10 Essential Questions to Ask a CEO in an Interview

Interviewing a CEO can be an incredible opportunity to gain insights from a top business leader.

But what should you ask to make the most of this valuable time?

In this ultimate guide, we’ll explore:

The questions that will impress any CEO and make you stand out
How to ask them tactfully to build rapport and get honest responses
What the CEO’s answers reveal and how to interpret them wisely

Powerful follow-up questions to dive deeper based on their replies

By the end of this article, you’ll be equipped with 10 thoughtful, impactful questions that will take your CEO interview to the next level.

Let’s get started!

Essential Questions to Ask a CEO in an Interview

What is your long-term vision for the company?

Kick off the interview by inviting the CEO to share their aspirations. You could say: “I’d love to hear about your long-term vision for [Company]. Where do you see things heading in the next 5-10 years?”

This open-ended question serves several purposes:

It allows the CEO to talk about something they’re passionate about – the future of their company. Most CEOs enjoy waxing eloquent about their plans.
It reveals how much thought they’ve given to long-term strategy. Have they painted a vivid picture with specific goals and milestones? Or do they seem uncertain?
It sheds light on their leadership style. Are they a visionary who thinks big and takes risks? Or more of a careful planner focused on incremental progress?

You can gauge their confidence and optimism. Do they speak enthusiastically about ambitious targets? Or do they sound hesitant and tempered in their expectations?

Listen closely and take notes. The CEO’s long-term vision is the North Star guiding the entire company. Understanding it provides valuable context for the rest of your discussion.

If their response is brief or vague, don’t hesitate to probe further. Ask what key trends or market forces are shaping their thinking. Inquire about the biggest obstacles they anticipate and how they plan to overcome them.

The CEO’s answers will give you a sense of how bold, creative, and realistic they are in their long-term planning. It’s a window into their mind as a strategist and leader.

How would you describe your leadership style and philosophy?

Next, shift the focus to the CEO’s approach to managing people. A simple way to broach the topic is: “What would you say is your leadership style or philosophy? How do you think about your role in guiding the team?”

The goal here is to better understand the CEO as a leader – their core beliefs, priorities, and methods. It’s a chance to see what makes them tick.

A strong answer will touch on things like:

Empowering employees to take ownership
Fostering open communication and transparency

Leading by example and building trust
Balancing direction-setting with autonomy
Emphasizing learning, growth, and development

Adapting flexibly to different people and situations

In contrast, a generic answer full of buzzwords should give you pause. If they can’t articulate a clear philosophy, they may lack self-awareness or struggle to connect with their team.

Also, note what they don’t mention. For example, if they say nothing about employee well-being or inclusion, those may not be top priorities.

The details matter too. When they share an anecdote or lesson learned, do they come across as humble and growth-oriented? Or a bit arrogant and set in their ways?

Leadership is both an art and a science. Look for signs that this CEO invests time reflecting on it and challenging themselves to improve. The best leaders are always working on their craft.

If you’re unsure about part of their answer, ask for clarification or a specific example. You want to leave with a vivid sense of how they show up as a leader day-to-day.

What are the company’s top priorities this year and why?

Steer the conversation toward the company’s immediate game plan. Try a question like: “Looking at the year ahead, what would you say are [Company’s] 3-5 most important priorities or initiatives?”

Unlike the long-term vision question, this one focuses on the near-term roadmap. It reveals the CEO’s judgment about what matters most right now.

A few things to listen for:

Alignment with the long-term vision. Do these priorities fit logically within the bigger picture they painted earlier? There should be a clear throughline.
Specificity and measurability. Vague priorities like “increase sales” suggest sloppy thinking. Look instead for crisp targets like “grow revenue 25% in the Northeast region.”
Balance across key areas. Are they covering the bases or overly focused on one domain? Thriving companies usually pursue a mix of priorities spanning product, growth, people, finance, etc.

