CEOs are notoriously eccentric, but they got where they are by picking the brightest people to join them.
While we're admittedly not fans of questions aimed at discombobulating a job candidate, we do like questions that dive into a candidate's talents, achievements, motivation, and passion.
Our favorite interview questions are smart questions that require creativity, self-reflection, and empathy to answer.
Often known as behavioral questions, there are the kinds of good questions that don't have a "correct" answer. Instead, the answer gives real insight into a candidate's best traits.
But wait! There's more. Job interviews are also your chance to determine if the company is a good fit for you. If you're in a final round of interviews and you get access to the CEO, make it count!
Use your access to your potential new boss to ask them behavioral questions, too. Find out what their leadership style is like, how their mission aligns with what you've learned about the company, and whether this place is a long-term fit for you.
Here are some CEO interview questions to prepare to answer and to ask. Yes, all of these questions can be volleyed right back. Use these questions to learn more about the CEO's role, the company's vision, the company values, and how you might fit into it all.
Table of Contents
- What Do You Like to Do for Fun?
- Tell Me About Some of the Most Difficult Problems You Encountered.
- Tell Me About Your Background.
- Tell Me About This [xyz] Career Decision or Career Transition.
- Give Me an Example of a Time When You Solved an Analytically Difficult Problem.
- If You Find Yourself in Situations Where They're Not Going the Way You Want Them to, What Do You Do?
- Describe Some Difficult Leadership Situations and How You Managed People Through Them.
- A Curveball: Find Out How They Treat Others
- Describe a Failure in Your Career.
1. "What Do You Like to Do for Fun?"
CEOs love this interview question because it "always speaks volumes of who that person is. This question can determine a cultural add within the company and tell more about who a candidate is—through and through.
How to Answer This Style of Question:
This is a culture fit question through and through. The idea behind these is that you should know the company and have considered whether you'd make an excellent addition to the personalities there.
The best way to prepare for these sorts of questions is to do your research thoroughly. Because if you loved Warby Parker, shouldn't you know that they like their team to have a little fun? (I mean, those glasses look fun).
Red Flag Alert:
If you read above, notice we used the term "culture add", not "culture fit". If you feel this question is aimed to have you answer that you love the same things, it might be a red flag.
Be you in the interview, If the hiring manager doesn't "get" your interest in crocheting or long-distance running, that's their own problem!
2. "Tell Me About Some of the Most Difficult Problems You Encountered."
This is a pretty common interview question, but you want to make sure to have an impressive answer. The CEO likely wants to know which of your characteristics came into play when faced with a high-stakes problem.
How did you address the problem? How long did it take? Did you take a leadership role to solve the issue? What was the outcome?
Using story circles and the STAR method is a great way to "write" these stories from your perspective so that you're ready to tell them in an interview setting.
Pro Storytelling Tip:
Tell this story a few times out loud.
Each time, try to remember new and exciting details that could place your interviewer in that moment of time. Don't lie or embellish your answer but do make it compelling.
How to Answer This Style of Question:
Know yourself and prepare to answer questions about problems and mistakes—they come up more frequently than most job seekers expect. Also, feel free to pause and linger on a question when it's hard-hitting like this.
3. "Tell Me About Your Background."
A deceptively simple and all-too-common interview question, this is a common question for a very good reason. It’s a great way to warm up any conversation, and it really helps me understand how you communicate.
Are you linear, concise, and direct? Or are you a storyteller? Are you entertaining? Do you go off on tangents?
How to Answer This Style of Question:
When you're unprepared for this question, you will spiral. What do they want to know? How can I summarize my entire being?
Take some tie to distill the important parts of your background—specifically with how they relate to the role. We're not telling you to share that you knew you wanted to be a social media manager when you received your first email in 1999.
Think about the company's values, your biggest accomplishments, and the recent events in your career that led you to this interview. If you want to sprinkle in a few fun facts about yourself, then share those, too!
4. "Tell Me About This [xyz] Career Decision or Career Transition."
