Three unconventional interview questions

A few ideas to help applicants open up

Hiring is never easy. Attracting qualified candidates is hard enough — then, there are interviews.

An interview is often the only collection of minutes you get with a stranger before signing up to spend, theoretically, several years with them. Depending on the role, this near-blind jump can be a huge risk for the business. So how do you get the most from that initial short meeting?

Different jobs are famous for different kinds of questions. Tech startups might try and stump you with a brain teaser or have you work out a problem on a whiteboard. Traditional office jobs often ask about your strengths and weaknesses, to tell them a story of solving a problem at your last job, and the old “where do you see yourself in five years?”

And almost every interview is going to close by asking the applicant if they have their own questions, which is a good indicator of how interested and/or curious someone is.

At Slack, we look for a lot of things, but we’re especially keen on finding people with lots of empathy for our users, whether the employee is building software as an Android engineer or providing support on our customer experience team. I’ve found it’s not easy to interview for those qualities, but one way is giving candidates an opportunity to open up and talk about themselves and their experiences, which not only highlights how they think through problems and solutions, but also how they think about the world.

Toward that end, I’m sharing a few interview questions I gathered after asking friends for advice. They’re helpful in getting to know strangers beyond their resume in the few short minutes you have together.


What’s a personal opinion you’ve had and changed in the last year?

Tech industry pioneer Anil Dash shared this question, and it’s a good one. This question asks people to explain how they’ve changed their thinking on an issue in the recent past, and asks them to explain why. No two answers are going to be the same but it’s a good indicator of whether or not someone is humble and open to re-examining their beliefs in the face of contrary evidence. It speaks to the mantra of “Strong opinions, weakly held” which is generally a good thing on big teams that must compromise often. About the only bad answer to this question is when someone says the equivalent of “Nothing! I make up my mind and stick to it.”


What’s the best (or worst) piece of advice you’ve gotten?

Fellow writer Donovan X. Ramsey mentioned this one to me. For this question, the answers tell you a lot about how a person can reflect on their past and draw lessons from it worth sharing with others. If someone feels stumped by this, it’s often easier for people to recall failures, so flip the question. It might not be a great sign if someone is completely stumped either way, but it’s ok to give them time to reflect and come back to it later in your interview.


Tell me a story about how luck played a role in your life.

This is a question we often ask candidates interviewing at Slack. It gets a bit closer to being directly about empathy. It’s another indication of someone’s humility as they talk about their past and acknowledge when they got a lucky break that gave them a leg up. In some cases, this can potentially open up a conversation about privilege, and whether an applicant recognizes any advantages they may have had in getting to where they are.

I don’t have any quantitative data to back up these questions, but over the past few interviews I felt more informed when it came time to vote on making candidates possible colleagues. Amid your other questions about an applicant’s experience and the job they are applying for, you might try using one of these to broaden the conversation and get to know people a little better.


Matt Haughey’s first time interviewing someone for a job started with “Hi, I’ve never done this before!”

About Slack

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