The 9 best interview questions to ask according to 1,000+ managers

The question, “What are the best interview questions to ask?” was recently discussed in The Watercooler, our online community of 1,000+ managers. Here were their answers.

Best interview questions

You only have one hour with this person, so you need to decide: What are the best interview questions to ask them?

Hiring is one of the hardest parts of our job as a manager. When you think about it, it’s actually a bit nuts how we go about it. In an extremely isolated and condensed amount of time, we have to figure out whether or not a person would positively contribute to our team. We’re literally trying to project out the next few years based off a handful of hours of interaction with this person.

Given the limited context you have, what becomes paramount in the hiring process are the interview questions themselves – and what you listen for in the response. Yes, reference calls are undoubtably important the hiring process. And, I’m personally a big advocate of having a potential new hire do some small contract work or taking home a project and compensating them. But the interview itself is a rare opportunity to hear the candidate themselves – to have them unpack their thinking, share what’s influenced them, and reveal to you what’s most important in their life. So paying close attention to what you ask, and what you’re taking in, is key.

“What are your best interview questions?” was a big topic of conversation in our online community, The Watercooler, with over 1,000 managers. In addition to sharing their favorite interview questions, members also shared why they choose to ask those questions and what to listen for. From this conversation, I pulled what I saw as the 9 best interview questions to ask. In no particular order…

#1: If you had an entire work day with no meetings, obligations, or interruptions – what would you do?

The Watercooler member who suggested this described how he looks for both how a person answers (e.g., do they give a time-based or sequenced schedule, or is their answer more conceptual?) and what someone might say (e.g., are they data-oriented or people-oriented?) – and he tries to match their answers to the role.

#2: What is the project that you are most proud of?

You can ask this question to get a sense for what kind of work excites someone, and the degree to which they get excited about it. Wrote one Watercooler member: “I’m looking for passion and shining eyes when they are answering the question.”

#3: Where do you see your career in a year, and how does this role help you get there?

According to a Watercooler member, the answers to this question demonstrate how well candidates understand their personal and professional development goals, the specific position they are interviewing for, and how the position they are interviewing for impacts the company.

#4: How do you know you’ve had a productive day at the office?

This question is helpful for understanding how a person defines their own sense of productivity: Is it based on number of hours worked? Is it based on how much they’re learning? Oftentimes, you’ll figure out if someone can work not just hard, but work smart.

#5: Can you describe a company you would love to work in?

One Watercooler member recommended asking this question because he “[doesn’t] want to hire a someone who highly values something we can’t provide.” In short, these questions help calibrate values, fit, and expectations.

#6: Tell me about a time when you experienced frustration, and how you handled it.

This question is “a good window into the way people deal with stress and with interpersonal conflict,” noted a Watercooler member. From their experience, and answers have ranged from, “Life is all about relationships, so I go to the person who’s frustrating me and listen empathetically,” to “I demanded a new position from my boss over and over again even though he kept saying no,” to “I got fed up and quit”.

#7: What are the qualities you like least and most in your parents?

A Watercooler member noticed that asking this question “immediately takes the conversation away from the canned track of “my main flaw is my attention to detail” responses. And it provides them with an opportunity to be real and honest.” It also speaks to a person’s core personal values.

#8: What three events in your life would you say have had the biggest impact on your and why?

Ask this question instead of the standard, “Tell me a little bit about yourself”, as this helps reveal to me what they consider important and what they feel has shaped and motivated them.

#9: Let’s say you were to be in this role – what would your biggest learning curve be?

When you ask this question, you can get a sense of a person’s self-awareness and humility. Can they list a bunch of things easily (perhaps, too easily)? Or are they unwilling to admit where they might struggle?


You may only have an hour or so, but try one of these questions the next time you have an interview with a candidate. You’ll likely learn something about them you wouldn’t have learned otherwise.

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Written by Claire Lew

CEO of Know Your Team. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.

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