Interviewing With A CEO? Ask These 4 Questions

At some point in your career, you may have the opportunity to interview with the CEO of the organization where you are applying for a new job. In most cases, the CEO is interviewing you because you are candidate for a position that is one of their direct reports on the executive team. If the role doesn’t directly report to the CEO, then it has enough strategic value to the organization, such that the CEO is interviewing you to give the hiring manager their stamp of approval (or not).

Don’t focus so much on impressing the CEO as you focus on connecting with them — people hire people they like and want to work with. If you’re interviewing with the CEO, you’ve likely already passed a screening of your professional experience and technical abilities. Be confident, yet humble, and stay curious throughout the conversation.

As with any interview, it’s important to ask questions to not only show your interest, but also demonstrate your curiosity. Recognize that the CEO is quite busy, so you may not have a lot of time with them. It will be important to prioritize your questions and have them ready to go when the tables turn and you have a chance to pose some questions of your own.

Keep in mind that some of the best questions will arise organically from the conversation in being naturally curious. “Say more about that...” or “tell me more about that...” are always good ways to get someone to dive deeper and provide more detail so that you can probe into their responses with more questions.

You want your questions to be intelligent (versus something that can be easily answered online), thought-provoking for the CEO, and elicit enough information for you to assess if it’s a place where you’d want to work — and a team or boss with whom you’d want to work.

Time permitting, ask the following four questions in your interview with a CEO:

Question 1: What culture does the organization need to succeed in the coming years and what are you doing to build that?

Culture is how things get done in the organization, and it comes from the top. The CEO sets the tone for what behaviors are encouraged, rewarded, or tolerated. In fact the “and what are you doing to build that?” part of the question may be a wake-up call for the CEO as it squarely asserts their responsibility for this, which not all CEOs are fully conscious of or attuned to.

It’s also important to assess how the organization’s cultural values are reflected in everyday behaviors — or are they just lip service? How are these values woven into the fabric of organization’s policies, processes, and practices? And how consistent are they with your own personal values?

Question 2: What are the top priorities for the organization in the coming year, and what has the potential to distract the team from these?

This question helps create clarity for you on the CEO’s vision of what’s most important for the business and how realistic they are about what could derail the team and the organization. Are they brutally honest in their assessment of where the team could go off-track or are they overconfident in the team’s abilities or blind to inherent or obvious risks? Moreover, do the priorities that the CEO articulates excite you and motivate you?

Question 3: What does high performance on this team look like over the next few years, and what’s the biggest obstacle the team needs to overcome to achieve this?

Does the CEO see what will most drive a multiplier effect for the team and expand their collective leadership capacity? Likewise, do they see where they are destroying value (or at risk of losing value) through unproductive patterns? Again, the CEO’s ability to honestly assess the team’s shortcomings is a clue to how well vulnerability is modeled in the organization, the extent to which people are open and honest about what needs improvement, and their willingness to take ownership and responsibility for this.

Question 4: What are you most looking for from me in this role and how will you measure my success?

This is particularly important if you will be a direct report to the CEO, and should be asked of any hiring manager, so that you know what’s most important to your boss and how you’ll be evaluated. Not only do you want to know what ‘good’ looks like, but also you want to know what ‘hitting it out of the park’ looks like.

If you’re not reporting directly to the CEO, asking this question is also a good way to know what the CEO cares about with respect to your role or function, and what will catch their attention (both good or bad) and make an impression on them.

If you forget to ask one of these questions — or another question you wanted to ask or perhaps thought of after the fact — do not beat yourself up. There are an infinite number of questions you could possibly ask, and there’s only so much time. The four questions above will not only help you collect valuable information to assess the opportunity, but also will set you apart as a thoughtful, intelligent and curious candidate.