When Dave Vu interviews for roles, there’s one question he frequently gets asked: “Why would you want to deal with the challenges of a startup?” The first time he was asked that question, it stopped him in his tracks.

“It’s a simple but effective question that made me think about my motivation,” he said.

Now, Vu is more comfortable answering this question. Over the last decade, he’s helped run HR operations at a number of startups, and had a lot of time to figure out what it was that drew him to startup culture. As the VP of Talent at Montreal-based software company Local Logic, the question — why startups? — is one he’s excited to explain. 

“The reason why this question stuck with me is that it gave me pause to really think and ask myself why I would want to join the company,” he said. “When asked that question, it gets me excited for an opportunity when it is right.”

Examples of Open-Ended Interview Questions

  • What made you apply to this job?
  • What was a challenge you faced? And how did you handle it?
  • What are your weaknesses?
  • Tell me about a past mistake you made — how did you resolve it?
  • Have you ever disagreed with a coworker, and if so how did you approach that conflict?
  • How would your friends or family describe you?
  • What are three words you’d use to describe yourself?
  • What’s something about you that’s not on your resume?
  • What makes you excited to come to work?

That open-ended interview question helped Vu develop more self awareness and understand his own professional goals. It’s a lesson that Vu, who now handles Local Logic’s talent acquisition, has taken to heart.

“That question influenced my interview style,” he said. “It showed [me] that a well developed question can trigger a deep conversation that can uncover more about the person’s motivation, and allows for a better candidate experience.”

Asking the right open-ended questions in an interview can reveal a candidate’s internal drive, personality, decision making and thought process more than their resume alone ever could. Here are some tips from Vu and other HR leaders about the kinds of questions you should ask, which ones to avoid, and what open-ended interview questions can help you discover.

More on Job InterviewsHow to Do Panel Interviews Right

 

Read Between the Lines

Resumes give you information about a candidate’s qualifications, but a sheet of paper can only tell you so much. You need to give your applicants a chance to share the stories that couldn’t make it into their cover letter. Asking thoughtful, open-ended questions will give your candidate a better interview experience, and will help you make better hiring decisions.

“Open-ended questions give you a front row seat into someone’s thought process and personality,” said Kelly McGuinness, senior talent acquisition partner at New York-based remote IT company Electric. “The ability to answer quickly in a thoughtful way can show a lot of problem solving skills and give insight about how someone works behaviorally. It’s an opportunity for you to showcase your abilities and not just talk about what is on your resume.”

Let your knowledge about their background guide you, but use your interview time to look further and get to know your candidate as a person. This means not only listening to the answers they provide, but also reading subtle verbal or non-verbal cues that can clue you in to their behavioral patterns.

“Open-ended questions provide the candidate the opportunity to demonstrate their communication skills,” said Adam Redlich, VP of talent acquisition at New York-based fintech company Octane. “How they frame up their answers matters. Are they concise? Do they tend to babble? What is their thought process when approaching a problem they’re looking to solve?”

 

Stay on Track

During your interview, you should be trying to learn as much as you can about your interview subject by asking lots of questions. However, there are some questions you should try to avoid. It’s okay if your interview candidate wants to share some details about their personal life, but try to steer them toward topics relevant to their role, and don’t pry into anything that could be considered illegal.

“Avoid asking: Are you married? Are you close with your parents? Do you have children? How old are you?” said Lindsey Siegel, technical recruiting manager for fully distributed rewards platform Fetch Rewards. “These questions are not ethical or legal to ask. They also create a bias when answered.” 

Go beyond yes or no answers, but also remember being too open-ended with your questions can bewilder your interviewee and make you lose control over the interview. If you’ve ever been stumped by the “tell me about yourself” interview question, you know how hard it can be to come up with answers to broad questions. Don’t lead your candidate by explaining to much or asking multiple questions in one breath. Think about what information you actually want to know, and only ask what will help you get it. 

The scope of your questions is important, but so is the language you use to ask them. Framing a question the wrong way can confuse your interviewee or, worst case scenario, make them feel antagonized. 

“The biggest foible I’ve seen interviewers make, and train interviewers to not make, is asking questions that begin with why. Why did you make that decision? Why did you join that company?” said Redlich. “Why questions tend to put an interviewee on the defensive and often result in little useful information.  Instead, ask questions that begin with what or how — these questions invite more detail.”

As an example, let’s say you want to find out why an interviewee left their previous role. Asking them why they did that may make them feel like they have to justify their decision. However, asking what contributed to that decision and what they’re looking for now will open up the dialogue and encourage the candidate to make their desires clear.  

Find out who's hiring.
See jobs at top tech companies & startups
View All Jobs

 

Examples of Good Open-Ended Questions

What made you apply to this job?

Probably the easiest place to start an interview is by figuring out what drew your candidate to apply for your open role. This might seem like a straightforward question, but the answer your interviewee gives can tell you a lot about how much they’ve researched your company, what their ultimate professional goals are, and how they can see themselves on your team. 

