When you're hiring, especially in tech, the best candidates aren’t always the ones with the flashiest resumes, they’re the ones who bring curiosity, creativity, and a clear sense of self.
That’s where interesting interview questions come in. Moving beyond the usual “strengths and weaknesses” format can lead to honest conversations that give you real insight into how someone thinks, works, and fits with your team.
In a competitive hiring market, asking the unexpected can help you spot the right match faster.
Why Interesting Interview Questions Reveal More Than a Resume
While traditional interview questions still play an important role in assessing a candidate’s experience and technical skills, adding a few unexpected prompts can open the door to a more genuine conversation.
The Power of Catching Candidates Off Guard
These kinds of questions tend to catch candidates slightly off guard, not in a confrontational way, but just enough to steer them away from rehearsed answers.
That slight element of surprise often brings out more authentic responses, giving you a better sense of who the person is beyond their polished resume.
Unconventional questions can reveal how candidates think on their own, what truly motivates them, and how self-aware they are.
Why the Unfiltered Answers Matter
Since these aren’t the types of questions most people prepare for, their answers are more likely to reflect real thoughts, values, and instincts.
For a hiring manager, especially one building remote, that kind of insight is invaluable. It helps you look past the surface to find someone who not only has the skills but also the mindset and attitude that fit your company.
16 Unconventional Interview Questions to Inspire You
Questions about self
Even in a professional setting where technical skills matter, candidates bring their whole selves to work every day.
Understanding what they value outside of work can give you insight into how they’ll connect with your company culture and whether they’re a good fit for your team.
This first set of questions is designed to highlight the personal side of each candidate, what drives them, how they see the world, and what makes them unique.
1) What’s a personal interest or hobby you’re passionate about, and how has it shaped your life?
Why ask it:
This question helps reveal the candidate’s personality beyond the resume. You’ll get insights into what energizes them and how those passions might influence their approach to problem-solving, teamwork, or motivation in a professional setting.
2) If you could meet any famous person, living or not, who would it be and why?
Why ask it:
The answer can give you a glimpse into the candidate’s values, inspirations, and interests. Understanding who they admire and what they’d want to learn from that person can help paint a clearer picture of what drives and excites them.
3) If you could only do one activity for the rest of your life, what would it be and why?
Why ask it:
This question highlights what the candidate values most in their daily life. Whether it’s solving problems, helping others, or building things, their answer can uncover what kind of work or mindset they’re naturally drawn to.
4) What’s something that really gets under your skin and why?
Why ask it:
This question helps you understand how a candidate handles frustration and reacts to things that disrupt their flow. Their answer can shed light on how they operate in a team, how they deal with conflict, and what kind of work environment brings out their best.
If you’re hiring for a remote team, knowing where someone’s limits are is key to avoiding unnecessary friction.
5) In your own words, how do you define success in your career?
Why ask it:
Everyone chases success, but not everyone defines it the same way. This question helps you align expectations. A candidate’s answer gives you insight into what drives them, whether it's growth, impact, recognition, or continuous learning.
That kind of alignment is especially valuable when hiring remote software developers, where motivation and autonomy play a huge role in long-term performance.
6) What’s something about you that people tend to remember?
Why ask it:
This helps you gauge self-awareness and personal branding. It also gives a glimpse into how the candidate sees their unique value, something especially useful when you’re hiring for standout talent in a competitive field.
7) Can you teach me something you know well in just five minutes?
Why ask it:
This tests communication skills, clarity of thought, and how well they break down complex ideas, core traits for software developers who need to collaborate across teams or with non-technical stakeholders.
Questions about professional profile
A big part of any job interview is understanding how a candidate responds to everyday situations.
Asking focused questions about how they operate in a professional environment helps you uncover how they approach common challenges, collaborate with others, and make decisions on the job.
These insights are key to evaluating whether their work style aligns with what your team needs.
8) Is there anything about this role or company that concerns you?
Why ask it:
This opens the door for honest dialogue. You’ll learn what the candidate values in a work environment and whether they’ve thought critically about the opportunity, not just the paycheck.
9) What’s the boldest career move you’ve made and what did it teach you?
Why ask it:
This shows how a candidate handles risk and growth. You’ll get insight into their mindset when facing challenges and how they turn tough moments into learning opportunities.
10) If you could instantly change one thing about your last job, what would it be and why?
Why ask it:
This highlights what the candidate felt was missing or frustrating in a previous role. It helps you spot any red flags or opportunities to offer a better experience.
11) What three qualities do you bring to the table that would make a difference on the team?
Why ask it:
It pushes candidates to reflect on their strengths in a way that’s tied to business value. Their answer gives you a quick read on confidence, relevance, and cultural fit.
12) What sets you apart from other people applying for this role?
Why ask it:
This invites the candidate to connect their skills, background, or personality to the role in a meaningful way. It’s a great filter for identifying standouts.
13) How do you respond when your work is criticized by a manager?
Why ask it:
You’ll learn how the candidate handles feedback and whether they see it as a threat or a growth opportunity, crucial for building a feedback-friendly team culture.
Questions about decision making
While these questions are more personal, they can still reveal what the candidate prioritizes in life and how mindful they are about their choices.
14) If you had infinite money, how would you choose to spend your time and what would you do with the money?
Why ask it:
This helps you understand what motivates the candidate when external pressures are removed. It offers a window into their values, ambitions, and long-term vision.
15) You’re stuck on an island, but having water, food and shelter covered what three personal items would you want with you?
Why ask it:
A light, creative way to learn about the candidate’s personality and priorities. You’ll get hints about how they unwind, what they value, or how they problem-solve in unusual situations.
16) What’s the biggest decision you’ve made in the last year, and what came out of it?
Why ask it:
This reveals how a candidate approaches high-stakes situations and what they consider “big.” Their answer gives you insight into their judgment, confidence, and personal growth.
Getting the Most Value From Interesting Interview Questions
The goal with unconventional interview questions isn’t to find a “correct” answer, there usually isn’t one. Instead, you're giving candidates the space to share something personal or unfiltered, which helps you understand how they think, what they care about, and how they view the world.
These responses can reveal values, motivations, and even red flags that wouldn’t surface through standard questions.
To make this work, it’s important to set the tone early. Let the candidate know there’s no right or wrong answer and that you’re genuinely interested in hearing their honest perspective.
Look Beyond the Words
As you listen, try to look past the words themselves and consider what they say about the person behind them.
Sometimes, the most valuable insights come from how someone explains their answer or what they choose to focus on.
Don’t Skip the Follow-Up
It's OK to pause and ask a follow-up question if something stands out. Whether you’re curious about a specific choice they made or just want them to go a little deeper, follow-ups show that you’re engaged and also give the candidate another chance to open up.
When used thoughtfully, these questions can offer a deeper layer of understanding that helps you hire more intentionally.
Asking the Right Questions to Get the Best Talent
Interesting interview questions aren’t just a clever trick, they’re a simple and effective way to uncover qualities that match your current work culture.
When you’re intentional about how you use them, these questions go beyond surface-level answers and lead to conversations that actually tell you who a candidate is.
For founders, hiring managers, or team leads looking to build strong, reliable teams, that kind of clarity is worth more than a well-rehearsed response.
Ready to meet developers who bring more than just skills to the table? If you’re looking for developers who fit your team’s mindset and values, Strider can help.
Book a call and find skilled candidates today!
