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Brian Halligan: preference

15 Feb 2026 Lenny's Podcast Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

“Before he's got a C-level interview, CFO, chief product officer, whatever, he has some sign an NDA, and sends them the last board deck, or the board memo, or some important doc, and he schedules a half hour interview with them, and he just has a chat about the decks. And if they're just very complimentary, and it's so great, and you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person.”

— Brian Halligan

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Speaker
Brian Halligan
Attribution
Verified speaker
Claim type
preference
Recorded
15 Feb 2026
Publisher
Lenny's Podcast

Transcript context

…What do you do when you coach someone on that? When you're like, okay, you think you're amazing at interviewing, you think you know who's going to work out, what advice do you give them to help them develop that skill? I think even me, I've been doing this for 150 years, I still think I overrate my ability to interview someone, and really know if they're a good fit. I give a couple pieces of advice. Parker Conrad has a good hack that I liked. Before he's got a C-level interview, CFO, chief product officer, whatever, he has some sign an NDA, and sends them the last board deck, or the board memo, or some important doc, and he schedules a half hour interview with them, and he just has a chat about the decks. And if they're just very complimentary, and it's so great, and you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person. And I thought that was a pretty good hack to get inside someone's head and how they think and how they'll interact with you. Getting on a whiteboard and working through a problem I think is always a good thing. I think the standard interview of walking through your background, I don't think is all that valuable. And I coach people to do blind references, find someone you know that work with them... VCs are good at this by the way. And I get a lot of these, and you can tell some of them are like, we've already decided we're checking the box, versus they're asking me hard questions about this person. And one of my favorite questions people ask is, would you enthusiastically rehire this person for that role? Which I think is a really good question. On a scale of one to 10, how likely is it that you'll try to rehire this person back from me down the road? I think those types of questions are good, so not mailing an in on those blind references I think is really good. My other piece of advice, and no one listens to me on this, is hire slow and fire fast. People hire fast and fire slow. If I had to guess, Lenny, with 18 months after you hire a C-level exec, at least 50% of the time they're gone. High mortality rate on them, it's harder than people think. And so, what you're saying here is there's only so much you can actually do to increase those odds.…

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