I carry a small note card with me.
It’s got four questions on it. I’ve been carrying it for years.
Not because I read it every day — I don’t. But because there are days I’m certain I’m right, and those are the days I need it most.
This week, 2,000+ entrepreneurs are flying in to the EOS Conference to sit in rooms and take notes. To listen instead of lead. To be students again. (FYI – I’ll be there. Love to say hi!)
If you’re one of them, you’re already doing something most founders never do.
Most founders spend 365 days a year being the smartest person in every room they walk into.
That’s not arrogance. It’s math.
You built the company. You understand the numbers, the history, the strategy, the customers, the team, the competition — at a depth nobody else has the context to match.
But here’s what that depth quietly costs you:
You stop asking.
You stop being surprised.
You start confusing “I have the context” with “I have the answer.”
And at some point, you become someone who’s always right… in a room full of people who’ve stopped telling you when you’re wrong.
That’s the most dangerous phase of a founder’s career.
The Rarest Trait
In VISIONARY, I made a claim I stand by:
Intellectual humility might be the rarest trait of all — and it’s shared by every truly great Visionary I’ve ever worked with.
Not vision. Not discipline. Not work ethic.
Humility about what you know.
Which is strange, because Visionaries are wired to believe. To see possibilities others can’t. To bet on a future that doesn’t exist yet. That’s the gift.
And the same wiring that lets you see what others can’t is also what makes it easy to stop listening.
The great ones catch themselves doing it. They stay curious. They ask questions instead of making declarations. They hold their beliefs loosely enough to let new information actually move them.
The rest calcify.
The Four Questions
Author Warren Berger laid out a set of four questions to assess your own intellectual humility. I came across them through Daniel Pink. They resonated so strongly with me that I wrote them down, stuck them on a note card, and have been carrying them ever since.
Here they are:
1. Do I think more like a soldier or a scout?
Soldiers defend positions. Scouts explore new territory. Both have their moments. But founders who’ve stopped scouting start losing the wars they don’t even know they’re fighting.
2. Would I rather be right, or would I rather understand?
Most of the time, you have to choose. You can win the argument, or you can learn something. Rarely both.
3. Do I actively seek out opposing views?
Not “tolerate them when they show up.” Actively seek them. Put them on the calendar. Hire people who disagree with you. Read the articles that make you roll your eyes.
4. Do I enjoy the pleasant surprise of discovering I’m mistaken?
This is the tell. If you notice a little lift when you’re proven wrong, like it was an unexpected gift, you’ve got the mindset. If being wrong feels like losing, you don’t.
Answer them honestly. One of the four will land harder than the others. That’s the one worth sitting with.
The Missing Piece
Here’s what very few people talk about: You can’t practice intellectual humility in a vacuum.
The four questions are a mindset. But mindsets need input. And the input has to come from people who are both qualified AND allowed to tell you you’re wrong.
For many founders, that list is shorter than they realize.
Your direct reports can’t really do it… they work for you.
Your spouse can do it on personal things, but rarely on business strategy.
Your friends can do it on life stuff, but most don’t understand your business.
Your customers will tell you when you’re wrong, but usually only after you’ve already lost them.
This is why I teach the Shield Wall: a small set of vital people posted around the Visionary to help keep you honest with yourself. A peer group of founders who’ve been where you’re going. A coach who isn’t afraid of you. A mentor or two who earned the right to push back. Family members who know you outside the business. Your Integrator, if you’ve explicitly given them permission.
Without that wall, the four questions become rhetorical. You’re asking yourself things you have no evidence to answer.
The founders who stay intellectually humble over decades aren’t the ones who try harder. They’re the ones who’ve built the structure that makes humility unavoidable.
They’re surrounded by people who love them enough to tell them the truth.
Your Gut Check
Three questions worth sitting with:
- When was the last time someone told you you were flat wrong about something that mattered? If you have to think for more than 30 seconds, your Shield Wall is thinner than you think.
- Of Berger’s four questions, which one made you flinch? There’s one. There always is. That’s your opportunity.
- If you’re heading to the EOS Conference this week, are you going as a student, or as someone hoping to be recognized?
The conference is one of the rare moments in a year where founders get to practice being wrong in public. Don’t waste it.
Go with the mindset of the scout. Not the soldier.
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