Eight Essential Interview Questions CEOs Swear By

“If time, money, and talent were no object, what would you do?”

That was the question that Saundra Pelletier, CEO of Evofem Biosciences, shared with me when I asked her how she interviews job candidates — one of the themes that I often explored with chief executives in the weekly “Corner Office” series I created and ran for a decade at The New York Times.

Pelletier’s question is just one of many surprising hiring approaches I’ve learned about over the course of more than 1,000 interviews with leaders, published in the Times and now on LinkedIn, over the past 15 years. Through all those conversations, I’ve amassed a large data set of questions that leaders use as a work-around to avoid the pat and predictable answers that job candidates recycle in response to standard hiring questions. Some leaders have come up with “bank shot” questions to get around the polished facades that people present in interviews so that they can better understand who candidates really are.

To categorize all of the interview questions I’ve heard over the years, I sorted them into what I call essential questions — the core questions that the interviewer is trying to answer about the candidate as part of their key checklist. For example: Are they self-aware? Are they a team player? Do they have a strong sense of personal accountability and responsibility? In an ideal world, it would be more efficient to simply pose those questions and get an honest yes-or-no answer. But many people are quite savvy about offering up answers that they think the interviewer wants to hear.

The bank-shot questions below require meaningful and authentic answers that candidates can’t take from a cookie-cutter script, even if they’ve been asked them before.

Essential Question 1: Do You Really Want to Work Here?

It’s a natural first question for an employer: Is the candidate simply playing a numbers game by blasting out 100 applications to different companies? You want to know that the candidate has done their research and has authentic and meaningful reasons for wanting to work at your company rather than just wanting to land a job.

Some bank-shot questions to probe their level of interest include:

• What have you learned about our company beyond what you’ve read on the website?
• What do you think you might be able to do that’s different from what we’ve done?
• Why is our company and this job the right next step in your professional and personal journey?

Susan Salka, the former CEO of AMN Healthcare, shared her rationale for asking the third question: “I find that when I ask the question that way, people open up about where they are in their professional journey. I don’t want somebody who just sees this as a job. I want it to be really important in their life somehow.”

Essential Question 2: What Makes You Tick?

Given the level of disruption in the world, and the fact that every company is in some phase of transforming itself, any job that someone is hired for is likely to change. So employers want to understand a candidate’s strengths, their work ethic, and the source of their drive.

Bank-shot questions:

• What were important early influences that shaped who you are as a leader and colleague?
• What do you enjoy the most and the least in your current job? When are you in a state of flow?
• How do you define professional fulfillment?

This last question is a favorite of Marcus Ryu, a partner at Battery Ventures and the former CEO and a cofounder of Guidewire Software. “I find that it’s very hard for people to lie about that question because stock answers sound so phony,” he said. “People who have reflected on that generally can speak from the heart.”

Essential Question 3: Do You Have a High Level of Personal Accountability and Determination?

It is a crucial moment in any relationship between an employer and employee: You have a difficult assignment with no obvious solution, many gray areas, and plenty of challenges. Do they push back, coming up with reasons why it can’t be done? Or does the employee ask for more clarity and say, in so many words, “I’ve got this and I’ll figure it out”? Whatever you call it — grit, perseverance, resilience, or comfort with ambiguity — all employers want this resourceful quality in their new hires.

Bank-shot questions:

• What was the hardest problem you’ve faced, and how did you handle it? Why was it hard?
• What leadership muscles did you build or strengthen during the intense period of disruption caused by the pandemic?
• How have you led change in previous roles?

That ability to lead change is essential for Sabine Heller, a veteran C-suite executive. “I want to know if that person has been able to come up with an idea, build consensus for that idea, and follow it through,” she said. “I want to see if they are a leader in one way or another. You need someone who can manage laterally and get people on board with their ideas.”

Essential Question 4: Are You Hungry to Learn and Build New Skills?

The current shorthand in the corporate world for this quality is growth mindset, a term popularized by psychologist Carol Dweck. Others have described it simply as curiosity. But it is a habit of mind that is essential for success. Companies are looking for employees with an innate hunger to learn more and raise their game rather than rest on past successes.

Bank-shot questions:

• What idea, challenge, or question has captured your interest and is driving you to learn more about it now?
• If your core expertise is your “major,” what is your professional “minor”? What interests you and why?
• How do you want to be better at your job over the next two years? What will you do to achieve that?

