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What’s the Best Interview Question?

by Jamie Flinchbaugh on 02-11-25

What’s the best interview question you’ve ever received or given?

Your list of bad interview questions is likely much longer than your list of great interview questions. I’ve heard some amazing horror stories about interviews derailed by terrible questions!  But still, there seems to be more advice available about responding to bad interview questions than how to conduct good interviews.

While listening to an interview during last year’s NACD Summit, I heard a fantastic question. It was shared by Adam Bryant who wrote a column for the NY Times called The Corner Office, and the interview subject was Corey Thomas, CEO of Rapid7. Here’s what he said:

I also ask people what their triggers are. If an executive can’t answer what their triggers are, that’s a nonstarter. We all have them, and if you’re not aware of them, that probably means you lack maturity around them. If they’re aware of their triggers, I ask them how they manage them.

 This question is more about the impact of Self-Awareness and Self-Regulation than it is about the specifics of the triggers themselves.

While questions about skills and strengths are important, they’re not as vital to performance (especially for leaders) as the traits of self-awareness and self-regulation. Skills are often very short-term in nature and sometimes only relate to a specific gap a candidate was trying to close. There are skills that are not short-term in nature such as problem solving, decision making, and strategic thinking. However, one’s mastery of these skills will rarely be enough to disqualify them or put them over the top.

Self-awareness is vital in many ways. First, it’s an essential precursor to continuous improvement. Second, it puts one in the best position for success. For example, I know some of my gaps require me to have other people around me and this is one of the reasons I always had co-founders for startups rather than going solo. Self-awareness also prevents us from overreaching or becoming overconfident. Many of the most epic failures in military history (and business history for that matter) come down to a root cause of overconfidence stemming from a lack of self-awareness.

Lack of self-regulation creates a gap between triggers and behavior. There’s nothing wrong with being mad when someone cuts you off in traffic, but allowing (or not allowing) that act to make you behave contrary to your best interest is where self-regulation comes in.

Why does an employer care about this? In the extreme, they want to know if you’ll implode, or explode, requiring intervention. We’ve all seen people “lose it” and start to act irrationally, leading to their removal. But that’s not the main reason an employer should pay close attention to a candidate’s self-awareness and self-regulation.

The key is this: how many of an applicant’s best days will I get if I hire them? If they’re triggered and not self-regulating, I won’t get their best performance, greatest output, or clearest thinking that day. How many days will that be the case? Productivity goes way beyond a simple sum of hours worked, but is very dependent upon the performance during those hours.

Self-regulation is a combination of general approaches and trigger-specific strategies.  In the general approach, I’ve found the most effective mechanism to be the study of Stoicism and the adoption of empathy. Without opening the gigantic can of worms that is an entire philosophy, Stoicism teaches us that when someone does something against you, it
(a) says more about them than it does about you
(b) allowing them to affect your mind and behaviors is self-imposed, not imposed on you. 

For example, Marcus Aurelius wrote “If you are pained by any external thing, it is not this thing that disturbs you, but your own judgment about it. And it is in your power to wipe out this judgment now.”

Empathy, or even rigorous empathy, returning to the example of someone cutting you off, means that you might try to understand someone who is so self-involved that they’re willing to be rude and/or dangerous for minimal gain. Understanding someone, or giving them the benefit of the doubt versus being mad at them isn’t about right or wrong, it’s about whether you choose to have a good day or a bad one. 

I’m not doing a lot of hiring these days, so I don’t know how many times I’ll be able to use Adam’s interview question above, but I hope I get a few chances as I find it incredibly high-leverage and insightful.