Best Question to ask a CEO

99 (Interesting) Questions to Ask a CEO & Executives

Best Question to ask a CEO

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.

If you ever, get such a chance, punce right at it. Put together relevant questions to ask a CEO so you don’t waste their time. In this blog, you learn about why it’s important to ask questions to CEOs and how to conduct the conversation.

We’ve also compiled a list of interesting questions to ask a CEO. Steal all you want. But first, let’s clear the motive behind asking questions to a CEO or executives.

Why must you ask questions to a CEO?

For a long time, company culture was dictated by C-suite executives. Employee sentiment takes a back seat. But now, the focus is shifting. Companies have started to consider employees’ opinions due to decreasing employee engagement and retention. IN US alone, 3 – 4 million employees are quitting jobs each month. Companies now conduct open conversations so employees can set expectations accordingly. 

CEOs and leaders no longer sit behind closed doors. They’re open to difficult questions as well as fun conversations. Grab this opportunity to interview various company leaders. Asking questions to a CEO or other executives in a company gives you an opportunity to deep dive into the company values —a direct reflection of the CEO’s values. 

Be ready with interesting questions during a town hall meeting, office hours virtual meeting, roundtable discussion, virtual event or an interview. He/she plays the key role in the growth, culture and development of the organization so they provide you maximum insights into the company. 

How can you make the interview successful?

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. Make the most it. 

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. 

  1. 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. 

  1. Ask specific 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. 

  1. Follow virtual 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. 

Strategic questions to ask senior leaders of your company

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. 

Let’s dive in.

Personal Interview questions to ask a cEO in an interview

  1. Why did you start this company?
  2. How did you go about researching and validating your idea for this company?
  3. Why did you join the position of a CEO?
  4. How did you get to this point in your career?
  5. Can you give some tips for youngsters who aspire to make it big like you?
  6. What are your personal goals?
  7. Do you have any hobbies outside of work that help become a better boss?
  8. Whom do you look up to for inspiration?
  9. What other companies do you admire in your industry?
  10. What’s the average number of meetings you take up in a single day?
  11. What according to you makes a great team?
  12. What was your most difficult career-related decision so far?

Best Questions to ask a CEO During an All-hands meeting

  1. What’s the biggest strength of your company?
  2. How does your product work? 
  3. What problems does your product solve?
  4. How did Covid affect your company?
  5. What are the biggest challenges your company is facing today?
  6. How do you plan to overcome these challenges?
  7. What process does your company follow to solve its problems?
  8. Is the company funded? If yes, how many rounds & how much funding, If No, then are you open to funding?
  9. What traits do you look for in a potential candidate for a job in your company?
  10. What qualities do you look for in your C-suite team?
  11. Where do you see your company in the next 5 years?
  12. Do you promote employees within the company?
  13. If you could, what would you like to change about your company?
  14. What would you do if your company’ supply chain is disrupted? (crisis questions)
  15. If you’re ever in dispute with the board of directors, how would you tilt them to your side?
  16. 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?

Work Culture Related Interview Questions

  1. What steps do you take for the welfare of your employees?
  2. Do you ever have clashes with your staff?
  3. What do you think is the more important aspect of a good company culture?
  4. Do you listen to the point of view of your employees?
  5. When was the last time you chatted with an employee one-on-one?
  6. How do you motivate your employees when they feel down?
  7. Do you tackle burnout in your company?
  8. What are your thoughts on working from home?
  9. How do you tackle the generation gap with your new and young hires?

Strategic Industry Questions to Ask Senior Leaders

  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?

Career Related Questions

  1. What courses did you take that helped you land the job as a CEO?
  2. Which job in your overall career contributed the most to build your expertise?
  3. Who do you suggest young aspirants to seek a career opportunity in this industry?
  4. What roles do you think are most lucrative in this industry?

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.

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