will be “$100 billion spent on” pointless wellbeing interventions “this year. And nobody’s looking at the research.”

The Power Problem (Or: How Good People Become A**holes)

Now we get to the really uncomfortable part.

Paul warns he’s about to use a “rude word,” but it’s necessary: “If you give people a lot of power, like the CEO of a big organization, what the research shows is that even if you were pretty well adjusted earlier in your career, there’s a reasonable chance you’ll become a bit of an asshole, even though you didn’t want to.”

It’s not their fault—it’s the system.

CEOs become increasingly detached from reality. They spend 70-80% of their time in meetings, less than 10% with customers and actual workers.

Over time, they start thinking they’re smarter than everyone else, make decisions that favor themselves, and are more likely to condone unethical behavior.

The Bottom and Middle of the Hierarchy Are No Better

At the bottom: If you take power away from people and subject them to job insecurity, “it’s very detrimental to creativity, to innovation. But also, there’s some research that suggests if you subject them to prolonged periods of low autonomy and high insecurity, it’s more predictive of early deaths than smoking.”

Let that sink in. Your organizational design might be killing people.

As Paul notes, “this stuff never appears on the corporate risk register. The fact that you’re killing your employees, potentially.”

In the middle layers? People “spend most of their time self-promoting and playing politics, and then taking out the fact that they don’t have that much power, taking it out on the people below them.”

It’s The Office in real life.

A Different Model: Buurtzorg

The most fascinating example Paul shared is Buurtzorg, the Dutch nursing organization. The founder was fed up with efficiency consultants giving him a handheld device that said: “Go to this [senior’s] house. You have two minutes to change her bandage, and then you have to get back in your car and go to your next appointment.”

His insight? “What we need to do with that [senior] is maybe I need to call her children to come visit her. Maybe I need to get the neighbors to take her shopping. Maybe I need to make sure she gets to go to her bingo club on a Wednesday night. It’s much more than changing a bandage.”

So he created something radical:

• 1,000 self-organizing teams of nurses

• No middle management in an organization of 10,000 people

• 35 people in the head office doing finance and legal

• 20 coaches who help teams resolve conflict but don’t manage people

• One strategy: “I don’t have a strategy. My strategy is to give the best care we can to the patients. That’s all I care about.”

Could this work everywhere? Probably not. Paul notes that “a lot of people in that nursing community, they just want to be nurses. They don’t want to climb a career ladder and go into management and leadership.”

But there are lessons here about trusting practitioners to practice, rather than managing them into oblivion.

The Performance Management Problem (Spoiler: It Doesn’t Work)

Here’s something that should make every HR professional uncomfortable: performance management “doesn’t improve performance,” but “there’s a lot of evidence that it annoys people.”

Paul spent three years as Chief Strategy Officer and never had a performance review. He and the CEO “just used to catch up every Friday and chat about the week. The idea of doing a performance review would have been really odd.”

A Better Model: Peer-Based Performance

Organizations like Buurtzorg use a radically different approach.

Teams ask themselves two questions periodically:

1. On a scale of one to five, how good have I been at keeping my commitments to the team?

2. How good have I been at taking the purpose of the team forward?

You rate yourself, the team rates you, then you compare.

This approach “fixes the tendency of women to underrate their own performance because they get a boost when the team often rates them higher. And the other way around for men who tend to overinflate their performance.”

The kicker? “If there’s a huge difference between your view of yourself and the team’s view, often people leave at that point without being managed out because they realize that there’s kind of overwhelming evidence that it’s not going well.”

What About Bonuses and Compensation?

Paul worked at a consulting firm where the director made a brilliant move: “All of you are going to get, as your bonus, 2% of the company’s net profits. That’s it. Same for everybody in the team. And now let’s all work together to grow this company.”

They doubled the size of the company in three years.

Why did it work? The director “was smart enough to recognize that serendipity actually plays a big role. You might just be in the place at the right time. Someone you knew got a new job and called you in. I mean, it wasn’t really your fault.”

And critically, “if you don’t have to worry about the bonus stuff, you’re actually paying more attention to doing a good job, I think, than just getting on with it.”

The AI Threat You’re Not Thinking About

We’re all worried about AI taking our jobs. Paul has a different concern: “AI might not be coming for your job, but it is coming for your brain. And it is coming for your independence of thought.”

He has a friend who won’t send an email without asking ChatGPT what to write. And here’s the problem: “If you ask ChatGPT how to run an organization, it’ll just turn out the same stuff that we’ve been complaining about. It goes to the mean, which is the status quo.”

You won’t get critical thinking from a model based on regurgitating the past.

So What Do We Actually Do?

If you’re a leader reading this and thinking, “Okay, but what can I actually do?”, Paul has a starting point:

Start with “doing some critical thinking training for their team, their immediate team.” In Ireland, citizen panels now spend “two or three days teaching them to think critically and how to deal with conflict constructively. And it’s been massively transformational to the outcome of these panels.”

Then: “Get the team away from work for a day or two and do some really good critical thinking training and then challenge the team to pick one thing and try and test a different way to do it.”

For bigger organizations: “Why not take a really small part of this really big company and test something different? … It could be one store, one city, one building, one factory.”

And Paul’s broader challenge to CEOs: “Didn’t you ever get curious as to why the evolution of thinking about organizations seems to have stopped in somewhere around 1965? The way that we structure organizations, the way we think about leadership, the assumptions we make about how to run a company, they haven’t changed since the 60s.”

His pitch: “Now that you’re in this position of power, come on, do something interesting. You just want to be like a dull CEO like everybody else. Come on, let’s go and do something fun. It’s not going to cost much, and we might learn something.”

Your Turn

Here’s my challenge to you: Pick one idea from this conversation and do some research.

Maybe it’s:

• Testing peer-based performance reviews with one team

• Running an experiment with emergent vs. planned transformation

• Examining your bonus structure for unintended consequences

• Investing in critical thinking training instead of another wellbeing initiative

• Canceling or cutting 50% of your meeting time

Have a discussion with your leadership team. See if you want to experiment. Because here’s the thing: as Paul says, “the dysfunction at work” is “generally not the people. It is the system. It’s the structures.”

The architecture goes back to religious and military organizations. It’s held in place by leadership education, governance, regulation, and investor expectations. But “the only way [to change] is for enough organizations to be brave enough to try something different, which is probably easier when you’re not a listed company with all the obligations that comes with that.”

You have more power to change this than you think. Especially if you act collectively.

Learn More from Paul

Want to go deeper into Paul’s work? You can find him at:

• Substack: Sense Labs

• Book: Magnetic Nonsense: A Short History of Bullshit at Work and How to Make It Go Away (Available on Amazon)

• Website: senselabs.co

• LinkedIn: Search for Paul Sweeney (where he’s “annoying lots of people” with his AI bullshit detector GPT that evaluates management consulting reports)

Join Me for another Substack Live

Download the Substack app to join me:

December 1st at 11am ET: “The Reality of Being a Tech Leader in 2025” with Dan Van Tran of Collectors. (Link to Join)

This is a live, interactive conversations where you can ask questions and engage in real-time. Hope to see you there!

Get more from Kathy Wu Brady in the Substack app

Available for iOS and Android

Get the app

Work With Me in 2026

I’m currently booked through the end of the year, but I’m opening up 5 coaching spots for the new year. If you’re a senior leader looking to up-level your leadership, career, and mindset—and you’re ready to challenge some of the nonsense we talked about today—schedule time with me to see if there’s a fit.

