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I normally write these the Friday before they post. This one came together a little quicker than planned because my dog (appropriately named Zen) literally broke a downstairs window. Cue three and a half hours of cleanup and DIY “window repair.”
So if you’ve got a clever metaphor to turn that into a staffing lesson, reply back and let me know. It probably would’ve been a much more entertaining post than this one.
Why people really leave
Most people don’t quit companies because they hate the work.
They quit because they’ve outgrown their boss.
1. You’re bringing new ideas, and they keep shutting them down.
At first, you thought maybe the timing was off. But after the third or fourth time, you realize: they’re not listening. They’re protecting the status quo, even when you’ve spotted a better way forward.
2. You’re solving problems they don’t even notice.
You’re putting out fires before they start, smoothing over client issues, building systems on the fly…and they’re barely aware of it. What feels like leadership to you looks invisible to them.
3. You’re ready to stretch, but they’d rather keep you “in your lane.”
You’ve mastered your role, and you’re itching to take on more. But instead of opening the door, they double-bolt it. Your curiosity feels like a threat, not an asset.
4. Feedback has turned into micromanagement instead of mentorship.
There’s a difference between guidance and control. Mentorship makes you sharper. Micromanagement makes you smaller. And when every detail is second-guessed, growth gets strangled.
5. The ceiling feels like it’s pressing down, not lifting you up.
The role that once felt expansive now feels suffocating. Every new skill you pick up just bangs against the ceiling above you.
6. You’ve suddenly become a threat.
Instead of being encouraged to grow, you feel the unspoken pressure to shrink. To survive, you start making yourself smaller than you really are.
7. Your wins don’t get celebrated anymore.
What once earned recognition is now brushed off as “expected.” Progress feels invisible. And when your effort isn’t seen, it’s only a matter of time before your motivation fades too.
8. You’re bored out of your mind.
The meetings, the projects, even the problems…they all blur together. You’re not challenged anymore, and worse, you stop caring. Boredom isn’t laziness. It’s a signal that your growth has stalled.
When you’ve hit this point, the choice is simple: stay small, or step out.
The nuance
Here’s what I want to be clear about: outgrowing your boss doesn’t automatically mean they’re a bad person, a terrible leader, or that they don’t care about you.
Early in my career, I reported to someone in operations who had never recruited before. Great intentions. But there was a natural disconnect; I needed mentorship in a craft they hadn’t done themselves.
Later, I had a manager who genuinely valued me, but didn’t want me stepping outside the role I was hired into. The result? I left, and Rogue was born.
You can respect someone, appreciate what they’ve given you, and still recognize that you’ve outgrown what they can offer.
A recent candidate story
I recently spoke with a candidate who had been let go after a manager change. Their new boss came in highly controlling, micromanaging every detail. They got caught up in it and ultimately lost their role.
It hit me: if I had been paired with a manager like that, I wouldn’t have lasted either.
The truth is, management style fit matters as much as job duties. Yet when you’re interviewing, most people are so focused on getting the offer that they forget to ask, What’s it actually like to work for this person?
Here’s my advice:
Be honest with yourself. If you don’t thrive under micromanagers, say so.
Ask directly about management style in the interview.
Don’t settle for “I need the job.” You need the right job.
It’s the same reason I always ask hiring managers in intake calls:
What are your quirks as a leader?
What kind of person thrives under you?
Who tends to struggle?
Those conversations separate a short-term offer from a long-term fit.
If you’re the boss, what to do instead:
Growth doesn’t have to mean losing your best people. But it does require intention. Most of that work happens in your 1:1s.
Here are a few ways to shift them from status updates into growth conversations:
1. Give them stretch work before they ask for it.
Ask: “What’s one thing outside your current role you’d like to try?”
Small projects and test runs show you trust them, and give them room to grow.
2. Ask “what’s next for you?” regularly.
Not just in performance reviews. In everyday conversations.
Ask: “Six months from now, what do you want to be better at?”
3. Ask the questions you’re a little afraid to hear the answers to.
Try: “What’s one thing I do that makes your job harder?” or “Where do you wish I’d get out of your way?”
The answer might sting. But if your team can’t tell you the truth, they’ll eventually vote with their feet.
Pro tip: Don’t defend yourself. Just listen, thank them, and act.
4. Move from gatekeeper to sponsor.
Don’t just control opportunities. Open doors.
Ask: “Who do you need more exposure to here, and how can I help make that happen?”
5. Accept that sometimes, their next step will be outside your team.
Ask: “If you could design your dream next role, what would it look like?”
And then support them, even if it means sending them off stronger.
The parallel
For employees: don’t be afraid to ask about management style in interviews. It feels risky, but better to find out you won’t thrive under a micromanager before you accept the offer than six months into the job.
For leaders: don’t be afraid to ask for feedback on your own style in 1:1s. It feels uncomfortable, but better to know where you’re blocking growth than to lose your best people because no one felt safe enough to tell you.
The takeaway
If you’re the employee: outgrowing your boss isn’t betrayal. It’s growth.
If you’re the boss: don’t be the ceiling. Be the launchpad.
See you next Monday,
Robin
#gorogue
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