Crafting the perfect interview question list can take decades of experience. Instead of using questions you googled or have been asked in the past, take the fast track to getting a signal on your next hire with our roundup of questions from the experts on the HR Heretics podcast.
Check out the list of our top 7 questions here:
1. Ask about insecurities and how they manifest at work.
The question: What are your insecurities and how do they manifest themselves at work?
“I only use [this question] with very senior people,” said Colleen. Her reasoning? When she used the question at Credit Karma, she used it to break down barriers between her and the interviewee. She explained, “Anybody who was going to work in my group had to interview with me. I [asked the question] because I wanted them to not be scared of me and to make me more approachable.”
What insights do you get from the answer? “You learn how self-aware people are or are willing to be. And usually, the best candidates will come up with a ‘when I’m at my worst self, this is what I turn into’ response.”
The best response Colleen’s seen in her years of interviewing? Someone who was willing to admit they had grown up without a lot of resources so money had become their biggest motivator. When their money was at risk, their decision-making suffered. “We ended up hiring that person because they were totally honest,” said Colleen.
2. Ask about the kind of teammates a new hire needs to be around to be successful.
The question: What types of people do you need to be around to be successful?
Tom suggested interviewers use this question while checking in with references instead of asking about areas of weakness or opportunity. And his spin on the question really gets to the center of why the interview is such a good opportunity to find someone who is the right fit. He explained, “We all work together in teams, and great teams work in tension where the strengths of one balance the weaknesses of another.”
When you can figure out if the strengths of one team member will help aid in the weaknesses of another, you can build a team that will be successful. According to Tom, we have to think about the team's composition and what it needs to look like to succeed at different stages of the business.
The first step to asking this question? Get to know your current team members to know what type of new hire you need to find.
3. Ask about a time feedback was received poorly and how they handled it.
The question: What is a time you received feedback poorly? Walk me through your thought process on why that feedback was so hard for you to receive and why you handled it so poorly.
“My favorite question is a play on what’s the biggest mistake you’ve ever made,” said Melanie. With her version, the candidate is asked to walk the interviewer through a time they received feedback poorly and then their thought process on why they were so resistant to the feedback. “I think the why is more important,” said Melanie. “We’ve all received feedback poorly in the past. I want to understand what your triggers are…what you’re sensitive about…what context will throw you off and how you handle it.” The real insight comes not from the mistake the interviewee made, but what drives that person.
4. Ask why they want to join the company vs. a competitor.
The question: Why do you want to join this particular company? Why this company instead of all the others?
“I like to test my bullshit meter,” said Cara. And this question can send that meter to the top if the interviewee doesn’t have a good reason. “I think it’s a hard [question] too,” said Cara. “You’re either answering authentically or you’re not.”
For interviewees looking for a job in a high-growth technology company, it’s critical to have alignment with the company’s mission and vision. You need to believe in what they’re trying to accomplish. “You have to be able to internalize the reason you’re here because it’s hard,” said Cara. And if you make it to the other side—through those hard times—you get to see a completely different side of the business. “Once you have that 360, it’s insane. I will hire those people all day long,” said Cara.
5. Ask what their favorite boss would say about them.
Brett Queener, a partner at Bonfire Ventures with a background at Salesforce, Smart Recruiters, and others, shared his favorite interview question in episode 8 that can help sift through candidates who aren’t self-aware.
The question: Tell me what your favorite boss will say is great about you.
To get real results from Brett’s interview question, interviewers have to first ask interviewees about their favorite boss. Ask them to tell them about their favorite boss, what they loved and respected about them, why they were so great, etc. Get the boss’s name and contact information and explain to the interviewee that you’re going to call their boss tomorrow.
“We’ll get through the pleasantries, and then I’ll ask your boss for two one-sentence answers,” said Brett. “Can you give me one sentence on what is so great about this employee? And in your performance interviews, what was the one thing you were always giving them feedback about?”
Brett likes to double down on the performance review question, even if a previous manager doesn’t have a clear answer on what they gave feedback on regularly. One way to do that is to ask, ‘What did they have to get much better at to achieve their career goals?’
“What I’m really looking for here is self-awareness,” said Brett. He uses these questions and the reference calls to find out where candidates are strong, weak, and willing to be vulnerable to explain areas of improvement.
6. Ask the candidate to tell you their story.
Molly Graham, a seasoned exec, builder, and widely read writer in tech spoke about finding an interview style that works for her and the question she likes to start every interview with, no matter the position. Her interview is on episode 4 of HR Heretics.
The question: Tell me about your story.
“I have an interview style that works for me, and I don’t necessarily recommend it to other people,” said Molly. “The thing I recommend to other people is to find your interview style, the one that works for you.” For Molly, interviews flow better for her when she starts with a simple question—tell me about your story. She says people really open up, and by the end of the interview, she feels like she really knows them.
“I love where people go [with the question], and it helps me because I listen in a certain way, and I probe in a certain way. I ask questions in a certain way,” said Molly. She shared a story about one candidate who was the Head of Compensation at Facebook. He was born in Romania and became a refugee. “He told me his whole life story,” said Molly. “It was awesome, and I felt like I knew him by the end.”
7. Ask the candidate to walk you through their resume.
The question: Walk me through everything on your resume. Why did you leave each job? What are you most proud of?
Steve’s line of questioning for interviews is targeted at finding out how he and the business fit into the candidate’s story. “I’m trying to see what stands out. What boss was great, and what boss was a nightmare. What the key considerations were, etc,” said Steve.
Steve really wants to get the candidate to stop giving answers they think the interviewer wants to hear. “Let’s have a human conversation,” said Steve. “I want to know who you are.”
When the conversation becomes more human, interviewers can get to know who the candidate really is as a person. “What shaped me was my parents’ divorce,” said Steve. “Is that anywhere on my CV? No.” With this context, questions about adapting are easy to answer.
One thing to note from Steve’s episode, he thinks interviews are the worst predictors of hiring success. He explained, “Unfortunately, we don’t have a replacement [for interviews.] I wish the world would give us the opportunity for everyone to take a three-month pause every three years so we can try out another job. If we like it, we stay. If we don’t, we go back.”
Find the interview questions that work best for you.Consider this list as you prepare for your next interview or open position. With the right set of questions, you can get a quick signal on your candidates and find the new hire that will help your team succeed.
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