Who You Work For Matters More Than Any Other Factor in Your Career
A great boss will help you go further, faster, and win bigger than you thought possible.
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Linda was a successful pharmaceutical exec. Three promotions in six years. That’s rare. Very rare.
On paper, it looked like she just picked the right department at the right time.
But if you knew the inside story, you’d know it wasn’t just the company. It was her boss — Brad, the CMO.
Brad was a wunderkind.
He graduated with honors. MBA at 19.
Climbed the ladder in a major tech company. Got poached by a CPG giant. Launched several brands. Then pharma came calling.
Brad was a unicorn — a visionary who could execute.
Built strong teams. Attracted top talent. Gave clear marching orders — then total freedom.
Feedback? Brutally direct. But fair. And kind.
When one employee had to care for a sick parent, Brad didn’t blink — flexible schedule for months so they could keep working and be there for family.
Linda frankly got lucky working for Brad.
She earned the role, no question. But she barely knew Brad when she started. She researched the company. The products. The strategy. But not the boss.
Over six years, she appreciated Brad’s style — but didn’t realize how much she was absorbing from his leadership. She didn’t see how often he was modeling leadership — right in front of her. She didn’t know that when she stumbled, he could have stepped in — but didn’t. He let her figure it out.
Linda also didn’t realize the pace of her promotions wasn’t normal. Brad had been pulling strings — in the best way.
Sadly, she learned the hard way — a few years later. She took a bigger title at another pharma company…
And her new boss? The polar opposite. Toxic. Distrusting. He nitpicked every win, ignored her ideas, and made her dread 9am.
Five years. Zero promotions. Bad habits creeping in. Confidence shot. Burnout brewing.
Linda could still change course. But five years of stagnation? That’s a steep price to pay for not vetting your boss.
Finding a great boss is the most important part of finding a great job.
It may seem surprising that your boss matters more than the industry or function you choose.
But the reason is simple: the best bosses are strategic about the organizations they choose to join.
They maximize the opportunities to win, and you will benefit from their wisdom and their due diligence.
They won’t always get it right, but they will always try to do right by you so your risk is lower even if they make a mistake.
1. Know what you’re looking for great boss.
Many qualities can make for a wonderful person to lead you, but these are some of the most essential:
Excellent at setting goals
Delegates and prioritizes well
Recognizes and rewards their team’s work
Committed to their team’s growth and success
Has a track record of people growing in their team and beyond
Manages up well and secures the resources their team needs to win
Communicates directly and doesn’t shy away from tough conversations
Attracts and hires people who complement them and their teammates
Possesses these traits: focused, ambitious, kind, curious, accountable
For more senior leaders, they are first and foremost excellent strategists: able to read the tea leaves, anticipate customer and market shifts, and understand people and power dynamics so that they can position themselves and their teams well.
These people are rarely caught off guard, distracted, or fall behind. When you work with a leader like this, they will create the tailwinds that will help you advance.
2. Due diligence your boss, just like they background check you.
When you get the offer, and possibly before, if you feel bold, you want to understand:
What is their vision for their career? What do they aspire to? Why?
Their career trajectory:
Did they jump around a lot? Did they stay and get promotions?
What types of roles have they held - are these areas of interest for you?
Who have they learned from? Who has been their mentor?
How do they think about performance:
What factors matter most to them?
How do they handle underperformance?
How do they handle high performers?
How do they give feedback? Are their people ever surprised?
What’s the promotion history of their current team?
Just as your hiring manager is doing reference checks on you, you should be doing reference checks on your potential new manager
Check for LinkedIn recommendations or comments on their posts.
Find common connections and ask for other mutual connections.
Ask to talk to their other direct reports.
Connect with alumni of their department.
Here are some of helpful questions to ask:
How do they handle conflict? With themselves, within the team, with other departments?
How do they give feedback? Do they address it early? Are they clear? Do they give you space to process and respond?
Do they gravitate towards team members with certain characteristics: e.g. great communication skills, ability to navigate numbers, or more introverted?
What is their track record of performance within the organization?
What is their track record of developing leaders? Where do people who report to them go on to do?
3. Don’t give up if they don’t make a great first impression.
If you get to the company and find out your boss is not as strong as you thought, start to look around for other strong leaders.
Before you do — try to do a double check
See if your boss is open to feedback. Test the waters with something as simple as “Would you be open to talking about how we work together?” Use that conversation as a chance to dive deeper into what they’re looking for in a direct report and what you’re looking for in a boss.
Talk to other direct reports.
Talk to other leaders who are peers of your boss — handle these carefully, but they can be the source of excellent intel.
Interviews are notoriously bad ways to get the intel you need, but once you’re on the job, it’s hard to hide the truth.
If you’re not seeing indications that they are open to talking or improving or if you’re finding new evidence points that they aren’t going to be a good boss, then it’s OK to move on.