Let’s make 2025 the year we take the dysfunction out of work.

May you lead without limits,

Laura is the youngest commissioner in the FDNY’s history, and the first woman to hold the role. But titles don’t tell the real story. Her story is about navigating resistance, listening deeply, and redefining leadership from the inside out.

We met through the Women in Power Fellowship at the 92nd Street Y — a program connecting women who are shaping what leadership looks like across the public, private, academic, and social impact sectors.

What struck me most about Laura wasn’t her résumé. It was her humility. Her curiosity. And her willingness to say, “I’m still figuring out who I am after that job.”

That level of honesty from someone who’s led through literal and figurative fires? It’s rare.

Leadership Isn’t About Having the Plan — It’s About Staying Close to Purpose

Laura laughed when I asked if she’d always planned her path — campaign strategist, public servant, then fire commissioner.

“There’s nothing wrong with having a plan,” she said. “But I’ve never gotten to the next thing because of one. I’ve always followed where I could make a difference.”

What a powerful way to navigate your career.

So many leaders I coach cling to the illusion that career progression is linear — that clarity comes from the next title. But Laura’s story is a reminder that clarity comes from direction, not destination. You follow the feeling of impact, not the illusion of control.

When You’re Brought in to Change the System, Start by Listening

When she first arrived at the FDNY, the department was grappling with outdated systems, lawsuits, and low morale. She was an outsider, appointed by the mayor. “Government doesn’t love outsiders,” she told me. “They see you as someone who’ll be gone in two years.”

Instead of trying to prove herself, Laura started listening.

She rode along on calls, sat in dispatch centers, and listened to 911 operators.

“You can’t fix what you don’t understand.

And just because you know the problem doesn’t mean you know what got the organization there — or what people are afraid of losing if it changes.”

That insight hit home for me. As leaders, we often rush to act when what’s really needed is patience, empathy, and presence.

Change starts with curiosity, not conviction.

The Cost of Care: When Empathy Becomes Exhaustion

One of the most resonant parts of our conversation was about the cost of caring.

Laura shared that her empathy — one of her greatest strengths — sometimes became her kryptonite.

“When someone in the room wasn’t okay, I couldn’t focus until they were,” she said. “As commissioner, that became impossible — I had to make 27 decisions.”

I could feel that in my bones.

I told her how I’ve always been an empath — how my instinct is to sense who’s struggling and bring them in. But leadership often requires sitting in the discomfort that not everyone will feel good in every moment.

Our job is to lead the room, not rescue it.

We both agreed: servant leadership without boundaries becomes self-sacrifice.

The line between empathy and exhaustion is thin, and too many women leaders cross it without realizing they’ve left themselves behind.

The Shift From “One-to-One” to “One-to-Many”

Laura described the jarring loneliness of becoming commissioner after eight years in the department.

“I’d always been the person people came to for advice. Suddenly, I was the person everyone watched,” she said.

“Leadership is lonely — not because you’re alone, but because you can’t unburden downwards anymore. Your words carry weight. People don’t just hear what you say — they interpret it, repeat it, and sometimes reshape it.”

That’s a powerful reminder for any leader transitioning from manager to executive. Your role shifts from knowing everyone to being known by everyone. And that requires a new kind of discipline — one that balances authenticity with restraint.

You Are Not the Organization — and That’s a Good Thing

One of Laura’s mentors once told her something that’s stayed with me:

“Never own an organization’s problems as your own, or you’ll never be able to fix them.”

That’s brilliant advice.

So many leaders — especially women — absorb the weight of their teams, their companies, even their institutions, as if it’s personal. We internalize responsibility that isn’t ours to carry. And in doing so, we lose perspective — and power.

Laura reframed that for me: you can care deeply without confusing identity and impact. You can love the mission without becoming it.

That’s not detachment. That’s wisdom.

Resilience is Built before Crisis and with Community

When we got onto the topic of crises, Laura was emphatic that you can’t build resilience after a crisis; it must be done before.

And the most sustainable method? Through community.

Community-based peer counselors are a part of the FDNY fabric. These professionals have mental health training and deep experience in the uniform.

They build community by making it okay to talk, to seek help, to feel bad about all kinds of things.

These conversations help build resilience individually and as a group. As a result, when a crisis hits, resilience is already part of the system.

The Evolution of the FDNY — and a Lesson for Every Institution

One of Laura’s biggest lessons came from recognizing that the FDNY’s mission had changed — even if its identity hadn’t caught up.

“Eighty-five percent of our calls were medical emergencies,” she said. “Only two percent were fires. But we still talked about ourselves as a fire department.”

That disconnect isn’t just about branding. It’s about survival.

Leaders everywhere face the same challenge: how to tell the truth about who we’ve become before the world forces us to.

Change isn’t failure. It’s evolution. But evolution demands courage — to say, ‘We’re different now. And that’s okay.’

Final Reflections: Leading Without Losing Yourself

Laura and I ended our conversation talking about identity — how to step into the role of leader without losing the person inside it.

She described it beautifully: “When I put on my suit each morning, it was like stepping into the role. But when I came home, I’d take it off — literally and emotionally — and become Laura again.”

That image stayed with me.

Because leadership isn’t about becoming someone else. It’s about learning how to carry your values into bigger rooms — without letting the room define you.

If You’re Leading Through Fire

Here’s what I took from my time with Laura Kavanagh:

1. Follow purpose, not plans. Direction matters more than titles.

2. Listen before you fix. The anxiety you ignore will become the resistance you face.

3. Empathy is a strength — until it isn’t. Protect your energy so you can sustain your impact.

4. Your role is not your identity. You serve the mission, but you are not the mission.

5. Evolve out loud. The bravest organizations — and leaders — tell the truth about what’s changing, and they do it in community to strengthen everyone in the process.

If this conversation resonated with you, share it with another leader who is leading through change or is in a season of reinvention. And if you’ve ever felt the tension between leading fiercely and staying human, you’re not alone.

That’s what Lead Without Limits is all about.

Join me next Tuesday for a Substack LIVE with Kristof Shoenaerts of Job Search Unlocked — 10/21 at 10:30 am ET (link to join).
We’re talking about the 5 things every leader should do before they start their job search. Download the Substack app to join. See you there!

You’ve done the inner work. Now you’re ready to go deeper.
Hiring a coach is a power move — but finding the right one? That’s where most leaders get stuck.

I’ve seen it happen a hundred times.
Smart, thoughtful execs finally say: “Okay. I’m ready for help.”
And then… get lost in a sea of possibilities.

Let me help you cut through the noise.
Here are 7 steps I personally recommend to my clients when they ask:

“How do I find a coach that actually moves me forward?”

Finding the right coach for you doesn’t have to be hard if you know the steps.

Coaching is expensive and time-consuming.
You want to take the search process seriously. But not too seriously.

The biggest mistake you can make is overthinking the process and assuming that you’ll find the perfect person immediately.

It’s far more effective to view the search as a series of experiments, where you’re learning as you go. The search itself is a part of the learning.

Here are the 7 steps that I recommend to friends and clients who are in the market for a coach:

1. Know What You Really Need

This is where 90% of people skip ahead… and end up circling back.

Are you looking for clarity?
Career transition support?
Team dynamics help?
Mindset rewiring?

You don’t need perfect clarity — but get clear enough to sort through the noise.

Start with:

• Your top 1–2 goals

• Your definition of success

• What would make you say: “That was worth every penny.”

2. Try Different Styles

Some coaches push, some probe, some guide.

