15 Insightful Interview Questions To Ask A Tech Job Applicant

If your company is hiring for a tech role, you’re likely looking to make a long-term hire—one who can add to the organization’s ongoing success. This is why an engaging interview is a pivotal point in the hiring process.

During the interview, it’s essential to ask thought-provoking questions to draw out applicants and find the best fit. However, it can be challenging to narrow down the right questions to ask within the limited time frame of an interview. For inspiration, borrow some of these insightful questions the members of Forbes Technology Council have asked their tech candidates.

‘What accomplishment are you most proud of?’

For me, it’s asking folks to highlight the accomplishments they are most proud of. How they overcome adversity, collaborate and share credit gives me an idea of how they would fit in our inclusive, collaborative culture. An immediate follow-up is usually, “What was your greatest failure or regret?” As an entrepreneurial company, hearing reflections on someone’s highs and lows is really insightful. – Neil Lampton, TIAG

‘Who is the most successful among your siblings/friends?’

I like to hire competitive people. My favorite question is, “Of all your siblings, who is the most successful, and why?” The right answer is “me.” The “why” gives you great insight into what motivates and drives the individual. If they have no siblings, you can substitute high school or college classmates or even childhood friends. – Dave Hart, Presidio

‘How would you handle an important deadline?’

The dynamics of the interview process have changed. As a clean energy company, the most important aspects I am looking for are alignment with our mission of making a positive impact on climate change and a drive to get results. Drive is important these days, since most people prefer to work remotely or in a hybrid format. So I think it’s important to ask, “If you have an important deadline, how do you handle that?” – Mo DuaWindESCo

‘What has been your biggest failure?’

I like to ask, “What has been your biggest failure, and what was different as a result?” I encourage candidates to choose from their personal or professional lives. Answers vary widely, and you get real insight into the candidate’s self-awareness, humility, adventurousness and resilience. The best team members stretch their boundaries, take ownership of their circumstances and results and become the best examples and leaders. –Phil Alberta, Next Phase Consulting

‘What’s keeping you from improving users’ lives?’

A telling question for me is, “What is stopping you from improving the lives of millions of users worldwide?” This question works in two ways: It expresses the company’s ambition to tackle global issues and it draws out the candidate’s character. Potential hires might talk about existing obstacles, or they could paint a vision with hypothetical solutions. Either way, it is a quick glimpse into their values and ambitions. – Tom Okman,Nord Security

‘How is your work self different from your interview self?’

It can be difficult to discern what a job candidate is really like, since they’re going to be on their A-game during the interview. So I ask, “How is ‘everyday-at-work-Thomas’ different from the ‘interview-Thomas’ we are speaking with now?” Their answer gives me insight into their self-awareness and reveals things about their style that can otherwise be difficult to know. – Peter Gregory, GCI Communications

‘How do you fit into this company’s puzzle?’

I ask long-term applicants an important question after explaining our company values, mission and products. My question is this: “How do you fit into our puzzle?” This seemingly simple question can help you learn what applicants hope to achieve with their knowledge and experience while working for your company. – Thomas Griffin,OptinMonster

‘What did you learn from a failed project?’

I say to the candidate, “Tell me about a project that failed. Why did it fail, and what did you learn? How did this make you a better tech developer/leader?” After a few years of experience, it would be very surprising to hear the candidate never failed at anything. What they make out of it is very revealing and a good gauge of their temperament and realism. – Laurent Philonenko, Servion Global Solutions

‘What makes you smile at work?’

Studies show that happy people are more productive and they work harder. So I ask, “What makes you smile at work?” I look for candidates who meet the technical requirements or can learn it quickly and are passionate about what they do. “Why?” is the follow-up question. It gives you future insight on how to keep them motivated. – Windy Nicholson,Salesforce

’Can you describe a past project you’re proud of?’

I like to ask the candidate to tell me about a project they worked on that they’re proud of. This is an open-ended question that reveals a lot about the candidate. If the candidate only talks about themselves and their role in the project, it may be a sign they’re not a team player. If the project doesn’t sound challenging, that may be a sign that the candidate avoids risk and plays it safe. – Dave Mariani, AtScale

‘What are your strengths and weaknesses?’

When hiring for the long term, it’s important to have an accurate picture of each candidate’s strengths and weaknesses. There’s no one better to ask than the candidates themselves. We ask, “What are your top three strengths and weaknesses?” It’s surprising how often candidates will provide thoughtful, accurate answers that prove to be invaluable in the hiring process. – William Bain, ScaleOut Software, Inc.

‘How have you dealt with a significant client issue?’

When interviewing for a technology leadership position, one portion of the interview I like to focus on is cultural fit. With that said, an insightful question to ask is how the candidate has dealt with a significant client issue. Responses will provide insights into their levels of engagement, transparency, empathy and ownership, as well as provide valuable next steps in resolving the issue. – Mark Schlesinger, Broadridge Financial Solutions

‘What happened the last time you and your boss disagreed?’

One thing I say is, “Tell me about the last time that you disagreed with your boss.” Understanding how someone expresses disagreement with their leaders is critical to a “disagree and commit” culture. I want to hire people who will be comfortable disagreeing with me and will express that disagreement directly. We cannot arrive at the best solutions unless people are willing to express alternative ideas. – Ken Knapton,Progrexion

‘How have you solved a technical problem on the job?’

I ask, “What was the last difficult technical problem you encountered on the job? How did you solve it?” I’m looking to garner some insights into their thought processes and problem-solving skills, as well as see how effective they are at communicating their processes back to me—someone with no context of the issue. As an added benefit, I get a better sense of what they deem “difficult.” – Rashad Nasir, ThinkCode

‘What one product would you like to focus on, and how would you develop it?’

I like to ask, “If budget wasn’t a factor and you could dedicate your time to one product, what would it be, and how would you develop it?” Many candidates talk about their perception of a product we’re building, which is interesting. But what I’m actually looking for is someone who is methodical and excited. People who are genuinely passionate tend to go the extra mile to get things done right. – Nicholas Domnisch, EE Solutions

Previously published on Forbes.