The Leadership Skill That Gets Harder, Not Easier, With Seniority

There’s a leadership skill that gets harder, not easier, the more senior you become.

Almost no one warns you about it. It’s not in the leadership books. It doesn’t show up in the 360 reviews.

But in 20+ years of watching senior careers play out, I’ve come to believe it’s the single most important difference between leaders who keep growing past the VP level and the ones who plateau there.

The skill is this: receiving feedback that nobody is brave enough to give you anymore.

When you’re early in your career, feedback is abundant. Your boss tells you. Your peers tell you. Your direct reports tell you informally. Everyone has an opinion about how you’re doing because the stakes are low and the power differential is small.

Then you get senior. And it stops.

Your boss tells you less, because the people above you are also more political. Your peers tell you less, because they’re either competing with you or working for you. Your direct reports tell you almost nothing real, because the consequences for them of being wrong about you are now significant.

So you stop receiving feedback. Which would be fine if you’d stopped having blind spots. You haven’t. Your blind spots have just become more expensive.

Here’s the work, if you’re at the senior level and noticing this:

1. Build at least one peer relationship where the contract is honesty.
Another senior leader, outside your reporting chain, ideally in another company, where the explicit agreement is that you’ll tell each other the truth. Not feedback in the abstract — the actual observation, when one of you sees it. These relationships are rare. They are the single most useful infrastructure for senior career longevity.

2. Hire a coach who is unafraid of you.
There are coaches whose role is to affirm. There are coaches whose role is to challenge. At the senior level, you need the second one. Someone who has worked with people at or above your level and is not impressed by your title. If your coach has never made you uncomfortable, you’ve hired the wrong one.

3. Ask your direct reports for one specific thing.
Not “any feedback.” That gets you the answer they think is safe. Ask them, in the next 1:1: “What’s one thing about how I lead this team that you think I might not see?” The specificity gives them something to point at. Then receive the answer cleanly. No defending, no contextualizing, no explaining. Just thank them. 

4. Watch for the leader who never gets pushed back on.
This is the warning sign. When you notice that nobody is challenging your thinking anymore that’s not because you’ve become so right that disagreement is unnecessary. It’s because the room has decided it’s not safe to push back. That’s the moment careers quietly stall. 

If you’re a senior leader reading this and you can’t remember the last time someone said something to you that you didn’t want to hear that’s not because nobody had anything to say. It’s because the room got too quiet.