Compelling rationale. For each priority, can the CEO explain exactly why it deserves outsized attention and resources now? Their reasoning is as important as the priority itself.
Employee buy-in. Have they communicated these priorities clearly across the org? And rallied people around them? If not, execution will likely suffer. Alignment starts at the top.

If the CEO struggles to name specific priorities, that’s a red flag. It’s their job to determine what’s most critical and galvanize the team to pursue it. Lack of clarity here often cascades downward.

Also, beware of constantly shifting priorities. While some evolution is inevitable, a new set every month creates chaos. Great CEOs are ruthless about pruning distractions and keeping the team focused.

The exact priorities will vary based on the company’s industry, stage, and competitive landscape. But this glimpse into the CEO’s near-term focus is invaluable for understanding the business context you’re walking into.

Can you tell me about a time you failed as a leader and what you learned from it?

Now it’s time for a zinger. With empathy in your voice, you might say something like: “We’ve all had leadership stumbles that taught us important lessons. Would you be willing to share an example of a time you failed as a leader and what wisdom you gained from it?”

This question is a direct test of the CEO’s self-awareness, humility, and growth mindset. Anyone who’s led for a meaningful period has failed. It comes with the territory. What separates good leaders from great ones is the ability to acknowledge and learn from those failures.

Tread lightly as you ask, though. The word “failure” will put some CEOs on the defensive. Emphasize that you’re not looking to play “gotcha” but rather to understand their resilience and maturity. If they seem reluctant, you can pivot to asking about a time they faced adversity or had to change course.

Still, the best CEOs will share a failure story openly, with a mix of vulnerability and wisdom. They’ll describe what went wrong, take responsibility for their role in it, and articulate specific lessons they’ve applied since.

You’re looking for a response with real substance – not a humblebrag in disguise or a failure so tiny it hardly counts. Gently probe both the ambiguity they felt in the moment and the scars that remain. Making hard decisions with incomplete information is a CEO’s daily reality. Managing the emotional toll is a learned skill.

If they’re unable to think of any failures, consider that a warning sign. Lack of awareness of one’s shortcomings often breeds overconfidence and unforced errors. CEO’s who think they have it all figured out tend to be hazardous to their companies.

Finally, pay attention to the tenor of their storytelling. Do they dwell on blaming external factors or other people? That suggests a lack of accountability. Do they gloss over the details? That points to shallow reflection. Mature CEOs own their failures and extract every ounce of available learning.

How do you foster innovation and creativity across the organization?

Switch gears to the CEO’s thoughts on catalyzing breakthrough ideas. Consider an opener like: “Innovation is so critical for staying ahead of the curve. What’s your approach to nurturing creativity and outside-the-box thinking on your teams?”

Reinvention is an imperative in today’s fast-changing business environment. Competitive advantages erode faster than ever as new players disrupt industries. A CEO’s ability to instill a spirit of innovation is key to their company’s long-term survival.

Some tactics to listen for:

Psychological safety. Do they work hard to create a culture where people feel comfortable respectfully challenging the status quo? Where dissent and debate around ideas is welcomed? That’s fertile soil for innovation.
Dedicated innovation time. Do they carve out space for employees to experiment with new concepts – through hack days, side projects, etc. Protecting people’s bandwidth encourages creative exploration.
Diverse and cross-functional teams. Research shows that diversity unlocks innovation by introducing more varied information and perspectives. Is this CEO thoughtful about assembling teams?

Rewards and recognition for innovative ideas. People do more of what is celebrated and recognized. Is innovation baked into performance evaluation and promotion decisions?
Opportunities to connect with customers. Great ideas often come from deeply understanding customer needs and frustrations. How much customer exposure do employees get?

Beware of innovation theater – visible markers like ping pong tables or blue sky offsites without deeper cultural DNA to support them. The most innovative companies make creativity a habit, not a rarity.

Also, note if the CEO seems energized by the topic. Are their eyes lighting up as they describe the crazy ideas their team has tried? Do they get animated recounting the twists and turns of bringing a new product to market? Passion for innovation starts at the top.

