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by daylightyotei 2803 days ago
> If you're thinking about joining a startup, how do you tell if the founders are like Larry and Sergey or if they're an Elizabeth Holmes? Right, that's the worst combination: smart and full of st. I think you have to interview them a little bit. Ask hard questions and see if they give direct, insightful answers, or if they're evasive and dismissive.

What are some examples of "hard questions" that we can ask?

3 comments

I think you can determine if they are evasive and dismissive without needing hard questions. Ask about their history. Ask them about their leadership style. Ask them how they resolve conflict in their organization.

If they have good answers to those questions that don't feel like canned responses, then go dig deeper. Ask their employees about their leadership style - do the answers match? Does their resume and google-stalking match their story of their history? Ask the team about organizational conflict resolution. You should get similar responses.

Also, think about whether they talked to you like a leader. I've had interviews when I really enjoyed talking to the potential boss, and it felt friendly, and those turned out to be sub-optimal leaders. But the good leaders I've worked for interviewed in a way where I was comfortable, but challenged by the questions, and they stayed focused. They didn't chit-chat or make friends (at least not beyond just a few quick minutes as we got started), they drove towards getting the answers they needed to see if I was right for the job, and they gave me opportunities to ask questions back.

Every startup's "founding story" is in some part fictional, so the easiest thing is to just find something that doesn't make sense in their pitch, and ask about it, directly.

In the startup world, bullshitters are pretty much the norm, so finding bullshit isn't difficult. What's difficult is ignoring the hype bubble and social pressures that come with challenging people who are well-funded (and of course, sometimes you're wrong, which is part of what makes it hard).

Even if you're wrong, though, a non-bullshit answer to a pointed question will address the question. Most people, however, will just say words that dance around your question, clarifying nothing. In that case, you have to have the guts to keep asking followup questions, even if it makes the bullshitter uncomfortable.

When I think back over my history, I've always had a pretty good idea about the bullshit level of various employers simply by asking simple things like "how do you make money?" Good entrepreneurs will simply tell you (even if the answer is "we don't, yet"). Bad entrepreneurs will dress it up and try to hide their answer in word salad. Avoid these people.

How are they going to get money