“I look for candidates who can provide examples that are relevant to the role they’re interviewing for, as well as the organization as a whole,” said Siegel. “Candidates can set themself apart by showcasing the ways in which they can instantly add value and elevate the team.”

 

What was a challenge you faced? And how did you handle it?

A list of accomplishments, such as what you’d see in a resume, can’t give you the full picture of how they were achieved. On the pathway to any goal are challenges both large and small, and knowing how a candidate has handled such challenges in the past will tell you a lot about whether they’re someone you can rely on to solve similar challenges in the future. 

“This question helps me to learn about their problem solving skills, how they approach the problem, their solutions, resilience, communication and collaboration if they were working with others,” said Vu.  

Pay attention not only to the situation they’re describing, but the way they talk about it. If they can easily outline all the steps they took, take accountability for their past actions, and speak with confidence and a positive outlook, you can be nearly sure they’ll bring that energy to your company.

“Successful candidates are direct and succinct with their answers, and are ideally able to explain challenging situations and make them sound simple,” Siegel said. 

More on RecruitingWant to Make Tech a Better Place? Start With Inclusive Recruiting.

 

What are your weaknesses?

For most people, owning your accomplishments and strengths is a lot easier than owning your weaknesses. But part of accountability is knowing what you could do better, and a candidate who doesn’t shy away from discussing failures or setbacks shows they own their personal and professional growth. 

This question can provide clear insight about how well they’d fit in the role. For instance, if they’re interviewing for a public facing and team-oriented role, learning a candidate dislikes collaboration or seriously struggles with public speaking may be a dealbreaker. 

“Knowing where a person can improve will make it easier for the individual interviewing them to know if this is a skillset not as needed on the team,” said Siegel. “It makes hiring candidates smarter rather harder.”

 

What Should I Know That’s Not on Your Resume?

Just because the open role is the primary focus of your conversation doesn’t mean that has to be all you talk about. If you want to get a sense for who your candidate is off the clock, Redlich suggests asking them about what they do in their free time, or what was left off their resume. 

“This question is my ice breaker,” he said. “It gives me a bit of insight into what the candidate deems most important — do they mention they’re a huge fan of a sports team? Or do they talk about a particular hobby?”

Everyone has passions that lie outside of work, and giving your interviewee a chance to gush about them will help them feel more comfortable and also let their personality shine. You may also learn something that could make them a fit for the role that they otherwise wouldn’t have thought to bring up.

“Ask them about their hobbies outside of work, the last book they’ve read, or the last movie the’ve watched,” said Josh Jones, manager of talent acquisition at New York-based recruiting tech company Employ Inc. “Those questions can kind of loosen somebody up, and make you both a little bit more comfortable with each other.”

Find out who's hiring.
See jobs at top tech companies & startups
View All Jobs

 

Tell Me About a Past Mistake — How Did You Fix It?

You can’t expect your teammates to be perfect, but you can hope that they act with integrity and work to clean up their messes. That’s why asking potential employees about their own past mistakes is so important — if they deflect blame, point fingers, or downplay errors, they might not be a trustworthy member of your team. 

“[I ask] about a time when a project wasn’t going as planned and it became apparent that a deadline was going to be missed,” Redlich. “This question helps me understand if they are a team player, or if they play the blame-game.”

 

Have you ever disagreed with a coworker, and if so how did you approach that conflict?

Even employees at the most siloed offices still need to collaborate at times. Employers need to know that their new hires will be able to communicate effectively with their coworkers, especially during conflict. Asking your candidate about a time they disagreed with a coworker, similar to asking them about a past challenge, shows you how well they work under pressure and how they view their relationship to their peers. If they can approach conflict constructively and with a positive mindset, they’ll likely be an asset to your team.

“When I’ve hired people, I ask them about a time they had a disagreement with a coworker, and how they worked through it,” said Jones. “All jobs can be stressful in different ways, so you want to bring how someone handles and works through that to light.”

More on Job InterviewsUnstructured Vs. Structured Interviews: Which Is Better?

 

What Are three Words You’d Use to Describe Yourself?

What’s the most simple, straightforward way to find out someone’s personality or strong suits? Just ask them. Giving your candidate a chance to try describing themselves objectively will reveal a lot about how they view themselves, and how much self-awareness they have.

In a past interview, McGuinness said she was asked a variation of this question: What were three things her closest friends and family would say about her and why? That question, she said, pushed her to do some self-reflection.

“It forced me to dig deep, and helped me to understand that the job and company I was interviewing for wasn’t only worried about a specific skill set, but the type of person they were hiring,” she said.

Turning interview question responses, and the subtle clues hidden within them, into solid hiring decisions is tough. But knowing the right questions to ask is half the battle — the rest, Redlich said, just takes exercise.

“It takes time to gain the confidence to ask behavioral, open-ended questions and be able to read through the noise,” Redlich said. “Interviewing is as much art as it is science. Doing it well takes practice.”

Great Companies Need Great People. That's Where We Come In.

Recruit With Us