(I’m vocal in my support of the work First Round Capital has done to help the entire entrepreneurial ecosystem and the First Round Review is a big part of that. When they asked me for thoughts about what candidates should be asking in their interviews, I sent the below; the finished article, with tips from Aubrey Blanche, Adam Grant, and others, is a good read with over 40 questions.)
Here’s the thing about candidate questions: I always try to ask myself “Would I change my decision about working here based on the answer?” If you wouldn’t, then there is no point in asking the question. So focus on dealbreakers: what would make you walk away?
One way to do that? Look at what has made others walk away; Glassdoor is great for this. One of the truths of any situation is that absent different inputs, you can expect the same outputs. So talking about why others left can help you understand the inputs and outputs involved in what might make you leave.
- If you’re interviewing at Coinbase, the question might be “Are you willing to say the words “Black Lives Matter”? Is your boss?”
- If you’re interviewing at Toast, it might be “Can you comment on your labor practice violations?”
- If you’re interviewing at Away, it might be “Why did your VP of People and Culture resign as soon as your CEO returned?”
You may not choose to walk away from those companies as others did. But if you can understand why they did, you can make a more informed decision.
You could do the same thing based on issues you feel strongly about. I tend to ask about how they approach compensation and particularly compensation fairness, since it is a dealbreaker for me and I didn’t ask that often enough early in my career. I also focus on factual questions that don’t have to do with how persuasive they are: what is the title of the most senior underrepresented person at the company?
Side Note: Many of the answers in the article are rooted in privilege but here’s the reality: most job seekers don’t feel like they’re in a position to say no to an offer, especially in this climate. I am often reminded of Shakespear’s line from Romeo and Juliet: “My poverty, not my will, consents.” But even if you’re making a decision based on your poverty, it is important to understand the will, because there will come a time when your poverty is not so strong and you want to remember your options.