The Most Important Interview Question

My favorite interview of all time happened at an early-stage start-up. The last interviewer of the day sat down and asked me “Do you have any questions?”

I thought he was just being nice and giving me time to get my questions in. But after I asked my question, and he answered, he continued with “any others?” and then “any more?” and “do you have another?”

I asked him at one point, “Do you have questions for me?” but he said “I’m good. You’ve been answering questions all day; I’ll just check in with my team.”

So I asked him questions for an hour and a half, and he patiently answered each, then requested another.

Finally, exhausted and out of questions but unwilling to relinquish this awesome person who was willing to tell me anything, I finally asked “what question should I be asking you that I haven’t?”

That was magic.

The reality is that no matter how much homework I’d done, I don’t know the company and what it’s like to work there as well as someone who does. When I asked “what question should I have asked you?” he told me very important things about the culture and the work-life balance that allowed me to make good choices about the fit. And fit is everything; if you go to a company where fit is bad, you will fail.

Since then, I make it the question I always ask. If I’m short on time because the interview is drawing to a close, I’ll make it the only question I ask.

Sometimes when I ask, “what question should I ask you?” the interviewer can’t think of anything, which is telling in its own way. But often the interviewer can’t help but think of the hardest challenges the company faces, or that I would face while trying to succeed. And that is exactly what I need to know to make a good decision.

I had taken another lesson from that wise interviewer, and usually start my interviewing with “Do you have any questions for me?” This allows the person on the interview to get comfortable, gain control and take an active role in the interview. As well, questions often tell me more than answers. But I never asked “what question should I have asked you”… I thought, surely they are so prepared it won’t help. I was wrong.

One day, I was interviewing a prospective employee that I was having trouble getting a handle on. Frustrated, I asked him, “what question should I ask you?” And once again it changed the nature of the conversation. It allowed the person who knew the most to come up with the best questions.

Now, some interviewees do get flustered, because something negative will pop in their mind and they’re trying not to share it. I think we all have something we wish we did better, so I don’t take it negatively at all. I just sit quietly, smiling and waiting while they order their thoughts. But most folks have this one amazing thing they did they are just dying for me to ask about. It’s a chance for them to tell me a story that doesn’t easily fit into a portfolio or resume, and it’s usually a very interesting and very telling one.

Interviewing is an archetypal example of “you don’t know what you don’t know.” Asking “what question should I ask you?” gets your interview partner to help you ask the right questions.


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    dan t.

    Argh! I’m arghing because this is a great post, and I wish I’d read it before my interview today.

    And this is also a magic question for journalist, too. I knew that, and totally forgot.

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