By Pete Rawlinson.

Ever wondered what your CEO is thinking?

Do you ever think about the questions you would like to ask them?

Maybe you’ve pondered the questions a CEO would actually like to be asked by their employees?

Or you’ve tried to guess what the absolute best question to ask a CEO is.

Internal communication and employee engagement are obviously very important to us at Workvivo and we believe that communication is key for any organisation to be successful.

We also believe that communication should be open, from the top to the bottom of the organization.

With this in mind, we reached out to some of the world’s leading CEO’s and asked them to share some of the best, most impressive and challenging questions they’ve been asked by their employees in the past.

Over 30 CEO’s were kind enough to take part, many of them are CEO’s of INC 500 companies, who took time out of their busy schedules to help us answer the question “What is the best question to ask a CEO?”

The responses we received ranged from personal and business values, to questions about their character, what they think of their employees career development and company culture. We had some really interesting replies.

Read below to tap into the mindset of the top decision maker – you’ll learn some of the best questions they’ve been asked on current and future strategy, questions about their motivations, questions about their vision and if you’re lucky, the questions to ask that will help you gain personal insights into what to ask your own CEO about their intent for the business.

Let your digital communications become your competitive advantage. Download our latest book “The Digital Communications Landscape: Getting it Right” here. 

Questions to Ask A CEO About Culture

Culture can mean many things to many people, but one thing is very clear when it comes to culture in any organisation.

It comes from the top.

See what impressed the CEO’s when it comes to questions on this vitally important topic.

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 To Ask A CEO About Evaluation & Career Growth

We received a lot of feedback from the CEOs who took part on career growth and development.

The means by which employees are being measured is a hotly-debated topic today.

From annual reviews to continuous assessment, the format and nature of feedback can enthuse or disengage an employee.

Here you’ll learn the questions that stood out the most to the CEO’s, on the subject of career growth.

Watch our recorded virtual event “Exploring the Psychology of Remote Working” here

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

nikhil choudhary ceo questions image

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, 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

Taylor Ryan's best CEO question

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.

Let your digital communications become your competitive advantage. Download our latest book “The Digital Communications Landscape: Getting it Right” here.

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 was some really interesting questions from the CEOs from a personal perspective.

It’s all too often forgotten that CEOs are people too and several of our responses came from this perspective

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?

Watch our recorded virtual event “Exploring the Psychology of Remote Working” here


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 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 Own Values

As with culture, the values of any business will ultimately come from the top.

Employees will tend to emulate the values of the CEO, so it’s important that a CEO’s values are clear and well-understood.

Lakshmi Srinivasan, CEO of Lakarya

What is your mindset that you carry while developing our company?

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?


The Digital Communication Landscape: Getting It Right