My favorite job interview question

I like job interviews.

I participated in a lot of job interviews in 2017. I interviewed extensively before starting at SoundCloud, and then again on my way to my current position at The Wall Street Journal.

Sometimes, interviews are full of fascinating cultural signals. Most times, interviews are full of tired and cliche questions.

For example, “What’s your greatest weakness?” This is the Monopoly of questions: everyone knows the rules, and nobody likes playing. The interviewee is expected to come up with an insightful comment about their own shortcomings, without revealing any of their actual shortcomings. The interviewer is saying nothing about the company’s values — except that the company doesn’t value originality¹.

It’s a lose-lose question.

Prompting introspection is a really powerful interview tactic, but “what’s your greatest weakness” is the worst way to go about it. Instead, try this prompt:

Tell me about a time that you were wrong.

You’ll send strong cultural signals to the applicant. You’ll allows the applicant to pack meaningful personal information into their answer. It’s easy to understand, and works for every level of every position.

What the prompt tells an applicant about the organization

Most interviews waste a lot of time talking about getting things right. “You should come work for us because we get things right.” “You should hire me because I get things right.” “How will you make the company get things right more often?” And so on.

Being right is great, but it’s boring. Being right doesn’t lead to self-reflection or growth. Being right is often misattributed. Being right is expected.

By asking about a time the candidate was wrong, you make an important acknowledgement: being wrong happens. You also show that you value balance, reflection, honesty, candor, and humility.

When you give the prompt, your posture while listening to the answer can communicate a lot. Try to listen actively: you’ll signal your interest in learning from getting it wrong, too.

What the answer tells the interviewer about the candidate

Recognizing that you were wrong is hard. To actually talk to another person about what you got wrong is emotionally challenging. Give the candidate some time with this prompt, and you’ll learn a lot about them.

Some possible scenarios:

• The candidate answers quickly and thoroughly. This might mean that they’ve spent time understanding their experience. They’re comfortable acknowledging where they fell short. Either that, or they read this essay and had time to prepare².
• The candidate works through their answer slowly, with some effort. Being open to introspection with a stranger is a positive trait. How the candidate works through the answer says a lot: they might talk candidly, or might be sheepish. They may collect a few related experiences, or go deep on one. This process is a good preview of how they’ll handle communication challenges in their role.
• The candidate doesn’t have an answer right away. Some people expend all their mental energy simply showing up to a job interview. It’s a stressful experience, and they might not have the space for emotional candor. Encourage them to follow up later in an email. Depending on the team and the role, face-to-face candor might never be a factor.
• The candidate doesn’t get things wrong. Don’t hire this person.

The content of the candidate’s answer signals a lot, too. The contrast between the risk involved (were there negative repercussions?) and the candidate’s certainty about their decision at the time (were they surprised when they were wrong?) is particuarly interesting.

• Low risk, low certainty: “I picked the wrong socks for this interview” is a good joke, and hopefully it’s followed by a better answer.
• Low risk, high certainty: “I thought the CEO would like an update every day.” It’s good to acknowledge that being certain and being right are separate things, but low-risk mistakes are common and easily brushed off.
• High risk, low certainty: “We were on deadline and I decided to cut corners.” Situational pressures are going to exist in every role in every organization. Understanding how a candidate will respond to them is valuable.
• High risk, high certainty: “I decided to ship because I thought we were ready.” This is my favorite kind of answer. You’ll never hire someone who doesn’t make mistakes. Try to hire someone who will take responsibility for mistakes, no matter how high the stakes are.

How to use this prompt

I follow this prompt with “ok, now tell me about a time you were right.” This gives the candidate time to recover after the emotional effort required for good introspection. The response also tends to be much more genuine and less self-aggrandizing when framed with the previous prompt.

Similarly, I like to put this prompt earlier in the interview. The conversation that follows tends to be more candid, and more natural. “Tell me about a time you were wrong” defuses a great deal of the tension of the typical job interview. Instead of feeling pressure to convey merit through past accomplishments (a relatively low-value indicator of future performance), the candidate has the opportunity to demonstrate strong communication skills (a high-value indicator of future performance).

Acknowledgements

Thanks to Josh Petersel for providing feedback and edits on an earlier version of this essay.