Who Has Permission to Tell You You’re Wrong?
Most CEOs don’t make bad decisions because they lack intelligence.
They make bad decisions because leadership can be isolating.
At first, the signs are subtle.
You stop asking for advice because you think you should know the answer.
You stop sharing concerns because you don’t want to create uncertainty.
You stop testing your thinking because fewer people are willing to challenge it.
And that’s when mistakes become expensive.
Not because you’re incapable, because leadership creates blind spots.
The longer you’re in the same business, the harder it becomes to see what others can often spot immediately.
I’ve learned that the best leaders don’t have all the answers. They simply create environments where their thinking gets challenged.
They surround themselves with people who ask difficult questions.
People who aren’t impressed by the title.
People who aren’t afraid to disagree.
People who care more about helping them make the right decision than making them feel comfortable.
In my own journey as a founder, some of the most important decisions I ever made came after someone challenged an assumption I didn’t even realize I was making.
Not because they were smarter than me, but they could see what I couldn’t.
That’s one of the reasons I spent eight years in a CEO peer group: for perspective.
Not for networking, not for referrals, but for unbiased feedback.
Every CEO has blind spots.
The question isn’t whether you have them, but whether you’ve built a system to uncover them before they become costly.
One of the simplest questions I ask founders is this:
Who has permission to tell you you’re wrong?
If that answer takes more than a few seconds, it may be worth thinking about.
The best CEOs I know aren’t the ones with all the answers.
They’re the ones who continually put themselves in rooms where they can learn, be challenged, and see around corners.
That’s true leadership.
-Steven