I’ve been a board member and investor for a long time now, and I’ve developed a simple habit with executive candidates. I try to be one of the last interviews. By that point, the candidate has usually done 8, 10, sometimes more conversations with the founding team.
And I ask one question: “You’ve done 10 interviews now. Tell me what you’ve learned.”
More than 90% of the time, they can’t answer it well.
They can tell me the company is “exciting.” They can repeat back the pitch deck version of the opportunity. They can tell me they liked the CEO and the team. But they can’t tell me the real risks. They can’t tell me the unit economics. They don’t know the burn rate, the retention numbers, or what was in the last board pack. After 10 meetings, they have vibes. Not knowledge.
And that, to me, is a disqualifier.
If You’re Not Curious Enough to Learn the Business in 10 Interviews, How Will You Run It?
This isn’t a trick question. I’m not quizzing them on trivia. I’m looking for evidence that across 10 conversations with the CEO, the co-founder, the team, they were curious enough to dig in. That they asked hard questions. That they pushed past the sell job and tried to actually understand the business they’re about to bet their career on.
The best candidates blow me away. They’ve reverse-engineered the revenue model from the pricing page. They’ve asked about churn in every interview. They’ve talked to customers on their own. They’ve figured out where the org chart has gaps. They come in and basically brief me on the state of the company.
But that’s maybe 1 in 10.
The Training Program Story
Early on at one very fast growing statup, I interviewed a candidate who was everyone was very excited about. He kept talking about wanting a really extensive training program. So I asked: “Do you know what the training program looks like with just eight people at the company?”
He didn’t know. He was hoping it was really extensive.
There was no training program. There were six people. And this person had done 10 interviews without asking a single question that would have surfaced that. Adam got a little mad at me for being so direct about it with the candidate. But we avoided a mishire. That candidate lacked the curiosity to figure out the most basic operational reality of the company he was about to join.
What This Really Filters For
When I tell the CEO what the candidate didn’t learn, it’s usually a lot. Fundamental things about the business, the competitive landscape, the financial position. Stuff that should have come up naturally if the candidate was genuinely curious.
And that’s the filter. Not whether someone has the right resume or the right playbook. It’s whether they’re wired to learn a business from the inside out before they even start.
A VP or CRO who joins a startup without having seen the board pack, without knowing the real retention numbers, without understanding the actual stage of the company… that’s not just a miss on due diligence. It tells you how they’ll operate once they’re in the seat. If they’re not asking hard questions as a candidate, they won’t ask hard questions as an executive.
Slow down. Be the last interview when you can. Ask what they’ve learned. You’ll know in about 90 seconds whether you’re talking to someone who’s genuinely curious about the business, or someone who’s just interviewing well.
