99+ (Interesting) Questions to Ask a CEO & Executives in 2023

Asking questions to a CEO, company leader or any C-suite executive is a rare opportunity. A short discussion or interview with leaders can inspire you to stive for greatness in life. Anybody who’s sitting in the top position is bound to have interesting takes on different aspect of life be it career, company or industries in general.

Since the company leaders are open to conversations, it’s your responsibility to keep them interested. Getting a chance to interact with a CEO or other C-suite officers is rare.

It is also critical to ensure that you do not ignore the audience if they are physically present at the venue. Be sure to allocate time at the end of the conversation to address any audience questions, either those that were submitted earlier or through the mobile event app. By doing so, you can create a more inclusive and engaging experience for everyone involved.

Keep the below pointers in mind while asking questions to a CEO or a leader in an organization:

1. It’s Not A FUN ‘Ask Me Anything’

Even though your CEO has agreed for an ‘ask me anything’, it doesn’t mean you’ll fire off all candid questions. Remember you’re talking to a company leader. Maintain the decorum of the conversation/interview. Ask relevant questions so the conversation becomes enjoyable for you both. 

2. Show Genuine Interest 

It’s a rare opportunity to get a chance to talk to an organization’s leaders. Don’t think of it as a task. Show genuine interest in the conversation. Indeed recommends beginning the conversation with a compliment to the CEO or asking a question that interests them. These tricks let you portray a genuine interest that leads to a healthy conversation. 

3. Be Specific With Your Questions 

Generic questions like, “where did you grow up” or “what are your hobbies” are out of fashion. Specific questions related to executives’ personal life, industry or company captures the person’s interest in the conversation. It gets their brain rolling as they think of answers which makes the conversation more engaging to both the speaker and listeners. 

4. Follow Meeting Etiquettes 

If you find yourself in a virtual meeting, don’t hesitate. In a hybrid work environment it’s natural that the company conducts virtual Q/As and interviews. Follow virtual etiquettes like dressing up well for the call and keeping the background clean to maintain professionalism during the conversation. 

Given the chance, what questions would you ask a CEO or another executive leader? You sure can’t ask them unnecessary questions. It wastes their time and you create a bad impression. We’ve compiled a list of 99+ good questions to ask leaders in your company. Now you can dive straight into the conversation without spending hours on gazillion websites, looking for questions. 

1. Why did you choose to get into this industry?
2. Who do you think are your top competitors in the industry?
3. What’s the USP of your company that separates you from your competitors?
4. What changes would you like to bring into the industry?
5. How do you think the industry will change in the coming years?
6. What are some of the boons of this industry?
7. What are some of the banes of this industry?
8. Would the crypto revolution affect this industry?
9. What new ideas in the industry excite you?
10. How does your product work? 
11. What problems does your product solve?
12. What process does your company follow to solve its problems?
13. Is the company funded? If yes, how many rounds & how much funding, If No, then are you open to funding?
14. What traits do you look for in a potential candidate for a job in your company?
15. What qualities do you look for in your C-suite team?
16. If you’re ever in dispute with the board of directors, how would you tilt them to your side?
17. How did you grow your company when you had just 0 users? Which channels/ tools/strategies worked the most for acquiring the first 100 users?
18. What’s the best way of communicating within the organization according to you?
19. What do you do to retain employees?
20. What’s your process for promoting employees within your company?
21. If you could change one thing about the company’s system right now, what would it be?
22. What would you do if you were given $10,000 to improve the structure of your company?
23. Which competitor CEO is your favorite?
24. What do you think sets our company apart from others in the same field?
25. What are your goals for the company in the next 5 years?

26. Why did you start this company?
27. How did you go about researching and validating your idea for this company?
28. Why did you join the position of a CEO?
29. How did you get to this point in your career?
30. Can you give some tips for youngsters who aspire to make it big like you?
31. What are your personal goals?
32. Do you have any hobbies outside of work that help become a better boss?
33. Whom do you look up to for inspiration?
34. What other companies do you admire in your industry?
35. What’s the average number of meetings you take up in a single day?
36. What according to you makes a great team?
37. What was your most difficult career-related decision so far?
38. What inspired you to take up this path in life?
39. What is the most important skill a CEO must have?
40. How did you grow into your role as a CEO?
41. What is the best advice that someone has ever given you?
42. Were you always sure of this career path? If not, what did you want to do instead?
43. What was your first goal when you joined the company as a CEO?
44. How do you handle negative feedback from the board of directors or financial advisors?
45. If you could, what other industries would you like to partake in?
46. What’s the latest technology that you think can change your industry?
47. When you started, what was the position of the company in your industry?
48. Do you think Artificial Intelligence (AI) can take jobs in your industry?
49. Would you ever substitute employees with AI? If yes, in what positions would you make the change? 
50. Do you think there’s a place for new startups in this industry?
51. Would prefer industrial talks with a new businessman or an experienced C-suite officer?
52. How do you stay motivated and focused on goals?
53. How do you stay informed about industry trends and developments?

