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I've held positions in several companies where I needed to make hiring decisions. That includes Square (Block), Weebly, and FutureFund, the free fundraising platform for K-12 school groups that I founded. All of those businesses require talent with specialized skills and experience, but you might be surprised at how few questions I ask during interviews.
In fact, after conducting interviews with more than 2000 candidates for different positions over the course of my career, I've learned that there are only two questions that really matter. And if you're listening to the answers, they'll tell you everything you need to know about whether to hire the person giving them.
Here's what they are and why.
Related: The 4 Keys to Asking Better Questions
"What have you been working on?"
This might seem too open-ended, but that's actually the point. You allow people to keep their responses on the rails when you're too specific with your questions. But when you ask a question like this one, their minds go to places you haven't directed them.
Most people — especially in tech — have more than one or two projects on the go at any given moment. Ask what they're working on, and they'll have to narrow down all the potential answers they could give on the spur of the moment to tell you about the one that looms largest in their minds.
In that moment, you'll learn a lot about their real priorities.
But that's not all. The candidates may even surprise themselves. It's not just that they haven't had time to think about what the most diplomatic or people-pleasing answer is — their subconscious priorities may not even align with what they've told themselves is most important to share.
Watch and listen closely after asking this question, and you'll learn more than just what kind of work your potential candidate is most interested in doing. You can also learn how aware they are of their own interests, which can tell you a lot about their future reliability in your workplace.
The second question works in a similar way. But it can teach you even more.
"What do you want to do?"
If you've just finished asking the candidate what they've been working on, this question might seem redundant. You've already formed a picture of their priorities through the last answer they gave, so why are you asking?
Simple: you're listening to see how well their answers match. If what the candidate wants to do is different from what they've been doing, you know there's something they don't like or something they're trying to change.
This helps you figure out why they left their last job, what they're looking for, and what they hope to get from it. It's much more instructive than asking "why you're leaving," which will probably just make them lie.
Related: 5 Lessons Nonprofit Leaders Can Learn from Big Tech
Closing the interview
These two questions also give you all the ammunition you need to close a candidate you want to hire. I had one candidate tell me they were leaving their last job because of their work-life balance. Did I promise them a better work-life balance if they came to work for me?
Even though I was reasonably sure I could provide exactly that, there was no need to spell it out and offer it explicitly — which would have forced me to start negotiations from a position with no power. Instead, I just steered the conversation towards my daughter's softball games, and casually mentioned that I never missed one.
The candidate read between the lines and took it from there.
Listening is the most important skill you can develop as an interviewer, and if your candidates are worthwhile, they'll listen just as carefully to how you answer their questions. So remember: don't treat people the way you need to be treated; treat them the way they need to be treated.
Pitching someone the idea of coming to work for you is the same as selling them a house. They have to be able to see themselves living and growing there. That's why you have to tell them a good story and then give them the tools to keep writing it.
The interview is the start of that story. If you listen carefully, they'll show you exactly where they want it to go. From there, it's a simple matter of choosing whether that's the story you want to help them tell.
Related: Are You Really Listening? 7 Barriers to Listening Effectively
