Questions to Ask a Potential CEO

Insight from Rameel Sheikh

You will get wooed during the interview process to be an operational leader. All (great) CEOs are amazing recruiters.

What you need to figure out is if you believe in this person.

Do you believe this person can lead you and your team every day?

No company is successful with a CEO who can’t get everyone on the same page, who can’t hire well, and who can’t chart out a vision.

Early in my career, I remember interviewing at one of my first jobs, and it was hard to tell if a leader was “good” or not.

After years of experimentation, I do the following to determine if someone is the real deal.

First ask these 3 questions to see if there is a potential match:

1. "Can you share instances where you've had to soften the message or withhold full truth from your team?"

   The way a CEO responds to this question can tell you a lot. Being the CEO will naturally cause you to withhold information from their team.
   
   If a CEO makes light of the question or suggests it's a common practice instead of an example, it may show a tendency to mislead employees frequently.
   
   Ideally, you're seeking a CEO who can openly discuss times when they've had to be less than fully transparent while balancing morale.
   

2. “What do you think is your greatest leadership blindspot?”

   This question is a fresh spin on the familiar "What's your greatest weakness?" but it goes deeper by focusing on blind spots—areas the CEO might not always notice or acknowledge.
   
   Their response will offer insights into their level of self-awareness. If the CEO struggles to provide a clear answer, it shows a lack of introspection. However, if they offer a thoughtful response, it shows a level of humility that's valuable in a leader.
   

3. “What would an employee who’s left the company say it’s like to work for you?”

   This inquiry is pivotal as it sheds light on the CEO's awareness of their impact and openness to acknowledge past leadership mistakes. If you can, get references when you are asking this question.

If you’re hesitant to pose probing questions for fear of offending the CEO, consider this is a red flag. Truly effective leaders appreciate and encourage tough questions.

If anything, asking these questions should make you look better in their eyes. Asking the tough questions before joining shows that you value your own time.

Once you've asked these questions, you must reach out to past employees who have worked with the CEO.

Try asking similar questions you've asked the CEO to see if they match. While not all former employees will be positive, this will reveal a ton about the CEO and culture of the company.