Making sure a company is right for your next steps requires careful consideration. We asked industry experts to share one question they always ask in a job interview that helps them determine if the company is the right fit—and what insight they gain from the answer. By asking these strategic questions, you’ll gain valuable information about company culture, growth opportunities, and potential challenges, so you can determine if the position aligns with your career goals.
- Uncover Hidden Job Expectations
- Probe Team’s Self-Awareness and Challenges
- Explore Company’s Adaptability to Change
- Assess Openness to Diverse Perspectives
- Clarify Role Expectations and Success Metrics
- Understand Growth and Compensation Processes
- Evaluate Team’s Approach to Failure
- Test Company’s Tolerance for Disagreement
- Reveal Team’s Response to Failure
- Examine Crisis Management Strategies
- Uncover Post-Hire Revelations About Company
- Investigate Handling of Employee Struggles
- Discover Personal Motivations for Staying
- Assess Problem-Solving Culture
- Learn from Long-Standing Team Members
- Explore Professional Development Opportunities
How to Find the Right Company: 16 Questions to Ask in Your Next Job Interview
Uncover Hidden Job Expectations
I am going to share the one question I tell job seekers to ask in every interview to discover if the company is a great fit:
“What is not listed in the job description that you really hope I bring to the table on day 1?”
There is a reason I recommend this: I discovered by working with recruiters that not everything can make it into the job posting. At times the hiring manager has some strong opinions, or sometimes they simply cannot use certain words because it would attract the wrong job applicants.
But when you ask this question, you really break the ice. You let the hiring manager know, “I want to work with you. What do you care about most?”
And that answer you receive may tell you, “RUN!” or, “I think I am going to like it here!”
Let me give you some real responses I heard after asking this question:
“If I have one more applicant tell me they know Excel, but doesn’t even know how to use functions, I’m going to scream!”
And then, there was this:
“I really need someone who knows the life sciences space, not just an environmentalist.”
As a job seeker, you can understand a great deal about what the company is going through by the temperament of the hiring manager.
And if you sympathize with that hiring manager, you may have just found the perfect place to work and the perfect people to work for.
Steven Lowell
Sr. Reverse Recruiter & Career Coach, Find My Profession
Probe Team’s Self-Awareness and Challenges
We’ve helped over 2 million people land better jobs by helping them sharpen not just their resumes, but their strategy. One thing I always tell job seekers is that their interviews aren’t just about getting chosen but also about choosing wisely. You’re not just evaluating a salary or a title. You’re evaluating what kind of environment you’re stepping into.
That’s why the one question I always ask in a job interview is, “What’s something this team is still figuring out?”
It’s a simple question, yes, but a straightforward one. And often a question that no one would ever think of, but it opens the door to real insight. First, it tells me how self-aware the company is. Do they acknowledge friction? Are they willing to talk about what’s not perfect? Because every team has rough edges, but what matters is whether they’re honest about it. If they say nothing or give a vague answer, that’s usually a telltale sign of what is happening inside. It signals a culture that masks problems instead of solving them.
However, when someone provides a thoughtful, specific answer, such as “We’re still trying to improve how we onboard remote hires,” or “We’re figuring out how to scale without losing our team dynamic,” that tells me something valuable. It shows they’re paying attention. It shows there’s room to contribute beyond just the job description. And it often tells me more about the day-to-day reality than anything on the company website.
For me, that question cuts through the performance and gives you a glimpse of what working there might feel like. You learn how they handle imperfection. And you understand whether your strengths would matter in that environment.
Stephen Greet
CEO & Co-Founder, BeamJobs
Explore Company’s Adaptability to Change
One question that tends to reveal a lot is, “Can you describe a time when the company went through a significant change? How did it affect the team and decision-making process?” This question digs deep into the company’s adaptability and transparency. From the answer, you can gauge how the company communicates during uncertain times, how resilient the team culture is, and whether employees are included in the narrative or left in the dark. It also hints at how much the company values employee input during challenging shifts. This can provide a clearer picture of whether the company truly aligns with your own values of growth and inclusivity.