The third question is from Niki Leondakis, the CEO of CorePower Yoga. “If someone can’t answer that honestly and rather quickly, if you have to think too hard about what you’re working on developing, are you really working on it?” she said.

Essential Question 5: Are You a Team Player?

I have often worked in the following joke during talks I’ve given to audiences or while I’ve been running offsites for leadership teams: “There’s a reason HBO always ran Game of Thrones on Sunday night — to get people ready for work on Monday.” It always gets an uncomfortable laugh because anybody who has spent a few years in the workforce has encountered the kind of colleague who sees everything as a zero-sum game: If they are going to win, somebody else is going to have to lose. Employers want to steer clear of those job candidates, regardless of how talented they are, and instead find people who are wired to help their colleagues and understand the power of teams.

Bank-shot questions:

• What is your playbook for influencing people who don’t report to you?
• What was the best and worst team you’ve worked on? What were the dynamics of each of them?
• How do you deal with difficult interpersonal issues at work?

Tachi Yamada, the late former chief medical and scientific officer of Takeda Pharmaceuticals, explained his approach in asking this last question when I interviewed him in 2010: “Intelligence is often more displayed in what I would call complex abstract thinking, and there’s nothing more complex and abstract than human relationships. And if they can work their way through a human relationship problem intelligently, my guess is that they’re very smart people.”

Essential Question 6: Are You Self-Aware?

There are always gaps between how we think we are showing up in the world and how people perceive us. But there is no such thing as misperception in terms of how you are viewed by colleagues. If they think you are a bad listener or disengaged or quick to point fingers and blame others, that is all that matters. To be an effective team player and leader, you must be self-aware so that you not only understand your strengths and weaknesses but also how others see you.

Bank-shot questions:

• What’s the most surprising negative feedback you’ve received, and what did you do about it?
• Six months from now, what are we going to learn about you that we have no idea about right now?
• What are your triggers, and how do you manage them?

The third question comes from Corey Thomas, the CEO of Rapid7, a cybersecurity company. “If an executive can’t answer what their triggers are, that’s a nonstarter,” he said. “We all have them, and if you’re not aware of them, that probably means you lack maturity around them.”

Essential Question 7: Will You Thrive in Our Culture?

Many companies look for “cultural fit” in their new hires. Given that a focus on fit can undermine efforts to improve diversity, equity, and inclusion, that thinking has shifted to hiring people who will be cultural enhancers. Employers want people who know how to read the room and understand the nuances of the existing culture before trying to help strengthen it.

Bank-shot questions:

• What did you like the most and least about previous cultures you worked in?
• How did you “merge into traffic” with a new culture when you changed jobs in the past?
• What are the lasting fingerprints you’ve left in previous companies where you’ve worked?

That last question is from Laurie Havanec, chief people officer at CVS Health. “I define fingerprints as strategic initiatives that you’re proud of and that endure after you’ve left,” she said. “When people talk about their fingerprints, you learn a lot about how they think, how they innovate, how they lead, and how they measure results.”

Essential Question 8: Are You an Effective Leader?

The stakes are higher if you’re interviewing someone for a manager or leadership role, given the impact that the person is going to have on the broader team. Does the person understand the complexities and balancing acts that make leadership roles so challenging? Do they have both hard skills for driving results and soft skills for coaching people on their team and building followership? Can they develop other leaders?

Bank-shot questions:

• If you took over a new team, what would you tell them are the three most important values to you as a leader and how those values became important to you?
• When you mentor and coach people, what are the most common themes that come up in those conversations?
• How do you ensure that your teams operate like true teams?
• How do you challenge your own assumptions?

This last question crystallizes a theme leaders underscored: the challenge of being decisive while also questioning the underlying logic of their decisions. Penny Herscher, a veteran tech CEO and board director, shared that she often will draw leaders’ attention to that inherent tension of believing that they know the answers while also being honest with themselves about what they don’t know. To provoke their thinking, she will ask them, “What would have to be true for you to be wrong?”

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It is a universal mantra in businesses that “our employees are our greatest assets” and that the war for talent is the most crucial competition organizations face. A focused and intentional interview process — one with greater clarity around the qualities a company wants in candidates and effective ways to probe for those qualities — will help businesses improve their odds of making a great hire.