I’ve been in rooms with brilliant leaders who hadn’t been challenged in years.
You can feel it. A certain settled quality to their thinking. Confident in ways that have nothing to do with evidence. Surrounded by people who have learned, often through hard experience, that disagreement is not rewarded.
It worries me every time.
I tell my clients the same thing: find someone who is willing to annoy you. Not a provocateur. Not a critic for sport. Someone who respects you enough to say the thing you don’t want to hear, and cares enough about your growth to say it anyway.
The assumptions we’ve never tested don’t feel like assumptions. They feel like facts.
That’s the danger.
ChatGPT will affirm you. Your board will be polite. Your peers will be kind. None of that is what you need when you’re making decisions that will shape the next three years of your business.
What you need is someone who asks the uncomfortable question. Who pushes back on the strategy everyone else has quietly accepted. Who sees the vulnerability you’ve convinced yourself isn’t there.
If you don’t have that person, ask yourself why.
Because the answer to that question is usually the most important work you have in front of you.
The assumptions you’re willing to test are your path forward. The ones you’re not, those are the ones keeping you exactly where you are.