Sinoun Chea
CEO and Founder, ShiftWeb
Assess Openness to Diverse Perspectives
I would ask hiring managers, “Can you describe when someone on your team brought an unpopular idea forward—and what happened next?” By framing it this way, I’m not fishing for a rehearsed success story; I want to hear the real dynamics of debate, decision-making, and follow-through. It reveals whether the company genuinely values diverse perspectives or merely pays lip service to “innovation.” If they can point to a concrete example—complete with who spoke up, how leadership handled resistance, and what changed—it tells me they empower psychological safety and value every voice.
Kristin Marquet
Founder & Creative Director, Marquet Media
Clarify Role Expectations and Success Metrics
One question I always ask is: “What does success look like in this role after six months, and how is that measured?”
The way someone answers tells me everything about how clearly the company defines expectations, how they support new hires, and whether they value outcomes over activity. If the answer is vague or focused only on being “a good cultural fit,” that’s a red flag. It usually means priorities aren’t aligned or accountability isn’t clear.
On the other hand, a specific answer with real examples gives me confidence that the team knows what it’s solving for and how performance is recognized. That insight helps me decide if I’m stepping into a growth environment or just a seat at a desk.
Mel Trari
Marketing Manager, InterviewPal
Understand Growth and Compensation Processes
One thing I always ask in an interview is, “Can you walk me through how your team does performance reviews, promotions, and salary increases?” This question is a starting point for understanding not only the company’s structure but also its underlying values.
If they tell me, for example, that those reviews are annual occurrences, linked to measurable goals and clear benchmarks, I know they take growth seriously and have a clear system in place. On the other hand, if they provide a vague answer, such as “it depends” or “we’re pretty flexible,” I take that as a red flag—it often means promotions and raises are arbitrary or subject to the whims of leadership, and that can be frustrating in the long term.
Clearly defined review cycles are more successful in retaining and keeping satisfied employees. For instance, bi-annual feedback with documented paths to growth and raises between 3 and 5% are more effective in maintaining employee satisfaction and retention, at least according to my own experiences both as an employee and as a manager.
It’s also beneficial for me to be able to determine whether I’ll have room to grow or whether I’ll have to fight for every step forward. I encourage candidates to ask this question sooner rather than later because it’s not just about money, but whether the company believes fostering your growth is important to the culture of the company.
John Pennypacker
VP of Marketing & Sales, Deep Cognition
Evaluate Team’s Approach to Failure
I love the question: “Can you tell me about a project that didn’t go according to plan, how the team handled it, and what you learned from it?”
It provides vital information about how the team handles stress, how they deal with failure, if they learn from their mistakes, and if they hold a growth mindset.
How we respond to our failures says everything about us.
It’s a red flag if they can’t acknowledge any failures, or if they demonize failure as a “bad thing.” However, if the company embraces failure as a part of learning and seems to love growth and feedback, then that tells you a lot about them.
Cara Heilmann
President, International Association of Career Coaches
Test Company’s Tolerance for Disagreement
One question I always ask in a job interview, especially when I’m on the candidate side or advising someone who is, is this:
“Can you tell me about a time someone disagreed with leadership, and how it played out?”
In my experience running multiple ventures, you’ll learn a lot about a company’s culture from how it handles friction. If they pause, shift tone, or give a rehearsed answer, that tells me disagreement isn’t welcome. However, if they can point to a real example where someone challenged an idea, was heard, and still had a future at the company, that’s a sign of psychological safety and trust to me.
For me, it’s not about conflict for the sake of conflict. It’s about knowing whether the organization values real thinking or just quiet compliance. Because in my view, no matter how good the product or the perks are, if intelligent people can’t challenge ideas, that company’s not going to scale well, and I wouldn’t want to be part of it.
Jeff Mains
Founder and CEO, Champion Leadership Group
Reveal Team’s Response to Failure
I always ask: “Tell me about a time you failed—and how your team handled it.” The answer reveals character, communication style, and emotional intelligence.
If someone blames others or downplays failure, it’s a red flag. We seek team members who view failure as a source of fuel. That response tells me whether they fit our Ubuntu-based culture: “I am because we are.”
Blake Renda
Founder / Managing Partner / Co-CEO, Dragon Horse Agency
Examine Crisis Management Strategies
“How did the company respond to the last serious crisis or unforeseen situation?”
The answer tells me how resilient the team is to stress, how quickly it adapts, and whether there is room in the company culture for open analysis of mistakes. This is especially important in development, where there are always risks and changes during the project.
