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The personality test many founders ignore explains nearly every mistake they make.
I’ve spent my whole career teaching people skills. My book The Art of People laid out 53 principles for understanding, connecting with, and influencing others, and I’ve written here before about the red flags I look for after hiring more than 1,000 people and the questions I ask before investing in any startup. But here’s the part most founders skip, and it’s the part I put first in the book for a reason: before you can read anyone else, you have to read yourself.
The single best tool I’ve found for that is the Enneagram.
If you haven’t encountered it, the Enneagram is a personality framework that sorts people into nine core types based not on how you behave, but on why — the fears and motivations underneath the behavior. That’s what separates it from the personality tests you took at some corporate offsite and immediately forgot. Myers-Briggs tells you what you do. The Enneagram tells you what you’re afraid of. And in my experience, what you’re afraid of is what’s actually running your company.
Here’s why this matters so much for founders specifically.
Your type explains your hiring blind spots. Founders don’t hire objectively. We hire people who feel comfortable, and “comfortable” usually means “wired like me.” When Carrie and I were building Likeable Media, our best hires were consistently the people least like me — the detail-driven operators who found the holes in my big swings. Once you know your type, you can name the gap you’re unconsciously avoiding and hire for it on purpose instead of by accident.
Your type explains your conflict style. Some types go quiet under stress. Some get controlling. Some get busy — piling on new projects so they never have to sit with the hard conversation. None of these are character flaws; they’re default settings. But a founder who doesn’t know their default setting will burn out their team wondering why every disagreement follows the same script.
Your type explains your co-founder friction. Carrie and I are different Enneagram types, and honestly, that’s the entire reason our partnership worked — and the entire reason it almost didn’t. The same wiring that made us complementary in the org chart made us combustible in the conference room. Understanding our types didn’t end our fights. It changed what the fights were about. Instead of “you always do this,” it became “ah, there’s your type doing its thing” — which sounds small, but it’s the difference between attacking a person and observing a pattern.
So here’s my challenge for you this week, and it costs almost nothing:
First, take the assessment. There are several good ones online; the test itself takes 20 minutes. Read your type’s description of what you look like under stress. If you don’t wince at least once, take it again — you answered as the person you want to be, not the person you are.
Second, have your leadership team take it too. Not so you can put people in boxes — so you have a shared, neutral language for the dynamics that are otherwise invisible. “That’s my type talking” defuses a room faster than any management training I’ve ever paid for.
Third, map your gaps. Look at your top three business problems. I’d bet at least two of them are downstream of your type’s blind spot. Mine always were.
In an age when AI can analyze your metrics, draft your strategy, and write your emails, self-awareness is one of the few advantages left that compounds. Machines are getting smarter about everything except the person in the mirror. That one’s still your job.
Read yourself first. Everyone else gets easier after that.
This post originally appeared at inc.com.
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