Three months into my second COO role, I got appendicitis.
I’d like to tell you it was bad luck. But I knew better. I’d been running at a pace that wasn’t sustainable from day one — convinced that proving I belonged meant doing everything at once.
Client conversations. Negotiations. A new employee evaluation process. A pricing model. Hiring. I was also trying to assess what the business actually needed most. But I couldn’t do it well, because I couldn’t do any of it well. I was doing too much.
My body made the decision my ego wouldn’t.
And here’s the part that still embarrasses me a little: when I came out of it, I worked harder. I didn’t see the appendicitis as a signal. I saw it as a distraction, something to push past so I could get back to proving myself. And the crazy thing is, it wasn’t my first time.
I carried that spiral of worry and reactivity for the rest of my time in that role. It was only after I left, with some distance, that I could see clearly: I didn’t need to be more reactive. I needed to be more strategic.
Years later, I watched a friend walk the same road.
She was the new CMO of a SaaS company serving industrial businesses. New industry, new product, but not a new function. She’d built marketing organizations from scratch before. She was ready to do it again.
She’d spent those first months mapping the marketing strategy, aligning with the executive team, and scoping the key hires she needed. Deep work. The right work. But when the company launched a new product, she couldn’t resist. She weighed in at every phase of the planning process, drawing on years of product marketing experience.
Then: silence. No feedback. No engagement. The launch kept moving without her.
She didn’t know whether to push or wait. The clock was ticking. Meanwhile, the hiring process was taking more than she’d expected. She felt stretched thin. And as the fatigue built, so did the fear that she wasn’t doing enough.
That’s when she called me.
My first question was simple: What does your boss actually need from you right now?
She paused for three full minutes.
That pause told me everything. She’d been operating on two assumptions she’d never examined: that she already knew what mattered to her boss and the leadership team, and that the answer to her exhaustion was more effort, not less.
She wasn’t unusual. Neither was I.
We’d both swallowed whole exactly what our culture tells new leaders they’re supposed to do.
Have a 90-day plan and execute it with precision.
Be omniscient about the future and make fast, quick-win decisions.
Show immediate progress and build the foundation for long-term trust.
Model healthy behaviors and work around the clock.
It’s BS. And it will kill your ability to do exactly what matters most: be the strategic leader the organization needs.
Every organization has the same core strategic context
In most organizations, there are only five things that matter most:
(1) Who is the customer?
(2) What needs are you solving?
(3) How well are you doing it?
(4) How are you doing financially?
(5) Who are the key players, how are they performing, and how strong is your relationship?
To be fair, that is a lot to digest, but it’s really what matters most. Your role, your team’s role, how you are structured as an organization, all of that must fit into the above. If you have a good understanding of these elements and if your leadership team does as well, you’re pretty far ahead of the game.
I know this because I got almost every one of them wrong.
Unfortunately, most leaders, when they start a job, don’t focus on these elements. They dive into the minutia of their department and zero in on small details. Those details are super attractive because they are fully in your purview and give you a chance to feel you’re making a mark. But they are a distraction.
When you don’t focus on the right things, you run the risk of setting the wrong strategy and simultaneously running yourself into the ground.
Remind yourself of what matters most and let the rest go
When it came to my CMO client, checking her assumptions changed everything.
She discovered that not only did folks not expect her to do any product marketing work yet, their departments weren’t ready to receive it, hence the silence. And when she checked in with the CEO, it turned out she was doing more than enough and was focused on exactly what mattered most: setting up a strong marketing strategy and creating the capacity to execute on it.
Everything else she was worried about was a distraction.
The relief she felt was immediate and rejuvenating.
I didn’t get that relief in the moment. I got it years later, sitting with enough distance to finally see the pattern clearly. Which is part of why I’m writing this now.
The REAL new job checklist
The moral of the story is to stay focused on the fundamentals and take time to align on what the job expectations actually entail. Here’s what that actually looks like — and what I wish I’d done differently.
(1) Who is the customer?
If you have more than one segment, understand why and what differentiates them. Don’t just operate in the abstract; dig into specific examples.
In my COO role, the industry was entirely new to me. I read up, attended conferences, spoke to customers. But I never gave myself permission to go deep enough. I kept thinking: I should already know this. If I don’t, customers won’t trust me. So I faked fluency instead of building it. And faking it didn’t get me closer to our customers. It took me further away from the kind of empathy that would have helped me assess our situation more strategically.
If you can, talk directly with customers. If you can’t, spend time with the people at the organization who do. Customer empathy is what differentiates those companies that can anticipate the market and those who have to react to it.
(2) What needs are you solving?
Do you understand the pain points your organization is solving? What is the ROI for your customers? Is this a one-time issue or a recurring one? Do you know what success looks like?
I could have done more customer discovery conversations early on. Our product market fit wasn’t bad, but it wasn’t optimized either — and I didn’t go deep enough soon enough. I just assumed it was sufficient because we were closing deals. Closing deals felt like proof. It wasn’t.
