100 Questions To Ask a CEO (Feat. Real CEOs)
Lisa Ardill
Content Editor at Workvivo
1 Jan 2024
As a people leader, you have a close connection to the pulse of the employees at your business. You also have a more direct line to the C-suite than most of those employees.
It’s not uncommon for both sides to have concerns about engagement, communication, and company culture. However, there isn’t always a reliable mechanism to communicate and resolve these concerns.
We’ve compiled 100 good questions – including 30-plus that come straight from real CEOs themselves – that HR, internal comms, and engagement leaders like you can use. If you’re looking to facilitate a dialog with your CEO so you can better support the employees you serve, then these questions are for you.
What types of questions should you ask a CEO and why?
As a people leader, you have more access to the CEO than the average frontline employee. Still, when opportunities arise to ask your CEO a question, knowing what exactly to ask isn’t always easy.
It might help to start by thinking about the types or categories of questions that would make the most impact, including:
- Questions about company culture
- Questions about employee experience
- Questions about employee engagement
- Questions about recruiting and retaining talent
- Questions about digital transformation
- Questions about diversity, equity, inclusion, and belonging (DEIB)
- Questions about risk management
- Questions about long-term vision
- Questions about executive challenges
- Questions about market competition
- Questions about industry challenges
- Questions about crisis communication
- Questions about business ethics
- Questions about environmental, social, and corporate governance (ESG)
We’ll show you powerful examples in each of these categories. And stick around for the end, where we’ll reveal 30-plus CEOs' responses to “What is the best question to ask a CEO?”
Company culture questions to ask a CEO
Company culture is everything. It affects almost every element of a company, and employees and leaders alike feel it every single day.
But bridging the divide between executive leadership and the general workforce can sometimes be tough (without the right tools). And getting culture right in a digital-first environment can be tricky – especially for CEOs struggling to adapt to the new way of working.
Why should you ask a CEO about company culture? Because employees need to hear their vision for what the company should be. Only then can you construct feedback loops to reconcile what is with what should be.
Best company culture questions
- Why did you start this company (or why did you join it)?
- What about this company makes you the most proud?
- What is something you hope to see change at this company?
- What is your desired timeline for that change?
- What are the warning signs that a company culture isn’t what it should be?
- Is there another organization or internal department whose culture you would point to as a model?
Employee experience questions to ask a CEO
Employee experience relates closely to culture. But here, instead of evaluating how the organization feels to an employee, we’re thinking about the day-to-day experience. It’s a subtle but meaningful difference.
For example, the tech hire sitting around without a laptop to work on is learning about the company culture, but the employee experience is failing.
Work-life balance and the work environment also play heavily into the employee experience.
Improving understanding of the employee experience (encompassing all backgrounds, personality types, and communication styles) will contribute to better engagement and morale throughout the company.
Why should you ask a CEO about employee experience? Because, just like company culture, the employee experience is a major driver of morale, performance, and retention.
Thoughtful questions here can lead to improvements in leadership style and better outcomes all around.
Best employee experience questions
- What are the three best elements of the current employee experience?
- What weaknesses do you see in the current employee experience?
- What do you plan to do to improve the employee experience?
- How has the transition to remote or hybrid work changed the employee experience at the company?
- What changes do you envision to improve the employee experience in a remote-first world?
Employee engagement questions for CEOs and senior leaders
When engagement suffers, the work suffers. And when the work suffers, so does the company’s likelihood of success.
But keeping remote employees engaged isn’t always easy. While this isn’t directly the CEO’s responsibility, your CEO may have insights to share – if you ask the right questions.
Why should you ask a CEO about employee engagement? Doing so can be a good way to gauge your CEO’s understanding of the current company environment, and it can create a subtle emphasis that attention in this area is needed by the CEO.
Best employee engagement questions
- What is your plan for how upper management will communicate with the rest of the staff?
- What does employee engagement look like in our company?
- How would we know if employee engagement was strong or poor?
- How do you motivate people to give their best?
- How can we improve connectedness between employees and their peers (and with management)?
Important questions on recruiting and retaining talent
Recruiting and retaining talent is harder than ever, but it’s vital to ongoing success. Building a company culture and employee engagement is hard when the employee pool constantly changes.
Why should you ask a CEO about recruiting and retaining talent? Because the ship doesn’t sail (let alone win the race!) without a qualified crew.
Best recruitment and retention questions
- What attracts high-quality talent to this company?
- What makes an employee want to stay at this company?
- What ideas do you have for making our business a more attractive place for motivated talent to work?
- How can HR and the C-suite work together to make sure we attract and keep high performers?
