Eight Sleep founder's five favorite interview questions

Eight Sleep's founder uses five questions to evaluate candidates across their entire work history: how they found each job, their biggest achievement, their lowest point, what their manager would say about them, and why they left. He covers five jobs in 20 to 25 minutes and spots red flags fast.
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I run all the interviews with the same playbook. And that helps me because now I have seen thousands of candidates with the same playbook, the same questions, right? And so I can identify certain red flags faster. What are the playbooks? I go through each of your previous jobs and I ask you five questions. How did you find the job and what did they hire you for? And so that helps you, because in how you fund the job, if they had five, six jobs, you want to see if they were recommended by anyone or the previous managers. That is a great sign. If it never happens, it's not a red flag, but it's not a positive sign. Second biggest achievement. Biggest achievement. Seems a stupid question, but it's one of the greatest questions. Because if you start talking to me about, oh, I bonded with my people or my teammates, I assume that you bond with the other teammates. I'm talking about what has been the biggest achievement, your biggest contribution, you, not your team. And the best people come back with data. I improved the CVR of the website from 8% to 9.2% by doing a, B and C. That is a great thing. If they are fluffy, still struggling. Third question is, what has been the lowest point? And this is another great one, because a lot of people, they start complaining and you see what they complain about, oh, my manager, they never gave me the right task and this and that, or they didn't give me enough freedom to operate, blah, blah, blah. Then you ask, who was your manager and what are they going to say about you in the next reference check? But you want to say in the reference check, because they can lie because they know that you will do the reference check. And so there you immediately see certain people becoming rigid. You know, I mean, we had a good relationship, but it was not really perfect. My manager and the last one, why did you leave? And there is a soft way to know, did they push you out with a reef? And when you start doing for five jobs, five, six jobs, you start seeing patterns. And so when I go back to you as an executive is not Matteo's opinion is I come back with a list because I take notes and I saw X red flags and at that point, they trust me. How long does that take? This is another great question. With the great people, in 20, 25 minutes, I can go through five jobs there fast. There are some people where you go through two jobs in 30 minutes. And that is another red flag, because I have it sometimes half an hour. And they're like, and then I went to Stanford and you're like, oh, no, I totally agree.
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