Questions to Ask CEO during an Interview

CEOs are dangerous people — and that’s appropriate. They’re trying to change the world, heading into battle with small resources and big ambitions.

Therefore spend two-thirds of your interview time gauging whether this CEO has the courage and focus needed to rock the status quo. Give your CEO a chance to show how he/she has built a powerful little fighting machine — and to fill you in on what’s coming next. What’s more, focusing on strategy, vision and culture will be pleasing to the CEO’s ears. He or she will be more likely to decide that you “get it” and belong at the company.

CEOs can be dangerous bosses. They can be moody, impetuous, aloof, contradictory and a whole lot more. In fact, some teeter on the edge of clinical insanity. So you want to slip in a few questions that will help determine whether life in this CEO’s world will be dangerous for you or not. As you do so, step carefully. Ask questions that let you glimpse the CEO’s style without making it seem like you’re disrespectful or hostile. Among the ones that I like:

  1. What’s the most important thing you’re working on right now, and how are you making it happen?
  2. Take me through the skills of your top team members. What is each person best at?
  3. What’s the hardest decision you’ve made so far?

The CEO is the keeper of the vision and of the strategy.  If they are also the founder, they are also the keeper of the culture. So if you have an opportunity to meet with the CEO of a company, use that time to assess if you really want to join the company. 

Dive into the strategy.  Don’t just ask the first-order question (“what is your strategy”), ask the second-order questions.

Ask them how they define their culture.  See how the CEO’s answer compares to the culture answer from others you have asked. Is the company in sync on what the culture is? Or do different departments have a very different view on the culture?  And remember: culture is defined on how a company is different. So if a CEO talks about ping-pong, yoga, food-truck Fridays, and high-end beer bashes … then they haven’t really thought about culture. 

Lastly, don’t waste the CEO’s time with questions you can ask just anyone.  Think about what you want to ask her beforehand (write the questions down). Preparing for the interview will give you the best chance to assess the company … and preparation also makes you look good in the eye of the CEO.

Worst thing you can do is not to ask any questions.  That is a big red flag to most CEOs and you’ll be passing up a huge opportunity to get deep information about a company you might want to join. So come prepared.

3 Comments to Questions to Ask CEO during an Interview

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