Tell me about a time you fought… and lost.
(my favorite interview question)
Pomello is currently hiring so asking great questions is top of mind. This is why I like “Tell me about a time you fought hard and lost.” First it fills a gap in our current interview process, and second it allows me to evaluate more than one thing about a candidate.
As you may know Pomello focuses on helping teams understand their culture and identify candidates that share the same workplace values and priorities. We like to think of this as one of the major missing components in many evaluation processes. But someone asked me a great question recently.
“What about emotional maturity?”
As we’ve been interviewing candidates for our senior engineering role, we’ve been looking for someone who is 1)technically skilled at the level we need and 2) aligned with our values. This question highlighted a major gap in our analysis, and here’s why.
Pomello is an early-stage, seed-funded company. We are a small tight-knit team, that operates under conditions of extreme uncertainty. Anyone joining our team is likely to participate in frequent discussions (read: disagreements) about how to solve our most pressing problems. Disagreement on an early-stage team isn’t a problem, and it can actually be a huge benefit. But that benefit can only be realized if disagreement doesn’t result in the erosion of trust.
Having strong agreement around team values mitigates some of this risk, but it also takes emotional maturity to overcome disagreements on a regular basis. An emotionally mature person recognizes that they might not be right all the time. They recognize that there are many battles to fight, some will be won and some will be lost. And finally they realize that losing a battle at work doesn’t take away from their position at work; in fact, it elevates the company as a whole to have high integrity disagreements.
This question is open-ended, and it actually isn’t even a question. It’s just a request for someone to tell me a story and give me whatever context they want. As a result, I can derive a lot of insight into how a person’s rational and emotional mind works. This is how I break down a candidate’s answer to this request.
- I ask myself if they are able to separate the rational from the emotional e.g. can they articulate the rationale of the winning side without throwing it under the bus irrationally.
- I ask myself (and sometimes the candidate directly) how they feel about what happened. I am looking for them to acknowledge feelings of disappointment, defensiveness, even hurt. It’s important for people to be able to express their emotions.
- I ask myself whether I think the candidate has put distance on the event or whether they are harboring resentment and bitterness. I want to know that someone is capable of moving past a particular event.
So with that in mind let me ask you a question.
“What’s your favorite interview question, and why?”
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