Ask yourself:

• Do I want structure or spaciousness?

• Do I want to be challenged or supported (or both)?

• Do I want a model or a mirror?

There’s no “right” answer — only what fits your nervous system right now.

3. Get Clear on Your Investment (Time + Money)

Coaching is an investment. In energy. In dollars. In your calendar.

Ask:

• What’s your budget?

• What’s your time capacity?

• Will your company pay for this? (Pro tip: Most will.)

Knowing your boundaries helps you find someone who aligns with them — not someone you’ll grow to resent.

Bonus: If you haven’t asked your company to pay, you’re missing out on a key resource. Most organizations will pay for leadership coaching to drive more effective outcomes.

4. Build a Strong Shortlist

Please don’t just scroll Instagram and hope for magic ✨

Here’s what I tell my clients:

• Ask 2–3 trusted peers for referrals

• Check coaching platforms (there are good ones out there)

• Look for thought leadership — LinkedIn, Substack, podcasts

Start with 5–6 names. Do light research. Trust your gut to shortlist 2–3 for deeper conversations.

5. Interview with Intention

This is not like hiring a vendor. This is hiring someone to walk with you.

Ask real questions:

• What kind of clients do you love working with?

• What’s your approach to change and resistance?

• How do you know when coaching is working?

Do at least 3–4 interviews. Not because you “should” — but because hearing what you don’t want helps you find what you do.

Bonus: Once you’ve found one you like, don’t be afraid to follow up with more questions. This is your chance to learn what you need to know. Don’t be shy.

6. Test Drive

Ask for a trial session or mini-engagement.

Even if they require you to commit to a package purchase, ask if you can get just one or two sessions to start.

You’ll likely know within the first 15 minutes if there is a fit, but if you’re trying to break out of your comfort zones, sometimes you need more time to figure out what works.

7. Allow Evolution

The right coach for this season may not be the right coach forever.

Some coaches work with clients for 3-12 months. Others have coaching relationships that last for more than 5 years. Ask them what they prefer.

Then lean into your own instincts.
You’re the only one who knows what will work best for you.

Pause a relationship or move on when you feel you’ve achieved what’s possible with your current coach.
Keep going if it’s feeling good.

Wait… how long should this take?

Finding a coach is not dissimilar to the search for anyone providing an important service in your life.

If it’s taking days, you might be rushing it.
If it’s taking months, you might be using perfection to avoid a decision.

Take a pause if you need it.

While finding a coach is likely one of the larger investments you’ll make in your career and life, don’t set an unattainable bar.

Be ready to experiment and switch up your coach if you’re not getting the results or experience you hope for.

Closing thoughts.

If you’re ready to take the plunge, don’t wait.

Each month you are delaying your growth is a month you are losing an opportunity to drive greater impact, find a more joyful path, and feel more confidence and at ease.

Coaches can transform not just your work, but your life. But only if you’re ready to do the work.

And if you need help navigating the search? Let me know.

❤️ If this helped, share it with someone else who is stuck. Leave a comment below or reach out — I’m here for questions.

Don’t forget to join me next Tuesday, 10/21 with Kristof Shoenaerts at 10:30am ET for a Substack Life on the 5 steps leaders should take before they start a job search. (link to join)

May you lead without limits,

Join me today — Tuesday, 9/29 at 1pm ET — for a Substack LIVE with Melissa Muth Martinez from Honest Office to talk about interdisciplinary leaders: why they matter, how to find them, and grow them on your team.

He can move millions with one email…
But he hesitates to ask for a stipend for our coaching calls.

She saved millions of dollars and hundreds of lives during COVID…
But she’s still waiting for “the right moment” to ask for a bigger role.

These aren’t outliers. They’re high-performing leaders. Fierce advocates for their teams.
But when it comes to themselves… They go silent.

And I get it — because I used to do it too.

Advocating for yourself is NOT a selfish act.

I relate to these leaders deeply because I was one of them.

Throughout my career, I would find ways to elevate my team.
But when it came to my own role, I would wait or make excuses.

• When I was leading internal operations at a start-up and paid two-thirds of what my colleague was making with a similar scope role, I told myself, “He should be paid more. He’s more experienced than me. Let me prove myself first.”

• When I was overwhelmed leading 4 functions, instead of asking for more resources, I did the opposite. I applied more pressure and said to myself, “You should be able to do it all. You’re just not operating well enough.”

• When my son was struggling with sleep, I had trouble admitting that sleep deprivation wasn’t just draining me, it was killing my ability to function. My narrative was, “Just keep going, you can weather this storm. No one else can do this work, so you have to.”

I didn’t understand how to reframe my needs until I hit rock bottom, and was forced to change my mindset to make sense of what was happening.

It was a profound shift.

Stop seeing your needs through a personal lens.

When leaders zoom out and stop seeing their needs through a personal lens, they make room to start viewing themselves through a leadership one.

The difference?

When you are viewing your needs in a personal context, they feel small, selfish, and narrow-minded.

But when you shift to leadership context, you start to realize that you are a critical resource in the organization. You no longer exist in isolation. You are part of a whole, a very important part.

When your needs are not met, it isn’t just about you not feeling satisfied or supported. You are not able to do your part to make the organization successful.

As a leader, you wouldn’t let your star player be kept on the sidelines or leave the organization because they were overextended or undercompensated.

Why would you treat yourself any differently?

As the leader on the team, you need more support, not less.

Your job requires constant high-stakes decision-making. You are responsible for the direction of the business and for resolving issues when things don’t go your way. You are the culture bearer, and responsible for all the people who report to you.

To do all that well, you need to have sufficient capacity and fair compensation.

If your role is too broad, narrow it.
If you don’t have enough support, add it.
If you are not fairly paid, change it.

Self-advocacy isn’t selfish; it models courage and boundaries for your team.

When you don’t take care of your needs, the cost is far greater than your happiness or your performance. It impacts the entire team.

I had a leader once who didn’t know how to rest. Her overwork wasn’t just a habit, it was part of her brand.

She was amazing in all other facets — visionary, bold, and kind. But this one attribute scared me.

I saw that same overwork in myself — and it scared me. I worried that working with her would make it harder for me to set healthy boundaries. My fear of it was so great that I never ended up following her into new ventures, despite wanting to work with her again.

When you don’t take care of your needs, you are telling your team that it’s OK to not have your needs met. It doesn’t have to be overt, in fact, subtle cues can sometimes be even more impactful, like the leader I loved working with, but didn’t want to follow.

If you want to build a team where high performance is sustained in a healthy way, you need to show the team how to make that happen.

If you want to attract top talent, then you need to be resourced well, so that you can resource your team appropriately.

How to start to self-advocate.

Here are 4 ways to get started:

1. Treat self-advocacy as a leadership responsibility.

Stop seeing your needs as an afterthought and start prioritizing them alongside your other strategic people investments.

Connect your needs to the organization’s mission and goals. For example, if you shed some responsibilities, will that allow you to use your unique talents to accelerate growth?

Make the case to yourself first. You’ll be better equipped to make the case to others.

2. Role-play conversations.

Practicing your message helps you hone in on what matters most. Gather data and evidence for your argument.

If you have a loud inner judge, write down the concerns that come up and be prepared to address each one, but don’t let your inner judge shut you down.

Work with a friend, a coach, or a trusted colleague and have them help you practice.

3. Write down the value of what you’re asking for.

The impact of your ask is likely far greater than the ask. When you write down the value, you are shifting the focus from you to the outcome of the ask.