If you can’t describe these elements clearly, there is a real risk of product-market fit issues, or you simply aren’t going deep enough to understand the issues. It doesn’t matter if you don’t work in sales, product or marketing. These are the kind of issues that affect very department because it affects the core of the organization.
(3) How well are you doing it?
This isn’t about your team. It’s about the company as a whole. Where does the organization meet or exceed the needs, and where is it coming up short.
After we had more than two dozen customers, I didn’t pause to get real feedback. I wanted to keep pushing for growth. So we were operating and growing based on assumptions rather than verified knowledge. It didn’t show up as a miss right away. It showed up later, when we were trying to grow our sales team without a strong enough playbook. That playbook should have been built through a deeper assessment of how we were actually performing. By not building it, we slowed our progress by more than three years. This is where rushing can actually slow you down.
Why zoom out so broadly when your team only contributes to a portion of the solution? Because you’re a leader. Your job is to think bigger than your function. A different perspective — 30,000 ft or 10,000 ft or 5,000 ft — results in a different set of objectives and priorities. Being able to see each and then align as a leadership team on which one deserves your attention the most is how you calibrate appropriately.
(4) How are you doing financially?
The best leaders know that money creates or constrains opportunity. When you understand your financial reality, you have a greater grasp of what is possible.
I was so focused on minimizing spending and growing revenue that I didn’t realize I could be making strategic investments to lay the foundation for growth. It was narrow-minded — and if I’m honest, it was rooted in fear. Knowing when to invest is as important as being frugal with spending. My fear blocked that insight.
Regardless of which way things are trending, functions that identify opportunities for growth have a far higher likelihood for greater investment. Understanding both — the current constraints and the future opportunities — that’s how you create a strategy that is grounded in reality and reaches for the stars.
(5) Who are the key players, how are they performing, and how strong is your relationship?
Your people are your greatest asset. Especially in the age of AI.
Relationships are a superpower for me. I was able to build strong ones internally and externally. But the gap in my case was that I became overly anchored on the feelings of some of the team, and let that distract me from my broader leadership responsibilities. Building connection through respect is important. Overly anchoring to the need to be liked is not. That is where I fell short on this one.
Understand why your team matters and make sure they do as well. Set clear expectations for success that are both outcomes and behavior-driven.
Make the ones that are meeting the mark feel seen and valued. Make sure the ones that aren’t know where they stand quickly and clearly. If they can’t improve, move them out. This isn’t just for your sake, it’s for theirs as well. A person in the wrong role will not only not deliver, they’ll feel terrible about it to. Do them and the organization a favor, don’t hold on too long.
Develop your employees, pay them fairly, and create an open, two-way dialogue so that neither of you is ever caught off guard when an issue arises. When you have that type of relationship, you’ll create an organization that people will flock to and stay with.
(6) Stop assuming, start verifying
When in doubt, ask. Don’t fall into the trap my friend did — or the one I did — and let your fears and assumptions drive your actions.
Instead, ask your boss, your board, your customers, your team. Don’t let the stories you make up in your head guide your decisions. Get the input from the source and then decide what to do next.
(7) Make time for what’s most important and let the rest go
If you’re starting to feel overextended, don’t treat that as a sign to do more. Use it to find a way to focus instead.
Those first few weeks and months are important not just for setting direction and establishing relationships, but also for creating an operating rhythm that is sustainable.
Burn yourself out by trying to do too much, and you won’t just be too tired to do the work; you won’t have the mental energy to do it well.
Starting a new job is the beginning of a marathon
If you’re fortunate enough to have found a role worth taking and are about to start your next gig, adopt the right mindset. Don’t get swept up by the tumult of the first 90 days. Instead, see the beginning as it actually is: the early moments for a long run.
What matters most is understanding and setting up a roadmap so you know where you are headed and why, and creating the foundation so you can sustain the work. The pace you choose is as important as the focus of your effort. Choose both wisely, and you’ll make progress on what matters most and be able to enjoy the process instead of slogging your way through it.
And if you get a little lost along the way, don’t let your ego keep you charging ahead. Pause and ask for directions. Get input. It’s not a sign you’ve missed the race. It’s a sign that you’re committed to finding your way wisely and with help when needed.
I wish someone had said that to me three months into my COO role. Before the appendicitis made the decision for me.
Success may not be predictable nor guaranteed, but you can set up the conditions well for yourself right at the start so that it’s more likely than not that you reach the key milestones that will signal you are well on your way.
Your turn
What has helped you start a new job on the right footing? Have you ever had to change course and what allowed you to do so? I’d love to hear what you recommend in the Comments. Sharing what we’ve learned doesn’t just help others, it helps reinforce our learnings so that we don’t lose them going forward.
And if you know of someone who is starting a new role, consider forwarding this to them to help guide their early moments on the job.
May you lead without limits,
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P.S. If you’ve been wondering if it’s time to make a change in your career, but you haven’t figured out either what or how, the Career without Limits Retreat might be for you.
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