5 best questions to ask a CEO

5 best questions to ask a CEO

You’ve got a CEO in front of you, all ears, awaiting your question.

It's an opportunity to find out a nugget of information that potentially took them years to learn! So...

What should you ask them?!

A lot depends on context. For example… are they your CEO? Or just a CEO? We’ll touch on the first one, but the second - well, what if this is the CEO of your dream workplace? Or a start-up that you admire? With just moments to tap into the knowledge and experiences that got them to where they are, how can you make best use of that time?

Some of the big brains in the Pip Club community answered this very question. Next time you get the opportunity to ask a CEO a question, try one of their suggestions on for size!

5 best questions to ask your CEO

A quick skim of the internet will throw up tonnes of ‘questions to ask your CEO’, mostly along the following lines:

  1. What is the biggest challenge the organisation is facing at the moment?
  2. What are you most proud of at this organisation?
  3. What are your goals for the company over the next one/five years?
  4. What do you think are the most important traits in your senior leadership team?
  5. What’s the most exciting development in our industry at the moment?

They are very functional and genuinely insightful. The answers themselves could really help you understand your place in the big picture, especially if you’re new to the company.


If you want something a little more exciting, ask them one of the following questions instead.

5 best questions to ask a CEO

First things first: some context. Tom Kerwin wanted a lot of background information before considering this question. He asked whether they are a CEO & Founder, or a CEO that’s been hired to maintain a successful organisation without rocking the boat. You could learn a lot from either, but the lessons will be very different!

He also asked if they are likely to define ‘success’ in a way that is close enough to your own values to teach you much at all. Prior to asking these questions, consider how you might tweak the language to get you the answers you want. For example, in questions about ‘success’ - be clear about the type of success you want to hear about.

No need to worry about that for the first question though, as it takes care of itself!

1. How would you define a successful week/month/year?

This is an absolutely fascinating question to ask a CEO (thank you, Ece Kurtaraner). The possibilities are endless, but many will fall into the following categories:

  • User centric - anything to do with customer satisfaction is the hallmark of a CEO who is deeply invested in solving their customers’ problems.
  • Numerical - sales, revenue, growth. These indicate someone who puts commercial aspects of the role above all else (which can - should - mean prioritising users, of course).
  • Personal - for example, anything to do with happiness and wellbeing, either their own or that of their employees and users.

Or you can cut it back to “How do you define success?”. It seems like a simple enough question, but it’s a little peek inside their head - what’s most important to them, and where they likely spend most of their energy.

2. How do you decide when to trust your gut, and when to do more research and analysis?

This one is from Joel Stein. This is such a great question to ask; the internet is heaving with articles and experts that either tell you to go with your gut and stop getting lost in the numbers, or to do more research instead of following hunches.

Where does this CEO draw that line? Do they have a process for it, or is it in itself a gut feeling? And before asking this question, think about the answer yourself: when is the research you have done ‘enough’? Then see how their answer differs, and if you can learn something from it.

3. If you were starting from scratch, with your knowledge, but without your network or any of your wealth, how would you spend your first month and first $100?

Tom Kerwin suggested this gem. It's a great question to get them thinking and to find out what, with their experience, they would prioritise when starting a new business. And it’s way more interesting than asking “What would you prioritise when starting a new business?”.

Similarly, Charles Burdett suggested asking “What advice would you give yourself as you were first starting out as a CEO?”. Answers to this one could provide an interesting insight into the biggest obstacles they have overcome, or things that have surprised them.

4. How much have skill and luck proportionally contributed to your success?

Ben Mosior and Tom both came up with a variation on this theme - Tom suggested including 'timing' and 'connections' alongside skill and luck, too. If you’ve got time, go for it!

A tale about a person working hard and doing well is fine, but add in a dash of serendipity or an interesting side-plot and that’s a real story.

Rarely do success stories come about due to hard work alone. Luck often plays a part, and it’s good to be reminded of that, especially when you’re working hard but not yet a CEO (if that’s your goal!).

5. What excites you?

Jacob Welby suggested this question, perhaps including prompts such as ‘a new piece of tech, product or news’ - this is important if you’re looking for the next big thing to research!

But if you want to know more about the person, rather than the CEO, you could try: “What excites you, both in and out of work?”.

Either way, asking people to speak about something they are passionate about is very effective at getting them to drop their guard a little and loosen up.

Sharing enthusiasm with someone also creates a positive connection. The act of asking this question could be just as powerful as the answer you receive!

Bonus questions to ask a CEO

Okay, you’ve got a shot at another question! Try these:
  • Which forms of process have you found most and least useful?
  • What personality traits do you think are important in a successful CEO?
  • Do you think you could reach the same level of success in today's climate (and what new challenges do you think you'd face)?
  • If you weren’t a CEO, what do you think you’d be doing now?
  • Did one specific moment spark your passion for [whatever industry they’re in] - if so, what was it?
  • What’s the hardest business decision you have ever made, how did you make it, and how did it turn out?

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