17 Questions to ask a Startup CEO in your Interview

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Today, I pulled up a popular question from Quora that thousands of individuals are interested in learning about…”What do I ask the CEO of the startup that I am interviewing with?” From my experience as the CEO of Portlight, I’ve compiled a list of four main topics and 17 questions that will guide you in your next interview with a startup CEO and give you a better chance to knock their socks off.

Understand who the CEO is

The first thing to reflect on while you are preparing your questions to ask a startup CEO is why the CEO exists within  a company. Answer the question:

“What is their role and what do they influence most within the company?

Having a clear and accurate answer to this question will make creating your questions to ask him or her much simpler. For a start, the CEO is the visionary and strategic leader of the company that they reside over. They spend their time imagining the future of the company, strategizing the action steps necessary to achieve that vision, and influencing the team through their leadership style.

Here are the top 4 topics that I encourage you to focus on:

Topic 1: The mission of the company

  1. Why does the company exist? What is its main value proposition?
  2. Who is the company’s ideal customer and how does the company currently approach them?
  3. How did the company get to where it is today?
  4. Can you tell me more about the founding of the company and what the problem is that you were addressing?

Topic 2: The company culture

  1. What are the company’s core values? why?
  2. How do you describe your culture?
    • Is it a culture where ideas and criticisms are welcomed?
  3. What is not allowed within the culture?
  4. Who is the ideal candidate for this company?
  5. Why did you create the culture to be this way? What ideals does it stem from?

Topic 3: The vision of the company

  1. Where do you want to company to be in 3 years?
    • Pay attention to see if they have thought about this before. It may be a bad sign if they appear very unsure of where the company is headed.
  2. What drives you to have this vision? Why are you passionate about this?
  3. How did you create the vision?
  4. Do you think that the company will ever need outside investors?

Topic 4: Strategic Planning and Action

  1. What are the company’s main objectives in the next year?
  2. What are the greatest obstacles for the company this year?
    • How are you planning to overcome them?
  3. How many people are you looking to hire this year?
  4. How do you communicate the strategy to the team?

What to expect from the CEO

The CEO should be able to answer all of these questions at a high level and will be impressed that you are interested in these aspects of the business. Keeping your questions focused on these four areas will lead to a strong and informative conversation with the CEO of a startup company.

How to further impress the CEO

To further impress the CEO, come to the interview with your own ideas and share them if you have the opportunity. The CEO wants people on their team that have the ability to critically think for themselves and can challenge the norms in positive ways. A strong interest and opinion in the matters mentioned above will also indicate that you have potential to grow within the company and become a leader for the team.

To better prepare for your interview with a startup CEO, you can also read my column, The CEO Role: Ins and Outs of a CEO’s Daily LifeIt will give you a more comprehensive understanding of the CEO’s main roles so that you can create even more intelligent questions for discussion at your interview.

Share your Experiences!

If you’re interested in feedback on the questions that you have prepared, email me at Connor@ConnorGillivan.com. For those of you have who have been on either side of the table of the interview, please share other questions that you recommend to readers.

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About Connor Gillivan

He is the co-founder and CMO of EcomBalance , AccountsBalance, and Outsource School. His writing has appeared in Forbes, Inc, Entrepreneur, and other leading publications online. He has scaled multiple companies to 7 and 8 figures per year. He was the co-founder of FreeUp, which was acquired in 2019 by The HOTH. He lives in Denver, Colorado.

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Article Comments

  1. Royce Koenigsman

    March 1, 2016 5:22 am Reply

    I was curious if you ever considered changing the structure of your website? Its very well written; I love what youve got to say. But maybe you could a little more in the way of content so people could connect with it better. Youve got an awful lot of text for only having 1 or two images. Maybe you could space it out better?

    • Connor Gillivan

      March 13, 2016 10:58 pm Reply

      Hey Royce! Thanks for the suggestion. Definitely something that I am considering. Would love to hear other feedback that you have for the site.

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