That simple shift in focus reinforces your shift to a leadership lens.

4. Use the same strategies you’d coach your team to use.

We know the right path when someone else asks us for guidance. Our brain freezes when it’s an issue we are grappling with.

So pretend that your ask is coming from someone on your team. Write down how you’d advise them. Now apply that wisdom to yourself.

Start valuing yourself properly today.

👇 Before you close this tab — do one thing:
Write down ONE need you’ve been minimizing.
Now make a plan to advocate for it this month.

Remember that advocacy isn’t just for you:

If you want your team to believe in their worth, start by believing in yours.

If this post resonated with you, share it with another leader who needs a reminder to self-advocate.

Help other leaders find this post on Substack by clicking on the ❤️.

If you have a tip on how to self-advocate, please share it in the Comments below. The Lead without Limits community will be so grateful.

May you lead without limits,

P.S. Join me today — Tuesday, 9/29 at 1pm ET — for a Substack LIVE with Melissa Muth Martinez from Honest Office to talk about interdisciplinary leaders: why they matter, how to find them, and grow them on your team.

I once had a team member tell me, flat-out:
“We knew you wouldn’t listen. So we stopped speaking up.”

That line haunted me.

Because the truth is... I thought I was open. I asked for feedback. I ran the surveys. I did all the things.

But I wasn’t asking the right questions.

I was fishing for affirmation... not truth.

When you feel like you are drowning in a sea of issues, it’s hard to prioritize inviting more people to share more areas for improvement.

And yet, without these insights, as a leader, you cannot direct your team well.

Here’s the good news: You don’t have to address all of the feedback.
And the not-as-fun news: But you do need to seek it.

One of the most valuable, but underutilized, sources of intel is your team.

They are the people closest to your customers, your partners, and your operations. They know where you’re winning and where you’re missing the mark. They are your best brand ambassadors, and they know where all the bodies are buried.

And yes, I know. You already ask for their feedback, regularly:

You run annual employee engagement surveys.
You create space in your team meetings.
You ask your direct reports in your 1:1s.

Isn’t that enough?
No.

Even if you do all of that — and I bet there are one or two you miss (I certainly did) — you aren’t doing enough.

Why?
Because it isn’t enough to ask for feedback.

Why your team doesn’t tell you the truth.

Let’s be honest. Even if you’ve built trust with your team, most employees, most of the time, have some fear.

The fear might not be about you, but it could be about the company, the industry, their goals, or some other aspect of work.

These fears may not be guiding their work day-to-day but they certainly impact their ability to take risks.

One of the biggest risks for any employee is speaking up and raising concerns.

The “What if’s” are endless:

• “What if they are seen as a naysayer?”

• “What if what they share is obvious and they’re viewed as not sophisticated?”

• "What if the company has no intention of dealing with what they raised, and their point of view puts a target on their back for being out of alignment?”

• ”What if they are viewed as an instigator and troublemaker?”

These are real, valid fears, and can only be counteracted if you, as the leader, choose to tackle them head-on.

Ask these questions instead.

Open-ended questions are great when you have established norms where employees know that raising concerns will not end in punishment. Unfortunately, that’s not most workplaces.

In most organizations, open-ended questions result in silence.

So how do you help your team take the risk and speak up?

Get specific with your questions.

Stop hiding behind anodyne, vanilla questions that make it clear you don’t want to really hear the hard stuff.

Go for the jugular instead.

Here are some examples:

• Where is leadership missing the mark?

• What are the issues you don’t think we are addressing as a company

• What would make our company 1% better?

• What would make our company 100% better?

• What is the easiest change or investment we could make that would have an immediate positive impact?

• What’s a hard change or investment that we should seriously consider because of the size of the impact?

• Why do people leave?

• Why do people stay here?

These questions might feel like you are asking for dissent. But that’s not the point.

They are invitations to help you improve the organization.

What you learn should guide you to make your company stronger, more purposeful, and a better place to work.

What to do with the feedback you receive.

The surest way to create a safe environment where your team will speak up is to have a clear process for evaluating what they share and determining what you will address.

When people see follow-through, they start to believe in the system.

Some ideas on how to make this a reality:

• Create a committee

• Time-bound the evaluation process

• Make the decision criteria transparent (e.g. impact on revenue, impact on expenses, strategic alignment, etc)

• Highlight what you address and close the loop when something is implemented

• Celebrate all the inputs, and especially the ones that are implemented and make a positive impact

You don’t have to start with all of these.

Make it clear to your team that it will be an ongoing process to make employee feedback a priority. Give yourself permission to launch with a v1 and iterate over time.

What do you do if your team raises issues that don’t align with your values or goals?

Every answer is helpful feedback. If you notice misalignment, it’s signal that either:

• Your values and goals aren’t clear enough to the team and/or

• You have team members who likely are not a fit because they don’t agree with your values or your goals.

Start with your current team and prioritize helping managers to align with their employees.

• If there’s a significant disagreement, then it’s time to gently but efficiently part ways. That isn’t retribution for answering honestly. You aren’t penalizing someone for expressing themselves.

• You’re creating an open and transparent environment where misalignment can be addressed and helping your team stay focused.

• For the person who is misaligned, they likely don’t feel motivated by your goals or values. That’s not a great environment for their growth or success. Parting ways will give them an opportunity to find a place that better fits their priorities.

Then look at your hiring practices. Recruiting is the first step to ensuring you are creating a team that is well-aligned on values and goals.

Your job isn’t to be a great place to work for everyone.
Your job is to create a great place to work for people who want to work in your environment with your mission.

• If it’s a hustle culture, fine. You might not be great for caregivers or people who have a desire for significant activities and relationships outside of work.

• If it’s a culture where accelerating business growth is priority number 1, that’s ok too, but make sure your people know and know what’s expected of them.

You might lose some people in the process, but that is the cost of creating great alignment.

The benefit? Your remaining people will move faster and with greater ease.

Key Takeaways

Your greatest source of insight is right within your organization: your team.

Create practices and a culture where you solicit their input, especially their concerns, to help you avoid missed opportunities and to build a culture of shared ownership.

Don’t rely on open-ended questions. Get specific to get real.

Demonstrate your commitment by following through with recommendations that support company priorities and that can be resourced.

Address misalignment by first clarifying your goals and your values. Then work individually and on your recruiting process to avoid future misalignment. It won’t be easy, but it will help your aligned staff work more effectively.

The next time your team falls silent... ask yourself what questions you haven’t dared to ask.

📨 Know a leader who wants to engage their team deeply but needs help?
Forward this to them. Maybe it’ll give them ideas and a helpful nudge.

✋Want more support?
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May you lead without limits,

Mark your Calendars! If you enjoyed last week’s post about my first year as a solopreneur, come join me for my first Substack Live with on Friday, September 19th at 1pm EST where we will dive deep into the journey.

Most managers I know aren’t thrilled with how their 1:1s go.

Even the ones who say they are? Honestly… I think they might be in denial.

These meetings can take up as much as a quarter of your week.

But do they give you that much value in return?

Too often, they turn into something like this:

• A laundry list of topics

• A surface-level review of progress

• A complaint or two

• Some half-hearted advice

At best, they’re a neutral use of time.
At worst, they’re giving a false sense of progress, while masking real issues and concerns.

Still... most leaders keep going through the motions.

They tell themselves things like:

“I don’t have time to teach my team how to get this right.”
“What’s the point? It won’t change anything.”
“These are just for face time — not where the real work happens.”

But that last point is where they really miss the mark.