- How do we improve communication in a way to aid in retention?
Digital transformation questions for executive leaders
Digital transformation can feel chaotic at times, but it’s also necessary for survival in most industries. The way we’ve always done it might still work. But does it still win?
Not when the competition is reinventing the way they do it (and embracing a new generation of powerful technology to do it faster and better).
Why should you ask a CEO about digital transformation? Because digital transformation is the key to survival in most business contexts. A CEO must have a plan for digital transformation (and be able to communicate that plan).
Best digital transformation questions
- What are the key elements of your vision for digital transformation?
- What is the role of leadership in pushing forward into digital transformation?
- How can we support, upskill, or reskill workers whose roles will be impacted by digital transformation?
- How will digital transformation affect roles, skills, and job functions in our company?
- How do you plan to combat resistance to change during digital transformation?
DEIB questions for leadership
Diversity, equity, inclusion, and belonging (DEIB) is a vital discipline for any company that wants to support the broadest possible workforce (and benefit from a wide-ranging and diverse knowledge base).
Why should you ask a CEO about DEIB? Because far too often, DEIB initiatives are stilted, awkward, or mechanical. Understanding how authentically a CEO is (or isn’t) committed to DEIB could inform your HR and internal comms approach.
Best DEIB questions
- Why is DEIB important to our organization?
- What steps will you take to go past diversity initiatives and push toward a place of true belonging for all?
- What gets in the way of minorities feeling a sense of inclusion and belonging here?
- As CEO, what is your role in promoting DEIB?
Risk management questions to ask a CEO
Risk management is one area where CEOs typically focus, so it should be easy to get clear and detailed responses here. Of course, thinking about risk management and executing it are two different things.
For example, careful questions on risk management (tied back to a better corporate intranet) could even be a way to get your executive leadership excited about improving internal comms.
Why should you ask a CEO about risk management? Because there must be a risk management plan. And if there is one, the CEO should lead the way in communicating and championing that plan.
Best risk management questions
The best questions here will vary depending on the nature of the risks in your industry, so feel free to adapt these as needed.
- What are the leading external sources of risk to our organization?
- What are the most important internal risks?
- What are your plans for reducing risk by improving internal ops?
- How can we align risk management policies across divisions?
- How is our business continuity plan communicated? How is it executed?
Questions to uncover an executive’s long-term vision
It’s possible to maintain the status quo without a clear, compelling long-term vision. But is it possible to thrive? The most successful executives have a clear long-term vision that aligns with the company's mission – and they communicate that vision to everyone.
Why should you ask a CEO about long-term vision? Because that’s what the board hired the CEO to do! Just like you need a crew to sail the ship, every ship needs its captain.
Best long-term vision questions
- Where do you envision the company in five years? Ten?
- What company goals do you have that can’t be executed within a year?
- How will this organization adjust to coming changes in our industry?
- What long-term goals do you hope to achieve during your tenure as CEO?
- What other companies and leaders do you look to as models or examples?
Strategic questions about executive challenges
Being an executive isn’t easy – otherwise, everyone would do it.
There are challenges inherent to the role, like staying on top of industry trends while also staying engaged with people at every level of the organization. The CEO must make many decisions as well, often without clear right or wrong answers.
Why should you ask a CEO about executive challenges? Because CEOs aren’t superheroes. They have challenges to overcome, both personal and professional. It’s helpful when a CEO knows this and is humble enough to admit the need for growth.
Best executive challenge questions
- What are some challenges you face as CEO?
- Do you see a solution to those challenges?
- What can we do to help address those challenges?
- How can technology help to solve executive challenges?
Questions to ask a CEO about market competition
No matter who you are, one of these two statements is almost certainly true about your organization:
Larger, more established brands have better reach and name recognition.
Newer, more agile startups have dexterity (and perhaps outside funding) that you can’t match.
Your organization faces market challenges. The only question is what they look like – and what you’re going to do about them.
Why should you ask a CEO about market competition? Because businesses don’t exist in a vacuum. It matters how well or poorly things are going – but what’s even more important is how they’re going compared to your top competitors.
Best market competition questions
- What are the three biggest threats from our top competitors in the market?
- What do you see as a competitive advantage we offer that others can’t?
- How can we develop new advantages over the competition?
- Do you envision new AI tools providing us with a boost in competitiveness?
- Do you envision new AI tools as a threat (because competitors are in a better place to use them)?
Key questions to ask executives regarding industry challenges
What’s happening in your industry matters. A lot.
Many of the questions we’ve covered so far didn’t matter all that much for auto companies in 2008 or real estate investors in 2009. Their industries were in freefall, and executive leadership needed to draw on a different set of skills to overcome industry-wide challenges.
