- What’s the biggest mistake that you made in the last six months? (Covering their asses, citing minor infraction, laughing at the question, saying they have not thought about it: bad; a sincere admission of a really bad call that sounds like something that will inform their management style: forwarning; either way: they’ll talk about the topic that they care about: financing, recruiting, growth, clients, etc.)
- What’s the biggest mistake that you will in the next six months? Why is it OK for you to expect that from happening? (Same as before, harder to answer; we can learn a lot from others but for some things, no one was here, and this is how we are going to make it OK if we have to: better. Same, will cover the topic that they worry the most about)
- What’s the most important thing that you won’t be able to make if I say no right now? Keep in mind, you have other candidates in the pipe, and I hope that they are good too.
- What’s the biggest problem for people in [your team, or another one that you interviewed with]? (If their answer does not match what you’ve heard from that team: bad; if it does, preferably with one level of abstraction above and a fix.)
Call customer service, and ask them how they feel about the company, preferably before your last interview. “Overworked” is good, “excited” is great. “I’m not sure why I’m here” or “There’s a list of 74 problems that I have, I wanted to raise to the CEO…” good material for your interview. “Not sure, but if you know, tell me: I am the CEO. Talk to yo on Thursday.”: presumably good.
Ask to talk to a client if it’s B2B. They might refuse: “Why?” is a good question then.
I like to ask the investor but that’s because I always go for the same investor… I know, that’s lame. I don’t ask for a name, I just mention one (other) company and ask if they are more, and then respond asking if they could rank them. Depending on the investor, I know that means technical maturity, or business potential, or management. It’s not for everyone, but it helps. You can also ask competing investor and they might let you know why they didn’t invest. Not sure about the ethics of that one though.