Every interaction is a chance to shape outcomes — not just business results, but the intangibles too: trust, clarity, growth, and culture.

So don’t settle. Over the next 30 days, reshape one of your biggest time investments — your 1:1s — and make them worth it.

10 Ways to Make Your 1:1s Exponentially More Effective

1. Get Clear on the Purpose

Most leaders try to do too much in their 1:1s. So they end up accomplishing… almost nothing.

Pick one or two priorities for the meeting — max.

That helps your team prepare. It helps you focus.
And it helps both of you walk away with something that actually moves things forward.

Pro tip: status updates, wins, and numbers? Those can live in dashboards or emails.

Use your 1:1 for things that need real-time discussion:

• Gnarly challenges

• Discussing a private people issue

• Delivering and receiving constructive feedback

• Brainstorming or live workshopping an issue or opportunity

2. Set Expectations & Responsibilities

You wouldn’t wing a Board meeting. Why is a 1:1 meeting any different?

Set the expectations early, like:

• Your direct report should send an agenda a day ahead with any prep materials

• Your direct report should manage the time, record notes, and share them afterwards

• You both will come in on time and distraction-free (phones away, notifications off)

• You both commit to being clear and kind. No sugar-coating and no holding back. That will only delay and confuse

• You both commit to ending every topic with a clear decision and next action

When you are explicit about expectations, you reduce stress and anxiety for both of you and give each other more energy to direct to the priority topics.

3. Get Input and Align

After you have shared the meeting purpose and expectations, ask for input: What you might have missed or where they would recommend changes.

You don’t have to agree with their thoughts, but you should respond to each one and thank them for sharing.

This sets the stage for healthy dialogue in the future.

4. Hold Yourself and Your Direct Report Accountable

Now the hard work begins. Unless you hold yourself and your direct report accountable, all of your thoughtfulness will go out the window.

This means:

• Cancel a meeting if one of you isn’t prepared

• Pause if either of you isn’t distraction-free

• Reschedule if you’re having trouble being clear and kind

Use your time wisely and show each other the respect you both deserve.

5. Lean into the Hard Stuff

When you talk about the difficult issues, that’s when you build real trust and depth in your relationship.

For example:

• How are you working together? What isn’t going well? What is? What can each of you improve?

• How is your direct report feeling about their job and work? Use the LifeLabs CAMPS framework.

• What is keeping you each up at night? Are these issues worth prioritizing or should you let them go?

These are the kind of issues you can’t address in an email or Slack message — they are perfect for face-to-face, live conversation.

They are also the types of topics that, when you break through them, you’ll 10x the productivity of your direct report because you’ll reduce their anxiety and overthinking.

6. Zoom Out

Your best people want context.

Let them in on how things are going across the team, the company, the industry.

They’ll start thinking more strategically, and you’ll get more from them — not just in their role, but as a partner in building something bigger.

7. Ask (& Answer) Better Questions

If you’ve set up your meeting well, you’ll have the space to go deep.

Here’s how:

• introduced me to Christina Wodtke’s Four Square model, where she recommends asking about the confidence of your direct report in hitting their targets. This invites a far more insightful conversation than a simple status update

• My mentor, Lisa Gelobter, taught me the power of asking Why 5 times. Sometimes, the issue isn’t an issue at all. Sometimes, the initial issue is just a symptom of something deeper. You won’t know until you ask 5 times

• Invite your direct report to ask you deeper questions. They’ll develop their ability to be incisive and learn from your answers.

Going deep on high-priority topics has a payoff now and in the future.

8. Talk about Performance Now: Theirs & Yours

Waiting until formal review cycles to share performance feedback is like waiting for a health disaster before you build healthy habits.

You’re wasting time, and it only makes it harder to recover after.

Instead, keep a log of feedback and jot down examples (wins and misses) as you notice them. Then, share them in your 1:1s.

Ask your direct report to do the same for you.

Neither of you will be surprised when formal reviews arrive. And you’ll be course correcting as you go.

Bonus question: “How can you better leverage each other’s strengths?”

Exploring opportunities is how you make 1 + 1 = 3.

9. Talk about Their Future Today

Don’t wait until your employee brings in a resignation letter to discuss career pathing and supporting their growth — instead, make time for it every 3 months.

It can feel scary to talk about career paths if:

• You aren’t sure about what career paths are possible at your company, or your company doesn’t have the financial ability to reward growth

• You’re worried you’ll inadvertently be encouraging your employee to seek opportunities elsewhere

• You don’t know how to guide your employee

But the reality is your top talent is already thinking about their next move. You want them thinking about it with you, not around you.

This builds trust and keeps the relationship open — whether they stay, grow, or move on.

10. Regularly Assess & Adjust

Priorities shift, talent changes, and your time and energy go through different cycles.

Every 2-3 months, do a check:

• Are my 1:1s effective and worth my time?

• Are these conversations moving the business and my team forward?

• Does the schedule match my needs (goals, energy, preferred days, frequency, duration, etc)?

Ask your direct reports for their assessment as well.

Stay flexible. Weekly isn’t always better. Monthly with async touchpoints might work better.

Adapt to the season you’re in.

Leveling up your 1:1 meetings is a win-win-win investment.

Improving your 1:1s is one of the highest ROI moves you can make as a leader.

It boosts trust. Sharpens performance. Builds culture.

So don’t let these meetings just happen.

Make them matter.

What’s one thing you’re going to do this month to improve your 1:1s?

Share them in the Comments below.

Thank you for joining me this week.

If this resonated with you, hit the ❤️ on this post so more people can find it.

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May you lead without limits,

They came from my husband, my kids, my brother, my parents—even my plants and my paintings.

When you start paying attention, wise teachers are everywhere. And the lessons they offer can change how you lead, work, and live.

Let me share my favorite ones with you.

The 6 Best Leadership Lessons I Learned Outside the Boardroom

1. Listen, really listen (my husband)

When my husband and I first met, I had just been promoted to Vice President and I was an eager beaver in everything I did.

I wanted to be first in line, first with the answer, first with the win. Of course, that made others feel unheard—including my husband.

Thank goodness he had the hard talk with me with care and clarity. Without it, I would have never become a good listener.

I’m still more eager than your average 40+ recovering-high-achiever, but I’ve long since learned the power of full presence and how that invites richer conversations, more trust, and ultimately, stronger relationships.

Action: Before you go into your next conversation, take a minute to close your eyes and imagine yourself listening, truly listening to the other person. Setting an intention is an excellent way to help you be more present.

2. Perfect is the enemy of progress (my daughter)

When my daughter started crafting, she worked like a tornado and produced piece after piece: a backpack, a dollhouse, a vending machine.

My instinct was to correct her crooked cuts and messy seams. She looked at me, smiled, and said: “No Mommy, it doesn’t have to be perfect.”

In those moments (and there were many), I’d feel a bit small for critiquing my creative and ambitious daughter, and I’d feel fear that my perfectionist tendencies were going to limit her as I felt they at times limited me.

There’s a time to seek excellence—but not when you’re learning or experimenting.

When you default to perfectionism, you run the risk of overthinking, over-engineering, and overworking. In short, you drain yourself of energy and joy and you might block your progress, too.

Action: When you feel yourself seeking to perfect something, first ask yourself, (1) Is now the time to aim for excellence? and then (2) Is my approach for improvement the best way to move us forward or is there another way?

3. Lean into your obsessions (my son)

Obsessions are a sign that you care about something at an unreasonable level. It’s intrinsic, and it often feels unstoppable. You might not know where it comes from, but you know where it takes you in constant pursuit.