Why should you ask a CEO about industry challenges? Because if you’re not encountering any now, you will soon. It’s helpful to know a CEO’s mindset or perspective on current or future challenges.
Best industry challenge questions
- What do you see as the biggest threats to our industry as a whole?
- How can we position ourselves better than the competition as we face those challenges?
- What developing technologies could challenge our industry in the next three to five years?
- What developing technologies can we use to disrupt our industry in the next one to three years?
Crisis communication questions to ask a CEO
‘Crisis’ isn’t exactly a positive word, but if you stay in business long enough, one is inevitable on some level. Those industry crashes we referenced just above certainly qualify. Other crises include natural disasters, cyberattacks, and economic turbulence.
Why should you ask a CEO about crisis communication? Because if the crisis communication plan isn’t clear to HR, it’s likely not clear to anyone. Understanding the CEO’s vision and plan for execution during a crisis is vital.
Best crisis communication plan questions
- What would you do if our supply chain suffered a severe disruption?
- What would your first five actions be in the event of a natural disaster or other crisis of similar magnitude?
- How can we measure the effectiveness of our crisis communication plan before needing to use it?
- What do you envision as the distinction between the CEO’s and HR’s role during crisis communications?
- Do we have an effective platform or plan in place to distribute crisis communications?
Questions on business ethics for corporate leaders
Generally speaking, employees want to know they’re working for a business that will do the right thing, but sometimes the ‘right’ thing is subjective. Questions about business ethics can give you deeper insight into your CEO’s approach to ethical decision-making.
Why should you ask a CEO about business ethics? Executives set the ethical tone for any business. They should be able to speak directly and honestly about the organization’s approach to business ethics.
Best business ethics questions
- What is your guide for defining business ethics?
- How does leadership set the tone for an organization’s business ethics?
- How should employees go about reporting suspected unethical behavior?
- How can leadership influence people at all levels of the organization toward ethical decision-making?
ESG questions for C-level executives
Environmental, social, and governance (ESG) is a way of evaluating a company, often in an investing context. Asking a CEO how a company addresses concerns related to ESG can reveal a great deal about the CEO’s sense of vision and urgency on the topic.
Why should you ask a CEO about ESG? Because people, not just investors, care about an organization’s effect on society and the planet. By surfacing a CEO’s approach to this area, you’ll help to instill greater confidence in the company’s vision and impact.
Best ESG questions
- How do we prioritize ESG in our day-to-day operations?
- What are some specific environmental initiatives you plan to roll out in the next five years?
- How do you envision prioritizing ESG throughout the organization, not just at the stakeholder, board, or investor levels?
- What is the CEO’s role in promoting an ESG mentality throughout the company?
BONUS: The best questions to ask a CEO – according to 30-plus CEOs
Next up, we’ve got some powerful bonus content for you. We set out to answer a vital question: If given the chance, what questions should employees (including leaders) ask their CEO?
Over 30 CEOs were kind enough to give us their valuable insights. Many of them are CEOs of INC 500 companies who took time out of their busy schedules to help us answer: “What is the best question to ask a CEO?”
“What is the best question you’ve been asked as a CEO?”
Their responses ranged from their biggest challenges and personal and business values to questions about their character, employee career development, and company culture.
We’ve divided the CEOs’ responses into five categories. So read on for some of the best questions to ask a CEO and personal insights into what’s important to senior management.
Questions about culture
Culture in any organization comes from the top. So, it makes sense to jump straight to the top to learn more about a company’s culture.
These are the top questions CEOs shared that employees can ask to gain clarity about a company’s culture.
- Why do you personally care about embedding inclusion and belonging in our culture? (Godard Abel, CEO of G2.com)
- What is most important to your organization – mission, vision, or values? (Dennis Fois, CEO of Copper)
- What’s more important – using the company technology to make money or using the company technology to save lives? (Kevin Lustig, CEO of Scientist.com)
Questions about evaluation & career growth
It’s natural for any driven employee to wonder about an organization’s approach to evaluation and career development.
These questions might not make sense for a massive company town hall, but they could be really powerful when asked through a corporate communication platform like Workvivo.
Request your demo today to see how Workvivo makes it easier for executives to connect with employees at all levels.