Apparently, former SoulCycle CEO Melanie Whelan also likes to ask questions about career transitions to see how interviewees approach them. "Were you running away from something or toward something, and how do you frame that?"
How to Answer This Style of Question:
Know your personal pitch and know how to tell a story well.
That includes being able to talk about gaps in your resume or shifts between industries. If you're not comfortable talking about yourself, you need to work on it either with friends or by joining a local Toastmasters or something of the sort. This is a type of public speaking and how you articulate your background is absolutely key.
5. "Give Me an Example of a Time When You Solved an Analytically Difficult Problem."
This is what you might call a "behavioral" interview question. Here's how Laszlo Bock, CEO of Humu, explains behavioral interviewing to the New York Times:
"'You're not giving someone a hypothetical, but you're starting with a question like, 'Give me an example of a time when you solved an analytically difficult problem.'"
"You get to see how they actually interacted in a real-world situation, and the valuable 'meta' information you get about the candidate is a sense of what they consider to be difficult."
How to Answer This Style of Question:
Don't be afraid to get real, in fact, that's the point. Pull an actual example from the last few months. If you're not self-reflecting on your work, you should be. One way to do this is to start keeping a work journal of your successes and failures right now.
6. "If You Find Yourself in Situations Where They're Not Going the Way You Want Them to, What Do You Do?"
According to an interview with the New York Times, TIAA Financial Solutions CEO Lori Dickerson Fouché—uses this question to gauge how a candidate conducts themselves under pressure. She also asks:
7. "Describe Some Difficult Leadership Situations and How You Managed People Through Them."
This is a question CEOs ask for higher-level positions to gauge "how they make their own hiring and firing decisions."
How to Answer This Style of Question:
These may seem like different questions, but according to Fouché, each focuses on "perseverance and resilience"—great qualities to have especially at the bigger companies where she's worked.
Approach these with a critical eye. Explain how you work, but also why. And don't be afraid to mention a moment where you misstepped early on. Share how you learned something essential about how you work or how you lead.
8. A Curveball: Find Out How They Treat Others
No, this isn't a question for you. It's for the receptionist who you checked in with and maybe the person who rode the elevator up with you, too.
Sometimes, the best way to understand a job candidate is to ask people how they behaved when it didn't occur to them that anyone was paying attention.
It's a way to get "a sense of the 'non-cognitive skills' that good leaders need to manage and inspire teams.
Pay Attention to CEO's Treatment of Others:
This is an even more important question for you, the candidate, to consider. How a CEO treats others trickles down to other senior management, and it becomes interwoven with the entire company culture.
Maybe this isn't as important to you. Perhaps you'd love to work for a "mad genius" type of CEO who gets kicks from being demeaning to baristas.
If the CEO has a reputation for being short, cold, and uninviting, is that okay with you? Does the CEO treat maintenance with the same respect they give to a big investor?
However, if this is important to you, pay attention. Treat everyone like they could be the company's CEO. From our perspective, how you treat others is of utmost importance.
Every human interaction is important. Kindness matters and it's as contagious as rudeness—the question is, which contagion would you like to catch at your next job?
9. Horror Stories: "Describe a Failure in Your Career."
Mistakes happen. Yes, they do—and it's ok. It's what you learn from your failures and mistakes that makes a big difference.
CEOs ask this question to determine how a potential employee approaches and overcomes problems. This also can illustrate the candidate's ability to take responsibility, bounce back, and refocus after problems occur.
This is a great question to ask because it takes the CEO out of their current role of power. It allows for vulnerability (depending on their willingness to answer!) and real insight into how this leader handles some of their own biggest challenges.
If you're talking to a startup founder, you might want to reserve a few minutes to talk about all the failures, detours, redirects, and rebounds.
It's pretty exciting stuff!
How to Do This Right:
Next time you're going out for interviews, make sure you have your best failure ready—and the step-by-step recourse that you followed after the failure.
How did this failure inform how you moved forward? What actions do you take to ensure that it doesn't happen again?