My son has had a lot of trains since he was 2 or 3. It has been deep, unrelenting, and not specific to where lived (in NYC or in the suburbs), how old he is (now in his teens), or what his friends are into (none of them have loved trains the way he has).

While his passion has somewhat diminished, it still comes and goes like a hurricane. When it sweeps in, it’s significant, consuming, and makes everything else dim in comparison.

Because of his obsession, he has created Roblox games and studied the entire NYC MTA train system.

I never felt that level of obsession in my career—until now with coaching, art, and writing.

When you find work that overlaps with your obsession, you are always engaged, always energized.

Action: If you have an obsession, consider if there are ways for you to make this your work and income-earning activity.

If you don’t have an obsession, start to explore and see if you can find one. Don’t be surprised if your obsession has nothing to do with what you do today. That might be one reason you’ll have endless energy for it because it’ll be new and exciting for years to come.

4. Know yourself before you lead others (my mom)

My mother was a geriatric nurse before she retired just over a decade ago. She was exceptional.

Patient’s families sent gifts and thank you cards lauding the quality and importance of her care in their loved ones’ final years and moments. They called her an angel.

My mom loved interacting with her clients and their families. Which is why when she was offered promotions to become Director of Nursing, she was quick to decline.

She knew that more money, a higher title, more authority would never make up for the reduced contact with the patients, the people she enjoyed serving.

I couldn’t understand it, but as I progressed in my career, I finally got it. You shouldn’t lead until you know what makes you tick.

As my mom modeled, there are many ways to lead and make an impact. The best way to contribute is to be true to yourself.

Action: Before you assume that a promotion is the right next step, do some self-reflection and have conversations with leaders who occupy those seats. Be honest with yourself, do you want to manage people and shift the nature of your work. And if it isn’t right for you, celebrate that instead of seeing it as a failing. The win is choosing the work that is the most fulfilling for you.

5. When outgrown your surroundings, it’s time to “replant” yourself (my plants)

When I repotted a plant a few years ago, the roots were packed so tight they couldn’t breathe.

This happens to humans as well.

Perhaps your skills have grown beyond your current scope. Or an activity that used to give you energy is starting to drain you.

Sometimes, you simply need to make a change to your routine or how you approach your life or work. But sometimes, it’s a sign that you need to make a bigger change. You need more space, new nourishment.

Don’t be afraid to make a shift and find a new home. It might feel daunting, but it might also be the exact reset you need to get you excited about your next chapter.

Action: Do an energy and engagement assessment, similar to the one that Bill Burnett and Dave Evans recommend in Designing Your Life. But broaden the scope to include your surroundings and activities outside of work. And then experiment with smaller changes to see if you can experience a shift. If don’t see a change after a more extended period of time (perhaps a month or two), it might be time to make a bigger change.

6. Starting over is just another chance to get it right (painting)

Wiping away your work is essential in oil painting. All the masters did it.

For me, it felt super scary to wipe away my work as a beginner again this past year.

“What if I couldn’t recreate the work again? What if my next attempt wouldn’t be as good as my first? What if I’d never make it good enough?”

What these fears didn’t allow me to see was the simple truth:

Until I wiped away the less-than-stellar work, I couldn’t produce anything better. You have to make space for your improvement.

Now, I trust the process. I know I’ll eventually get it right.

Action: Is there something in your work or career that doesn’t feel right? Instead of plowing forward, take time to reflect. Consider diving in deeper. Exploring this with a colleague or coach may help you get past your fears and more quickly explore potential paths.

These lessons didn’t come from a promotion, a title, or a strategy session.

They came from everyday life—and they’ve shaped me into a better leader, coach, and human.

Leadership wisdom is everywhere if you’re willing to listen for it.

If this resonated with you, share it with someone who’s growing their leadership too.

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And if you’re ready for deeper, personalized coaching, I have one spot open this fall. Book a 15-minute complimentary Strategy Call.

Thank you for joining me this week.

May you lead without limits,

Have you ever had an employee that just wasn’t able to do the job?

Most leaders have.

And most leaders fail to address the problem. They make a ton of excuses.

I know, I’ve made the same ones:

• “I’m too busy”

• “Maybe if I give them a little more time”

• “Perhaps it’s me — I’m not being clear enough or supportive enough”

• “Yes, it’s been multiple tasks, but perhaps I need to just find something else for them to excel at”

• “Hiring a new person is so much work. And they might not work out either”

We think that if we just give it more time, the employee will turn around. And while that might make sense for some employees, it does not excuse us from giving direct feedback and escalating our approach toward exit if we don’t see improvement.

What we don’t realize is happening as we wait, is that we are not only hurting the performance of our team and all the teams around us, but we are damaging our hard-earned trust from the employees who are our stars. Counterintuitively, we are even hurting the employee who isn’t performing.

It takes a lot to make a manager give up on an employee.

Wanda threw her hands up wondering why she bothered.

She had just left yet one more meeting, perhaps her 20th, with a member of her team, Julian, who just couldn’t seem to take direction from her without asking irrelevant questions and questioning her authority.

Wanda was a VP at a consumer brand. A rising star.

Earlier this year, she inherited a team when her boss wanted to increase her scope and influence and added a new group to her purview.

The team consisted of 5 people, each with different skills and tenures.

Overall, most of the team was responsive to her leadership. They welcomed her direct but empathetic communication style and saw her as someone who could elevate the performance and recognition of their team.

The only exception was Julian.

He was the longest-tenured team member and considered the most expert team member. Wanda didn’t receive a detailed overview of the team she inherited because her predecessor had left the company before she took over and her boss didn’t want to influence her views.

So Wanda had the benefit and the challenge of developing her own view.

Early indications were not good.

Right from the beginning, Wanda got indications that were concerning.

Julian would miss deadlines and not communicate in advance. He would not answer basic questions about his workload or be able to summarize his progress and learnings when Wanda asked for more details.

When Wanda assigned him new projects, he would spend 15-30 minutes asking her questions about the assignment, often adding comments insinuating that the initiative may not be needed and that he felt she needed more data before assigning him the work.

Over time, Wanda would find that peers were finding it challenging to work with him as well.

He was also not responsive to their needs and often resisted collaborating. He would instead ask others to send him memos and then respond with more detailed questions. When they asked him to meet live, he would often say he was too busy.

In a fast-paced culture that valued live discussion and collaboration, Julian’s resistance was creating roadblocks and generating frustration.

From bad to worse, and yet sometimes, leaders will still find a way to avoid a negative confrontation.

As team morale dipped because projects were being delayed by Julian’s lack of engagement and missed deadlines, Wanda chose to spend more time with him with the hope of helping him turn around his behavior.

She tried to be patient when he asked his multitude of questions and addressed his objections to her assignments point by point.

Wanda didn’t want to assume he couldn’t do the work. She asked Julian if there were other things happening in his life that were causing him to miss deadlines and decline meeting with his teammates.

Julian shared that he was caring for an aging parent and that might have contributed, but that mostly he didn’t feel his behavior was a detriment and he would try to improve.

Julian’s responses were insufficient — he wouldn’t take responsibility and would offer up excuses or point the finger towards others, but Wanda felt empathy for his situation. She wanted to give him a chance.

She also didn’t want to rock the boat. She had seen other leaders move swiftly to remove tenured staff when they took over and she didn’t like the fear that was left in the wake of their actions.