- How is my success measured? (James Pelton, CEO of Mobile Text Alerts)
- My career goals are x, y, and z. How can I better help the company reach its goals while progressing in my career goals at the same time? (Trey Gibson, CEO of SPOTIO)
- What are my strengths, and how do you see me nurturing them to fit into an irreplaceable role in the company? (Nikhil Choudhary, CEO of Zenith Engineers Inc)
- What do I need to get better at so I can run my own company someday? (Chris Kelly, CEO of NextGen Leads)
- How can I learn more and better contribute to the company? (Jolina Li, CEO of BuzzyBooth)
- What do I need to start learning and doing now to have your job in a few years? (Andrew McConnell, CEO of Rented.com)
- What do I need to do to align my actions with your interests? (Alexander Kesler, CEO of INFUSEmedia)
- How can I make sure I’m adding value to the organization? (Michael Stratta, CEO of Arcalea)
- What is the number one aspect that you look for as a trait in all your employees when bringing them onto the team? (Anubh Shah, CEO of With Clarity)
- Why did you hire me? (Kyle Goguen, CEO of Pawstruck)
- What is the ONE business challenge I can solve that would make the single biggest impact on the organization? (Michael Mogill, CEO of Crisp Video)
- How can we automate my job function to make the process more efficient? (Jason Hennessey, CEO of Hennessy Digital)
- What can I do in my day-to-day role to better align with the company vision? (Jamie Hall, CEO of Arsenal Strength)
- What new skill can I learn? (Taylor Ryan, CEO of ArchitectureQuote.com)
Questions about company success
Being at the helm of an organization can be an exhilarating, daunting, and sometimes lonely place. The success (or otherwise) of the business ultimately lies with the CEO.
These are questions high-performing CEOs recommend asking to get insight into a CEO’s approach to the company’s long-term success.
- What are you most afraid of regarding the future success of the business? (Debbie Madden, CEO of Stride Consulting)
- Where is the company today versus where you thought it would have been five years ago? (Bobby Gill, CEO of Blue Label Labs)
- How are we sure we’ll always win as the industry changes? (Loren Brill, CEO of Sweet Loren’s)
- Will we run out of cash? (Loren Burnett, CEO of Qwinix Technologies )
Questions about values
As with culture, the values of any business will ultimately come from leadership. Smart questions about business values will help pull out clarifying information about what kind of leader a CEO is – and what kind of values that CEO holds.
- Have you ever made a negative impact on someone? [The manner in which a leader answers this question reflects the character of the leader, including their integrity and empathy, among other critical values.] (Gassia Gerges, 1Link Technology)
- When was the last time you changed your mind about something important? (Max Rice, CEO of Skyverge)
- When and how will you know if you’re not the most qualified person to be running the company as it continues to grow and scale? (Casey Clark, CEO of Cultivate Advisors)
- What would your staff say is your management style? (Tyler Covey, CEO of MDstaffers)
- As a CEO, your job is to make sure that the necessary tools are there to allow us, the employees, to focus on the task. How do you handle any external factors that you cannot control but affect the business? What do you do to prevent yourself from over- or under-reacting? (Cindy Lee, CEO of LYNC Logistics)
Personal questions
The CEOs we interviewed gave some fascinating responses about their favorite personal questions they’d received from employees.
- How are you doing? [With the intention of wanting to truly help or lighten burdens.] (Weston Lunsford, CEO of Dental Intelligence)
- “The most impressive question ever asked of me was by an intern. It was simply, ‘why?’ She had the guts to question a decision I made, and it stuck with me over the years as a symbol that no one is above logic.” (Joe Hessling, CEO of 365 Retail Markets )
- How can I help you? (Jimmy Kim, CEO of Sendlane)
- How are you? (Jordi Torras, CEO of Inbenta)
- How are you doing? [Asked in a helpful way that recognizes that the CEO is human and has worries and pressures like everybody else – possibly more!] (John Goulding, CEO of Workvivo)
- Knowing what you know now, would you hire yourself for your job? (Shawn Lipman, CEO of Feedonomics)
- If you had one do-over in the last three years, what would you do over? (Henry Schuck, CEO of ZoomInfo)
- What are your personal goals? (Seth Goldman, CEO of UrbanStems)
Workvivo helps CEOs build a community of culture and communication
Getting company culture right takes effort. It takes the right mindset from executive leadership and the right initiative to execute their vision. But it takes the right direction and guidance from people leadership to get them there – and the right tools to do it!
Workvivo is the tool people leaders need to lay the foundation for better culture and communication – whether your workplace is remote or hybrid. It’s the employee engagement platform built for how your teams work, with social intranet features that give leadership teams access to the thoughts and perspectives of the entire company for a better understanding of where people are coming from.
With more direct channels of communication (even one-on-one), executives can express a genuine interest in (and follow up with) teams and employees. It’s a great first step toward building the community you want to work with.
Ready to get started? Book your Workvivo demo now!