Phrase your follow-ups to invite specific examples. If they mention an initiative in passing, ask them to elaborate on how it came about and what early impact they’re seeing. Concrete details bring their philosophy to life.

In a world of constant disruption, a CEO’s stance toward innovation offers a window into the company’s capacity for reinvention. It’s perhaps the most future-leaning topic you can explore.

What do you think about building and maintaining a strong company culture?

Turn next to the CEO’s approach to crafting an exceptional organizational culture. Try a question like: “Company culture is so fundamental but hard to get right. How do you think about shaping and sustaining an awesome culture at [Company]?”

Culture is the bedrock of any thriving company – the set of shared values, norms, and behaviors that guide how work gets done. It’s the invisible hand directing employee actions when no one’s watching. And it has major bottom-line implications, with research linking healthy cultures to better financial performance, talent retention, and customer satisfaction.

A CEO’s role in culture-building is part strategist, part chief storyteller. Strong answers will cover:

Clarity of values. Have they distilled the culture down to a crisp, memorable set of core values? And relentlessly communicated them through words and actions? Cultural cohesion starts with a shared language.
Hiring and onboarding. Do they treat hiring as one of their most impactful levers? Are they ruthless about cultural fit, even at the expense of raw skills? Early employees mold the culture for years to come.
Rituals and traditions. From weekly all-hands to annual offsites, do they use rituals to reinforce cultural priorities? Smartly designed rituals create a consistent heartbeat.

Leading by example. Are they an authentic embodiment of the culture they preach? Employees watch the CEO’s every move for cues on what’s valued. Inconsistency breeds cynicism.
Storytelling and folklore. Do they spotlight employees who exemplify the culture, making them heroes? Those stories become organizational lore, handed down to new recruits. Vivid anecdotes beat vague slogans.
Adapting as the company scales. Adding people adds cultural complexity. Is the CEO intentional about evolving the culture to handle headcount growth? What worked for 50 won’t necessarily work for 500.

If their answers are generic or short on examples, probe deeper. Ask about a star employee who personifies the culture, or an underperformer whose values misalignment necessitated a tough conversation.

Also, listen to how they describe the culture to candidates or customers. Is the pitch consistent and compelling? When the going gets tough, a crystalline culture binds people together.

Finally, observe whether they seem to enjoy the culture-building part of their role. It’s as much an art as a science, demanding vision, emotional intelligence, and interpersonal dexterity. How a CEO approaches this squishy domain speaks volumes.

What is your strategy for attracting, developing, and retaining top talent?

People are any company’s most important asset. Dig into the CEO’s game plan with a question like: “Talent is so fundamental to executing your vision. How are you thinking about bringing in amazing people, helping them grow, and keeping them for the long haul?”

In a competitive labor market, human capital strategy is business strategy. A CEO’s philosophy and track record on talent will make or break their company’s trajectory. Their answer is a crucial indicator of how talent is truly prioritized and managed.

A few elements to listen for:

Employer branding. What’s their vision for how the company shows up in the talent marketplace? Is there a crisp employee value proposition and story that will resonate with A-players?
Recruiting machine. How are they building the recruiting muscle to consistently draw a deep candidate pool? It’s a grind – from job descriptions to interview loops to selling top prospects. There’s no silver bullet.
Onboarding and training. Once great people join, how are they set up for success? Careful onboarding, training, and mentorship in those pivotal early days can dramatically boost retention and performance.

Growth and development. How do they think about helping each employee reach their full potential? Are there ample opportunities for stretch assignments, skill-building, and advancement? Careers are a lattice, not a ladder.
Performance management. How do they evaluate and reward top contributors while respectfully parting ways with underperformers? Striking the right balance requires clear goals, frequent feedback, and a commitment to fairness.
Inclusion and belonging. In an era of remote and distributed work, how are they fostering an environment where every employee feels valued and able to do their best work? Proactive efforts to boost inclusion and psychological safety are key.