Instead, Wanda encouraged Julian to engage more with his colleagues, and she gave him feedback on his most egregious misses. But if she was honest with herself, Wanda was not being as direct as she could be. She was certainly not consistent in her feedback. She would provide it sometimes, but not others, and it would often be wrapped in positives.

Wanda also didn’t want to alert her manager or HR because she knew that once she did, they would encourage her to move faster. She wanted to have more time to assess the situation, more time to see if she could get Julian to change his approach.

In addition, Wanda was feeling stretched. She saw hiring and onboarding as a lot of work and she was worried about losing legacy knowledge.

But after another 2 months, it was clear that the projects where Julian was assigned were moving at 50% or slower the pace they needed to and that Wanda knew was possible. Julian was also further solidifying his reputation as difficult to work with and not sharing any context with Wanda as to why.

When the pain is unbearable, we finally take action. But the negative impacts may have already taken hold.

Fast forward one year later and Wanda finally exited Julian as part of a reduction in force — a layoff.

Within a week, Wanda could see the team functioning better. The team was able to move through work faster and she felt more focused as their manager. Wanda literally felt a weight lift off her shoulders as her team was less frustrated and she felt she was no longer wasting her time trying to help a team member who wasn’t open to or perhaps capable of addressing her feedback.

But despite all of these positives, there was significant damage done while Wanda waited nearly a year to exit Julian:

• Julian’s team missed their targets for the past year, impacting everyone’s performance reviews and compensation decisions

• Two top performers left the team when they saw that Wanda wasn’t going to make a decision and it would impact their futures

• Wanda had also lost the trust of some peers and some of her team. They just didn’t understand why she waited so long

The worst part? Wanda didn’t even realize some of these impacts were a result of her delayed decision-making. She had damaged her reputation, and she wasn’t even aware.

As leaders, our responsibility is to the team and to the mission — not to individual people.

Sadly, what Wanda lost sight of during this extended period, where she did not hold Julian accountable for his behaviors and take decisive action was her responsibility to the broader team.

As leaders, our job is to set a clear direction, and resource and direct our teams well. When you leave an underperformer on the team, you are enabling a weak link to weaken the entire team.

What results is a cascading effect with lasting negative impacts:

• Top performers will feel unsupported and leave

• Team operational and cultural cohesion is damaged

• Your time is not optimized, but neither is your team

• You are distracted and not focused on what will strengthen your team

• You inadvertently sow doubts across the team about your collective ability to succeed. Strong positive mindsets lead to positive outcomes and the reverse is also true

And what about the person who isn’t performing?

You aren’t helping them either.

If you are concerned about whether you are hurting their feelings, damaging your relationship with them, or adding stress to their life, well chances are you are doing all of the above, and worrying about it won’t make it better.

They likely know they aren’t performing well, but they are confused about why you aren’t addressing it. In addition, they aren’t doing well in relation to the rest of the team and so they are building a negative reputation. It’s a form of character assassination — they are doing it, but you are enabling it.

You are creating more stress for everyone — you, your team, and the individual underperforming.

It’s a recipe for disaster.

The solution?

Setting clear expectations and communicating directly and consistently about them. And setting milestones by which if you don’t see sufficient improvement, you shift gears and exit the person.

No one wins when you wait to give feedback or to fire someone who isn’t a fit for the job — either because they aren’t performing or if they simply aren’t a fit for the role because of misaligned values or skillsets.

To be clear, I’m not suggesting that you fire someone for a few misses or that you don’t allow for ebbs and flows of performance.

What I am referring to is when there is a clear pattern of behavior that negatively impacts the performance of the team, and after you provide direct and timely feedback, the individual continues to demonstrate a combination of a lack of accountability or inability to remedy it.

When you don’t address these situations quickly enough, you are setting up your team and yourself for failure.

OK, I’ve convinced you that you should not leave an underperformer on the team.

So what should you do?

First, know that compassion and maintaining strong performance standards are NOT at odds with each other. You can do both by creating reasonable standards and by communicating them clearly and consistently.

How to Reflect

Take time regularly to step back from your day-to-day activities. No, not on your nights and weekends — during working hours.

Why reflect?

• You need space to integrate your observations and to ensure that you are not reacting to your emotions.

• It’s natural to feel fear, frustration, and impatience, but those will not help you clarify your approach.

• Giving yourself anywhere from an hour to two to three hours will help you have the space you need to create a strong decisive plan of action.

How do you reflect?

• Change your context — Go to a different location than you typically work. Shifting your setting will help you shift your thinking patterns. Research indicates that a natural environment might be particularly beneficial (University of Tennessee research study)

• Get moving — Research shows that our cognition significantly improves after our bodies are physically moving. Even a 10-minute walk on a treadmill in a windowless room can improve our creative thinking. (Stanford University research study) And while setting standards and communicating them might feel less like creative thinking, it might be exactly what you need to help you loosen your fears on this work.

• Meditate — Quieting your mind will help you feel a bit of distance from the issue and perhaps give you more insight into both what really matters and how to address it.

• Journal — Taking the time to write down your thoughts can help you connect the dots. You might not see it in one sitting, but as you revisit the topic over time, you can read your prior thoughts, and seeing your progress (or lack thereof) on paper can be incredibly clarifying.

• Get input from others — You don’t have to do this work alone. Talk with your boss, HR, conduct a 360 review to get input from peers, or seek outside input from a coach. Asking for help is not a sign of weakness, it’s a sign you are resourcing yourself well.

• Change your perspective — One way to do this is to pretend you are helping a friend with this issue. What would you tell them to do? Another is to jot down all of your strongest assumptions and then flip them on their head and get curious about how you react.

Reflection Questions

Here are some prompts to help you reflect more deeply. Notice that I’ll focus on the role and how the person behaves and how they impact the business.

I avoid analyzing why they are doing something because there is no way to really understand what is going through their mind. Instead, focus on the following concrete questions:

• What outcomes does the role need to drive?

  • How is the person performing in relation to these?

  • Have you given feedback to them on their performance?

  • How long has it been since you provided feedback to them? Has their performance improved?

• What skills are needed to be successful in this role?

  • How is the person demonstrating these skills?

  • Have you given feedback to them on their performance?

  • How long has it been since you provided feedback to them? Have their skills improved?

• What behaviors are important to the productive functioning of the team?

  • How is the person exhibiting these behaviors and what is their impact on the productive functioning of the team?

  • Have you given feedback to them on their impact?

  • How long has it been since you provided feedback to them? Have their behaviors improved?

• Have you set clear expectations on how much they need to improve on the above and by when?

• Are you seeing sufficient improvement at a sufficient pace to give them more time?

Your Action Plan

Depending upon your answers to the above, you may need to take any of the following next steps or a combination:

• Get more information from the person or from others to verify your assessment

• Clarify or update your expectations on outcomes, skills, behaviors, and improvement timeline

• Provide more direct and timely feedback

• Adjust their role to scale down their negative impact while giving them time to improve

In most cases, the worst action you can take is to wait.

If you find yourself landing on “wait” as your path forward, I recommend you step away from this for a day or two and repeat the reflection process.

You don’t have to fire a person immediately when you see challenges, but you do need to address the challenges head-on and as quickly as possible.

To be truly compassionate to your team, the person in question, and yourself, you need to deal with the issues you see.

It won’t be easy, but it is the responsible thing to do.

I’d like to hear from you

This one may be hard to comment on because of privacy issues, so I won’t ask for any specifics. Perhaps instead you can share

• How you make time to reflect and assess the members of your team

• How you stay proactive in addressing issues you observe

Looking forward to hearing your comments and suggestions!

