Updated 20 May 2022

What to look out for if you’re part of the hiring process or speaking to new employees.

The questions that an interviewee asks are a great indication of whether they’re a fit for your company culture. Here, we ask CEOs some of the most impactful questions they’ve heard and explore why smart questions like these might mean you’ve found your next new hire.

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Why Listening to Employees Is Important

The best leaders take a genuine interest in employee engagement and keep communication open. An employee engagement tool like Workvivo allows senior leaders to keep track of the team conversation. A key part of running a successful venture is retaining good staff and ensuring that they feel happy and motivated. Keeping the conversation alive and making employees feel listened to can help with these things.

Speak to the Workvivo team about how we can improve employee engagement for your business.

Who We Asked

Over 30 CEOs were kind enough to give us their valuable insights. Many of them are CEOs of INC 500 companies, taking time out of their busy schedules to help us answer the question “What is the best question to ask a CEO?”

What Were the Best Questions Asked?

Our responses ranged from their biggest challenges, personal and business values to questions about their character, employee career development, and company culture. 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

It’s very clear that when it comes to culture in any organisation, it comes from the top. If your candidate comes armed with CEO interview questions about your company culture, be careful to watch their reactions as you answer. Ask what the culture was like in the interviewee’s former company to discover whether this candidate will fit well with the rest of the team. Here are some of our favourite CEO interview questions about culture. Godard Abel, CEO of G2.com Why do you personally care about embedding inclusion and belonging in our culture? Dennis Fois, CEO of Copper What is most important to your organization—mission, vision or values?
Kevin Lustig, CEO of Scientist.com What’s more important – using the company technology to make money or using the company technology to save lives?

Questions about Evaluation & Career Growth

The CEO’s and their executive team received a lot of great questions about career growth. Having the CEO’s undivided attention is an opportunity for any candidate to make a great impression. Questions about growth show that they want to contribute to the company’s success, whether they’re interviewing or as a new hire. From annual reviews to continuous assessments, the format and nature of feedback can enthuse or disengage an employee and is a big challenge for upper management.

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James Pelton, CEO of Mobile Text Alerts How is my success measured?
Trey Gibson, CEO of SPOTIO 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? Nikhil Choudhary, CEO of Zenith Engineers Inc What are my strengths and how do you see me nurturing them to fit into an irreplaceable role in the company
Chris Kelly, CEO of NextGen Leads What do I need to get better at so I can run my own company someday? Jolina Li, CEO of BuzzyBooth How can I learn more and better contribute to the company? Andrew McConnell, CEO of Rented.com What do I need to start learning and doing now to have your job in a few years? Alexander Kesler, CEO of INFUSEmedia What do I need to do to align my actions with your interests? Michael Stratta, CEO of Arcalea How can I make sure I’m adding value to the organization? Anubh Shah, CEO of With Clarity What is the number 1 aspect that you look for as a trait in all your employees when bringing them onto the team? Kyle Goguen, CEO of Pawstruck Why did you hire me? Michael Mogill, CEO of Crisp Video What is the ONE business challenge I can solve that would make the single biggest impact on the organization? Jason Hennessey, CEO of Hennessey Digital How can we automate my job function to make the process more efficient? Jamie Hall, CEO of Arsenal Strength What can I do in my day to day role to better align with the company vision? Taylor Ryan, CEO of ArchitectureQuote.com What new skill can I learn?

Questions to Ask a CEO About Company Success

Being at the helm of an organisation can be an exhilarating, daunting and sometimes lonely place. The success or otherwise of the business ultimately lies with the CEO.

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If a candidate or new hire asks about company success, it’s a great sign that they want to contribute to it and expect to see themselves with the business long term. Let’s see what the CEOs were asked about company success that stuck with them until now. Debbie Madden, CEO of Stride Consulting What are you most afraid of regarding the future success of the business? Bobby Gill, CEO of Blue Label Labs Where is the company today versus where you thought it would have been 5 years ago? Loren Brill, CEO of Sweet Loren’s How are we sure we’ll always win as the industry changes? Loren Burnett, CEO of Qwinix Technologies Will we run out of cash?

Personal Questions To Ask A CEO

There were some really fascinating questions from the CEOs from a personal perspective. These employees remember that CEOs are human beings, after all, and take an interest in their valuable business knowledge and in their opinions as people. Questions of this sort can point to an insightful, caring individual, which is an important part of any company culture. Weston Lunsford, CEO of Dental Intelligence How are you doing? With the intention of wanting to truly help or lighten burdens. Joe Hessling, CEO of 365 Retail Markets 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. Jimmy Kim, CEO of Sendlane How can I help you?

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Jordi Torras, CEO of Inbenta How are you? John Goulding, CEO of Workvivo How are you doing? (Asked in a helpful way that recognizes that the CEO is human and has worries & pressures like everybody else – possibly more!) Shawn Lipman, CEO of Feedonomics Knowing what you know now, would you hire yourself for your job? Henry Schuck, CEO of ZoomInfo If you had one do-over in the last three years, what would you do over? Seth Goldman, CEO of UrbanStems “What are your personal goals?” In framing it that way, the employee was asking not just what my goals were for the business but how they aligned with my own expectations and values and, in turn, their own. This question often gets asked by an interviewee or new employee, but rarely does it get asked by an employee to their boss.

Great Questions to Ask a CEO about Their Values

As with culture, the values of any business will ultimately come from leadership. Smart questions about values will show the employee a little more about whether you’re a good leader, and the type of question they ask will also tell you what to expect from them in the future. For example, employees asking whether you have a hands-on approach to people management may be interested in how you’ll support them or might prefer to take a more autonomous role. Questions like these present an opportunity to dig into this more with them. Employees will tend to emulate the values of the CEO, so a CEO’s values must be clear and well-understood. Gassia Gerges, 1Link Technology “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 his/her integrity and empathy, among other critical values. Max Rice, CEO of Skyverge When was the last time you changed your mind about something important? Casey Clark, CEO of Cultivate Advisors 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? Tyler Covey, CEO of MDstaffers What would your staff say is your management style? Cindy Lee, CEO of LYNC Logistics 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? If you’re a CEO or senior leader interested in what your team is thinking, then an employee engagement platform is a great tool to improve your company culture. Want to know more? Book a demo with one of our employee engagement experts. Read more about employee communication in our free guide, The Digital Communication Landscape. New call-to-action