If the CEO seems to have a well-honed point of view, ask for a specific example that illustrates it in action. Maybe it’s a story of going above and beyond to land an exceptional hire or having a difficult conversation to coax the best out of a struggling manager.

Also, try to gauge how much time they’re spending on the nuts and bolts of people’s practices. Are they delegating talent completely to HR, or deeply engaged in hiring profiles, development plans, and compensation decisions? The best CEOs are relentless talent magnets and advocates.

Finally, observe whether they seem energized or drained by the topic. Managing talent is not for the faint of heart. It requires a CEO who intrinsically enjoys developing people and teams over the long arc of a career. How they embrace this duty is telling.

What keeps you up at night as a CEO?

This question cuts right to the heart of the CEO’s greatest worries and preoccupations. You might ask it like this: “When you wake up at 3am and can’t fall back asleep, what are the biggest concerns or challenges bouncing around your mind?”

There’s an unvarnished honesty that emerges in those moments of sleeplessness. It’s when the professional veneer fades and raw doubts and fears come to the surface. A CEO’s deepest anxieties offer a window into both their demons and their company’s most intractable problems.

Some common themes that might arise:

Existential threats to the business model – from new competitors to technological shifts to regulatory changes. CEOs are paid to spot gathering storms and mobilize the company before it’s too late.
Major execution risks for key initiatives. Big strategic bets have countless moving parts and unavoidable uncertainties. The CEO bears ultimate responsibility for their outcomes, and the mental burden can be immense.
Dynamics and decisions around their executive team. From thorny performance issues to looming departures to interpersonal tensions, managing a group of ambitious leaders is fraught with complexity.

Fundraising pressures and investor expectations. In venture-backed companies especially, CEOs grapple with the relentless treadmill of raising money and delivering against ever-rising growth targets.
Fiduciary duty and stakeholder obligations in the face of difficult tradeoffs. The buck stops with the CEO, and they’re held to an extremely high standard. Upholding corporate integrity while balancing shareholder interests is a heavy mantle.

Push on whatever fear they mention to understand both its practical implications and emotional contours. Strive to separate the chronic anxieties from the emergent crises, and take note of how long each worry seems to stay lodged in the CEO’s mind.

Also, pay attention to any physical tells as they answer. Do you notice a sudden change in body language – tensing shoulders or a furrowed brow? Those unfiltered reactions can say as much as their verbal response.

Finally, assess the CEO’s self-awareness about their stress and how they seek to manage or mitigate it. Do they lean on their team for support, or isolate themselves in a hero complex? Do they maintain habits outside work to replenish their energy, or resort to unhealthy numbing behaviors? The CEO sets the tone, and burnout is contagious.

Tell me about a time you had to make a high-stakes decision with limited information. How did you handle it?

Decision-making under uncertainty is a core part of the CEO job description. Probe their approach with an opener like: “Can you walk me through a situation where you had to make a hugely impactful choice without all the data you wanted? What was your thought process?”

In a fast-paced business environment, complete information is a luxury. More often, CEOs must make consequential judgment calls on partial data, relying on pattern recognition and calculated risk-taking. Their answer will illuminate how they grapple with ambiguity.

A strong response will likely cover a few key elements:

Quickly triaging the available information. What’s the most critical data we do have, and what would be nice to have but isn’t a true blocker? Ruthless prioritization matters in time-sensitive situations.

Deploying a team to gather intelligence. Who has relevant knowledge or expertise to tap? How can you set up parallel workstreams to learn faster? Brief, focused huddles can unlock crucial insights.
Pressure-testing assumptions and mental models. What might you be wrong about? Where are the weak spots in your reasoning? Cultivating a habit of self-challenge helps counter confirmation bias.
Consulting and learning from others while preserving independent judgment. Who has faced similar decisions in the past, and what lessons can you glean from them? Strong CEOs incorporate outside views while maintaining conviction.

Bounding the downside while preserving option value. What’s the worst-case scenario, and how can you cap that risk? Building in contingencies creates breathing room and flexibility.
Communicating the decision with humanity and transparency. How can you share context and rationale while acknowledging the uncertainty? Treating people as adults earns trust and buy-in for the path forward.