54. What’s the biggest strength of your company?
55. How did Covid affect your company?
56. What are the biggest challenges your company is facing today?
57. How do you plan to overcome these challenges?
58. What process does your company follow to solve its problems?
59. Is the company funded? If yes, how many rounds & how much funding, If No, then are you open to funding?
60. What traits do you look for in a potential candidate for a job in your company?
61. What qualities do you look for in your C-suite team?
62. Where do you see your company in the next 5 years?
63. Do you promote employees within the company?
64. If you could, what would you like to change about your company?
65. What would you do if your company’ supply chain is disrupted? (crisis questions)
66. If you’re ever in dispute with the board of directors, how would you tilt them to your side?
67. How did you grow your company when you had just 0 users? Which channels/ tools/strategies worked the most for acquiring the first 100 users?
68. What steps do you take for the welfare of your employees?
69. Do you ever have clashes with your staff?
70. What do you think is the more important aspect of a good company culture?
71. Do you listen to the point of view of your employees?
72. When was the last time you chatted with an employee one-on-one?
73. Do you tackle burnout in your company?
74. What are your thoughts on working from home?
75. Would you like to work from home as a CEO?

76. What has been your favorite project so far?
77. If you could trade places with anyone for a day, who would it be and why?
78. What’s the most adventurous thing you’ve ever done?
79. If you could be a superhero, would it be?
80. If you could have dinner with any nobel prize winner, who would it be?
81. What book have you read recently?
82. What’s your goto food when you are running short of time ? 
83. What’s the most memorable vacation you’ve ever taken?
84. What’s the best concert or music festival you’ve ever been to?
85. What’s your favorite hobby or pastime?
86. If you could live anywhere in the world, where would it be?
87. What’s your favorite movie or TV show?
88. If you could have any animal as a pet, what would it be?
89. What’s your favorite sports team?
90. If you could only listen to one song for the rest of your life, what would it be?
91. Which is your favorite newcomer in the industry who has made it big?
92. Who was your inspiration as a kid?
93. What do you consider to be your greatest achievement as CEO?
94. What is the last time you had to think outside of the box ?
95. What is something you wish you had known before becoming CEO?

96. How do you tackle the generation gap with your new and young hires?
97. How do you motivate your employees when they feel down?
98. What tips would you give to an interviewee who wants to get hired in this company?
99. Have you ever laid someone off? 
100. What’s the most possible reason for big layoffs from your company?
101. How does your company allow employees to advance their careers?
102. Who is the most inspiring employee that you’ve ever come across? What inspired you about them?
103. How do you measure the efficiency of your HR department?
104. Can you describe the company’s approach to marketing and communications?
105. If you were given a $10,000 marketing budget, what would you do with it?
106. If you could take anybody to advertise your company, which celebrity would you reach out to?
107. Do you give a pep talk to your sales team?
108. How do you define employee engagement?
109. What do you do to promote employee engagement in your company?
110. What do you do to make employees feel valued at work?
111. Do you think companies should focus on employee happiness at work?

112. What courses did you take that helped you land the job as a CEO?
113. Which job in your overall career contributed the most to building your expertise?
114. Do you think there are opportunities for young aspirants in this industry?
115. What roles do you think are most lucrative in this industry?
116. What training and resources are available out there to help one succeed as a CEO?
117. What should a person do to get into a leadership position in a company?
118. How does a person get promoted faster if they want to end up as a young CEO?
119. How should a present employee in this company enhance their skill set if they want to become the CEO?
120. Were you a brilliant student in school? 
121. How do you think an academically average student should pursue leadership roles like CEO?
122. What was your specialization in college?
123. How did your specialization help you shape your career?
124. What’s your preferred path to take after graduating to end up as a CEO like you?
125. What is the most common mistake you see students making these days that hamper their careers?
126. Are you happy with your career choices?

Use Best Questions to Ask Leaders

Remember to make the most any discussion with a CEO or another executive. Use questions from the list above to make the conversation interesting for the speaker and yourself. These questions will lighten the mood of the everyone in the room and you’ll get some interesting answers that inspire you.