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Donna knew something was wrong when she got the 6pm email from her boss asking for a last-minute morning meeting.

Louis was thoughtful, prepared. He didn’t do last-minute.

When we spoke the next day, Donna was exasperated and confused. She was still trying to make sense of what Louis had shared:

Another of Donna’s direct reports, Sheryl, had gone around her and shared negative feedback about her leadership style. This time it was to Louis, the CEO.

Another of Donna’s employees, Lydia, also shared criticism of Donna on the way out in an HR exit interview. Donna was surprised, but she felt it was to be expected that someone who was let go for performance issues would be upset.

Sheryl was a different story.

She was still on Donna’s team. Sheryl had been in tears when Louis passed her in the hallway and offered to speak with her. That’s when she shared that she felt Donna could be dismissive at times and harsh in how she communicated decisions.

“I just don’t get it,” Donna confided in me. “I ask for feedback all the time. And now Louis is starting to see a pattern that I swear doesn’t exist. What do I do?”

That’s when I shared the hard truth:

Most leaders don’t get feedback.
Not because their team thinks they’re great…
But because their team doesn’t trust them.

This wasn’t just an unfortunate meeting with her boss. This was a red alert that Donna needed to prioritize and address quickly.

The first time your boss raises something, it’s a conversation. The second time is a warning.

Louis had been respectful, but he also didn’t sugarcoat the situation. He was concerned. Donna was a critical leader on the executive team. They couldn’t afford distractions like this.

The biggest issue wasn’t that there was employee disgruntlement. It was that Donna didn’t seem to be aware that it existed and didn’t know what to do next.

Her lack of clarity scared her. Losing Louis’s trust scared her even more.
Like many high-achieving executives, she was stretched thin and pushing herself to the brink.

Donna inherited the Product team at a profitable, growing SaaS technology company a year and a half ago. She was excited to join a company with strong prospects and solid financials. Louis and the rest of the C-suite were strategic and gave her a wide berth to set up the function.

Donna chose to take her time to assess each person on the team instead of going with her initial instincts about who would work out and who wouldn’t. She didn’t want to rush, and she wanted her decisions to be based on sufficient evidence.

Once she had the data points she needed, Donna didn’t waste time reshaping the organization. She let go of 50% of the staff, promoted one, and hired in several new people.

Unsurprisingly, she left some scars in her wake. Some of the team felt she didn’t fully consider their input when she made a decision. Some felt she was too busy to support the team fully.

But none of them told her this was how they felt.

Instead, when she squeezed in a question at the tail-end of a 1:1 meeting or a group meeting, her team stayed silent.

The negative feedback from Sheryl felt particularly unfair. Donna had explicitly checked in with Sheryl after she made a decision Sheryl wasn’t aligned with earlier in the week. Sheryl had made it clear that she was fine.

If Donna couldn’t trust her people to tell her what they actually felt, and there was a risk they would go above her to her boss, how was she ever going to feel safe to more bold moves?

What you crave from your team is often a reflection of what they need from you.

Donna didn’t realize it, but she had hit upon the core issue holding back her team. It just needed to be flipped.

It wasn’t about her trusting her team.
It was about her team trusting her.

They were never going to give her direct, candid feedback if they didn’t trust her. The trust she wanted was exactly what they were seeking as well.

The top reasons why why people don’t provide feedback:

1. They don’t feel safe.

2. They don’t feel safe.

3. They don’t feel safe.

4. They don’t feel there is a time or place to deliver it.

5. They aren’t sure how to frame what they are saying productively.

Those weren’t typos. 80% of the time, people simply don’t trust that their leader will respond well to constructive criticism. And honestly, most of the time, they are right.

Even the last two items relate to not feeling safe. If you are confident that your leader will be curious and open-minded, you’ll find a time to speak to them and you will worry less about delivering it perfectly.

Sadly, too many leaders are so insecure themselves that they are defensive, don’t listen actively, and aren’t able to create the space for someone on their team to share.

Donna wasn’t one of those leaders. She genuinely wanted to know what her team thought, and she regularly asked for their thoughts, but clearly something about her approach missed the mark.

Don’t assume your employees feel safe. Actively create safe conditions.

How you respond in any situation becomes how people expect you to respond on all situations.

If you have a tendency to be impatient or be distracted in conversation, or maybe you cut people off, don’t be surprised that people are wary to share deeper, high-risk thoughts with you.

I’m not saying you can’t demand excellence from your team.

You can and should set expectations that they come in prepared, and that time is used effectively. But if your first response to someone not landing a point is to judge instead of getting curious, you might be setting the stage for them to feel unsafe.

Accessibility is another critical blocker to safety. If you make it difficult for people to book time or make people feel rushed, it’s much harder to dive into difficult topics.

It’s easier to avoid the topic than to try to squeeze it in.

Shifting perception requires sustained, substantial behavior changes.

To help her people feel safe and make her commitment to making space to hear their feedback feel real, Donna had to show she was willing to invest her most precious assets: her time and her attention.

Here was the plan:

• Set up dedicated, quarterly meetings that were 45-60 minutes long to gather feedback

• Be clear about the purpose: to get at the gnarly topics that we unconsciously avoid or are just too scared to tackle, including constructive criticism of how Donna led the team

• Give her people 2-3 weeks notice so that they had time to prepare

For the first meeting, I recommended 3 topics to get the conversation started. She could adjust the agenda as needed based on what her team raised, but it was essential to help set the tone:

1. Decision-making (in your department at the leadership level)

2. People dynamics, specifically the 3 C’s: collaboration, communication, and conflict management

3. Where do they feel confidence? Where do they feel concern?

In the meeting, the leader needs to continue to model curiosity and give your team space.

• Ask open-ended questions

• Get comfortable with silence. That signals patience

• Only give examples when they aren’t sharing for over 5 minutes

• Focus your full attention, no devices. You can take notes with paper and pen, and let people know that’s what you’re doing. Consider assigning a notetaker as well so that nothing is missed

• Orient your eye contact and body towards the person speaking

Let the conversation go where the team takes you. If you need more time, schedule more.

Why a new rhythm is so important.

When you are trying to land a new message, especially one where people may have fear and doubt, you need to make the change feel significant.

The new meeting structure was exactly that:

• A pause from the flow of operations

• Addressing topics that can feel scary head-on

• A moment to show how you as the leader are deeply focused on what each person is saying and nothing else

• Dedicated time so that you can dig into topics deeply

• A group setting allowing for everyone to feel in the know and not be worried about side conversations

Success isn’t how many complaints you receive. It’s a more seamless dialogue between you and your team.

You might get dozens of concerns, and you might only get 2.
The quantity doesn’t matter.

What matters is if your team walks away feeling confident that you will respond to difficult topics well, and as a result, they no longer withhold information and instead share it more effectively and efficiently.

The best teams aren’t the ones that get everything right. They are just better at identifying critical issues and course correcting faster. You can only do that if you trust each other and are willing to talk about challenging topics.

For Donna, the payoff was no longer worrying what her team thought. They didn’t hold back their thoughts, and their ability to navigate dissenting opinions led to only stronger outcomes and greater trust for the entire team.

The real win was that the Product team was making bolder moves, learning faster than ever, and showing all signs of having fun while doing it.

And Louis? He hasn’t sent a surprise calendar invite in months.

Your Turn

Have you struggled to get honest feedback from your team?
Share your story in the comments — I read every one.

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