Throughout their answer, listen for signs of intellectual humility and resilience. Do they openly acknowledge what they don’t know or have doubts about? Are they willing to course-correct swiftly if new information emerges? Confident uncertainty is the sweet spot.

If they seem hesitant to share a specific example, gently explain that you’re not seeking to dissect the decision itself but rather to understand their approach. Most CEOs relish the chance to unpack their logic with an engaged thought partner.

Finally, observe whether they seem energized or unsettled by the memory of navigating ambiguity. Some CEOs thrive on the adrenaline, while others grit their teeth through it. There’s no universally right way, but self-awareness is key.

If you could go back and give your 25-year-old self one piece of career advice, what would it be and why?

Close the interview with a reflective, future-oriented question to reveal the CEO’s deepest lessons and insights. Try a framing like: “Imagine you could send a message back in time to yourself at the beginning of your career. What’s the single most important thing you’d want to say?”

This question invites the CEO to distill a lifetime of hard-won wisdom into a pithy, memorable soundbite. It requires both introspection about the defining moments of their journey and imagination about how that knowledge could alter a younger person’s trajectory.

Some evergreen advice you may hear:

Bet on yourself. Take risks, seize opportunities, and trust your ability to figure it out. So much success is stepping up to the plate and backing yourself.

Develop your communication skills. The higher you climb, the more your job is to inspire and galvanize others. Mastering public speaking, writing, and storytelling unlocks tremendous leverage.
Build a network before you need it. Relationships are the most important currency in business. Playing the long game and being generous with your time and expertise pays massive dividends.
Don’t optimize for salary early on. Prioritize learning, mentorship, and responsibility. Those early years are an investment in the rest of your career.

Embrace discomfort as a growth signal. The moments that challenge you most are the ones that mold you. Treat them as teachers and lean in.
Hire people smarter than you. Your job is to build an incredible team, not stroke your ego. Packing the roster with A-players makes everything easier.
Fire faster. Your instinct will be to avoid hard people decisions. Resist that temptation. Tolerating underperformance or bad behavior is toxic.

As they share their advice, probe around why it resonates so deeply. Is it a lesson they learned the hard way through a crucible moment? Is it something a key mentor told them that’s become a personal mantra? Dig for the origin story.

Also, observe their tone and emotional register as they impart wisdom. Do they seem to be speaking from a place of gratitude and humility, aware of their luck and help along the way? Or does it veer into self-aggrandizement about their unique talents? The framing hints at their character.

Finally, reflect to them a crisp summary of their advice, as you understand it. Check if you’ve captured the essence and give them a chance to clarify or expand. Mirroring their words shows you’ve listened intently.

As the interview wraps up, thank the CEO sincerely for their time and candor. Acknowledge that you’ve covered sensitive topics and that you’ll treat the conversation with discretion and care. If something they shared especially resonated, let them know.

Conclusion

Asking powerful questions is the key to a revealing CEO interview.

By covering these 10 essential topics, you’ll gain a richer, more nuanced understanding of the leader at the helm.

Remember that your goal is to see the world through their eyes – their hopes and fears, triumphs and failures, deepest beliefs, and most urgent priorities.

The more context you can elicit, the more accurately you can assess their fit for the challenge ahead.

Don’t shy away from the thorny stuff, but always probe with respect and empathy.

The CEO role is a lonely one, and many will welcome an opportunity to process its complexities with a curious, thoughtful partner.

How you show up in the conversation is as important as what you ask.

With practice and preparation, you’ll hone your ability to quickly build rapport, surface candid insights, and paint a vivid portrait of the CEO in front of you.

Mastering the art of the interview will serve you in countless professional situations, from hiring to partnering to pitching.

So get out there and start asking.

With the right questions as your guide, you’ll be amazed at what you discover – about others and yourself.

The most meaningful breakthroughs often start with genuine, courageous curiosity.