Ivan Vinogradov
CEO, IKON Development
Uncover Post-Hire Revelations About Company
“What surprised you about the company after you joined?”
This question allows the interviewer to go in either a positive or negative direction, which can provide insight into the company’s internal culture. The interviewer’s tone can reveal a great deal about whether it’s the type of company you want to work for. If they reply with a positive surprise as their first instinct, it’s a great sign.
Colin McIntosh
Founder, Sheets AI Resume Builder
Investigate Handling of Employee Struggles
Most people focus on impressing interviewers. I recommend a question that flips that dynamic. Something like…
“Tell me about the last person who failed in this role. What happened, and how was it handled?”
This highlights how the company manages stress. Because everyone struggles at some point, and their response says a lot about their leadership culture.
If they can’t or won’t answer, that’s a red flag. And if they immediately get defensive, you’ve just seen how feedback works in that situation.
The best answers to this sort of question acknowledge both the organization and the employee. They’ll explain what they learned, what they changed, and how they supported the person, even if that meant helping them exit.
If the interviewer proudly explains that they “cut the dead weight quickly” without mentioning coaching or support, avoid.
Kasia Siwosz
Life Coach for the Top 1%, Kasia Siwosz
Discover Personal Motivations for Staying
“What makes you personally continue choosing to work here?”
Asking this question directly to your interviewer provides you with an authentic perspective that goes beyond what’s typically presented in an official job description. Instead of hearing a generic, polished response, you receive firsthand insight into emotional satisfaction, personal motivations, and genuinely positive aspects of the company culture. How the interviewer answers this question can also reveal a lot between the lines:
If they respond naturally and enthusiastically, offering specific examples like supportive teamwork, meaningful growth opportunities, or alignment with personal values, that’s usually a positive sign.
On the other hand, if they seem hesitant, vague, or overly rehearsed about why they like working there, it may signal dissatisfaction or a culture misaligned with the values or experiences you’re seeking.
Bayu Prihandito
Psychology Consultant, Life Coach, Founder, Life Architekture
Assess Problem-Solving Culture
What tells me if a company is the right fit is how they handle things when they go wrong. That’s why I always ask, “What happens here when something breaks or doesn’t go according to plan?”
You can learn a great deal from the way they respond when discussing open conversations, team retrospectives, and learning from mistakes, which usually indicates a healthy environment. But if they become vague or shift the blame, that’s a red flag.
Over the years, I’ve learned that culture is most evident in the challenging moments, not during launch parties or team lunches. So I look for teams that stay calm, own problems together, and figure things out without pointing fingers.
This question helps me see whether I’ll be able to speak up, learn, and enjoy working with the team. It’s a simple question, but it tells me almost everything I need to know.
Nirmal Gyanwali
Website Designer, Nirmal Web Design Studio
Learn from Long-Standing Team Members
“Can you tell me about the longest-standing team member here? What do you love about how they work, and what could I learn from their nature?”
This question provides deep insight into the team culture, values, and what kind of behavior is truly appreciated. It reveals how the company defines loyalty, collaboration, and excellence. If the answer reflects qualities such as generosity, adaptability, mentorship, or quiet consistency, it tells me the workplace values character and long-term growth. If the response is vague or only focuses on output or results, it’s a red flag that people might be seen more as resources than team members.
Chris Mckenzie
Founder, Unlmtd Agency
Explore Professional Development Opportunities
When I was just starting out in my legal career, I always asked in a job interview, “How do you support and grow your team over time?” This question offers insight into the company’s approach to management, core values, and long-term thinking.
I’m not interested in general perks or buzzwords; I want to hear the details. Do they offer mentorship? Do managers provide ongoing feedback? Do they micromanage? Is there a budget for training or room for internal growth? When someone walks me through how they’ve helped a team member move up or overcome a challenge, that’s much more informative than any mission statement I’ve ever read.
This question has even helped me avoid teams that didn’t have clear or proactive leadership when I was earlier in my career. Now, as a law firm owner, I use the reverse lens—I explicitly share with people how I lead. I describe what feedback entails, how often we check in, and what growth paths we’ve charted for team roles.
If you are interviewing anywhere, take note of how confidently and specifically they answer this question. It not only tells you how they treat people but also how much they value them.
Seann Malloy
Founder & Managing Partner, Malloy Law Offices