Pivoting is not a sign that you failed. It’s a sign that you are willing to learn and adapt.
4. Build a pipeline of potential great bosses by developing your network.
For those of you who know me, you’ll know that I believe it’s always a good time to network.
In fact, when you’re happily ensconced in a job you like, that’s the exact moment you should be finding a pathway to your next role.
It’s far better to connect with people when you are happy, fulfilled, and excited about your day-to-day than when you are feeling down.
I’m not saying you can’t have fantastic conversations when you are unhappy, but it will require more emotional labor, and you might find it hard to build momentum.
Always be on the lookout for great boss potential. Some great ways to do this:
Talk to your friends. If they have a great boss or hear of one in their organization, ask for an introduction or try to find a common connection
Read and follow thought leaders. Social media and press are great ways to find leaders who are being lauded for their results and their approach. There is a bit of marketing here, but by and large, the jerks aren’t the ones being acknowledged, and even if they are, a little digging around them will surface that take.
Join memberships and associations. Your alumni network, industry associations, or other membership groups will often have speaker events, networking sessions and conferences, which can be a great way to get exposed to people who you might want to seek out as a boss in the future.
5. Have a great boss? It’s time to cultivate your relationship.
You chose them for their values and their track record. But you might not know how they work and what really makes them tick.
You also haven’t been in the trenches with them, and until you do, you won’t know how your joint chemistry will react to surprises, setbacks, and stresses.
You have an opportunity to start not just on the right foot, but in a thoughtful manner, where you are building trust up-front by talking about the hard subjects before they become awkward.
Similar to my post about The 10 Uncomfortable Topics You Should Discuss with Every New Employee and about writing your Operating Manual, consider initiating a conversation or series of conversations with your boss to discuss some of these topics.
Here’s a simple message template you could use to set it up:
Hi [boss’s name],
I’m so excited to be part of the team. We had some great discussions in our interview process [and as part of onboarding], and if you’re up for it, I’d love to dive a bit deeper with you.
I’ve found that the most productive working relationships are built not just through the work but by aligning on key principles and talking about gnarly subjects like:
What is your vision for success for yourself, your team, the company?
When has someone missed the mark? What do you wish they did differently? How did you address it with them?
What keeps you up at night about my role or function?
What keeps you up at night about the company’s goals or progress?
If I were to really knock it out of the park, what would that look like?
If I have feedback for you, how would you like it shared?
If I or someone on my team disagrees with you or someone else on our leadership team, how have you seen it handled well? Poorly?
We don’t have to go over all of these at once, but I wanted to introduce the idea of aligning on these so that we know in advance how we can best navigate difficult situations in the future.
Happy to set up time at your convenience!
The idea isn’t to boil the ocean. But you also don’t want to avoid the topics that feel the highest risk.
The best time to dive into the hard stuff is at the beginning of the working relationship, when the slate is clean and when neither of you has baggage with each other.
Jump on the opportunity to get into the hard stuff early.
6. Don’t be afraid to move on from a great boss to find another one.
Staying with a great boss is very appealing, but their career goals may not align with yours. Sometimes, it’s as simple as capping your ability to grow because they exist — structurally. This happens when they occupy the only seat above your seat.
But sometimes it’s more nuanced.
Perhaps they are nearing retirement and losing steam whereas you are ramping up or at least wanting to maintain your trajectory.
Another example is if they are fully entrenched in a function or industry while you want to change to another.
Or perhaps they are focused on an area where you don’t have expertise or interest. They are being a great boss, respectful, present, but they aren’t focused on your functional area. They are focused on another area of the business because that’s what the business strategy requires.
This isn’t an us vs. them issue. This is a signal for you to assess if you should move on and find a role or an organization where you are the focus.
Instead of staying the course simply because you love your boss, you should consider moving on. If they are as wonderful as you believe them to be, they will be supportive of your decision and this will be an opportunity to plan the move with their help.
Key Takeaways
Finding a great boss is one of the most important and effective ways to accelerate your career.
Here are some steps to help you find the right ones for your journey:
Understand what makes for a great boss. Define the attributes clearly.
Gather intel about any potential new bosses during your interview process just as your new boss will gather intel about you
Use your onboarding process to dig more deeply into how your new boss operates and makes decisions. This is an excellent time to navigate tough subjects because it should feel less risky.
Leave a boss where you are seeing warning signals or signs that they aren’t willing to improve
Don’t be afraid to move on from a great boss if your goals or focus areas no longer align.
Because in the end, who you work for will shape who you become. If you’re making a career move this year, choose the person — not the job. Your future you will thank you.
I’d love to learn from you: What are some of the key ways a great boss has helped your career?
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May you lead without limits,
P.S.
I’m piloting a new coaching model this fall — unlimited asynchronous coaching (yup, really). Only 5 slots for leaders who want a more flexible coaching model.
DM me or book a 15-min strategy session to learn more.