How To Interview With A Company’s CEO — And Nail It

When it comes to most professional roles, particularly the openings that you might encounter early in your career, you can expect to conduct your interviews with either a hiring manager (the manager to whom you’d directly report if offered the position) or with an HR representative or, in some cases, with both. 

However, interviewing with very senior members of the staff, up to and including the chief executive officer, is an experience typically reserved for specific individuals applying for specific roles. 

Read on to find out when you may be expected to chat with the CEO during your interview, which questions she may have for you, and which questions you may find especially valuable to ask her during the process.

When can you expect to interview directly with the CEO?

If you’re applying for a job at the entry level or even for a mid-career role, you likely won’t be asked to sit down with the head of the company during the interview phase. However, a few exceptions to this rule certainly exist, and as you rise up on your own career ladder, the likelihood of interviewing with a CEO increases. Below, you’ll find three scenarios in which you can anticipate a conversation with a CEO while being interviewed.

• If you’re applying for a job in senior management, then it’s likely that the CEO will want to weigh in on your candidacy. In very large companies, regional directors and other higher-ups might assume that responsibility in place of the CEO (for instance, Jeff Bezos can’t interview every manager at Amazon, but he offers his hiring managers clear instructions for what to ask and which criteria to evaluate). Massive conglomerates aside, however, most CEOs will take an interest in speaking to prospective directors, high-level managers, and others in roles that will oversee numerous employees and/or an entire department. 

• If you’re applying for an administrative role that necessitates regular contact with the CEO (like an open executive assistant position), then she’ll most likely want to interview you before moving on to the offer stage. Some CEOs do leave this task up to their direct reports (like if the CEO is located overseas but wants a dedicated EA in your location), but it’s safe to assume that a CEO will want the opportunity to speak with and select her own assistant.

• If you’re applying for a position in a very small company, then the CEO may be more hands-on than usual. This is especially common in early-stage start-ups; in a company with only 10-20 employees, staffers of all levels will interact on a more regular basis than they might in a company with thousands of employees and numerous offices. These are the most typical scenarios in which a CEO would involve herself in the interview process for an entry-level employee.

How do you prepare for this type of interview?

Interviewing with a CEO requires a different level of prep work than a conversation with a hiring manager or an HR rep, and these actions will help position you in the best possible light.

Be sure to thoroughly research the company.

Remember that interview scene in “The Devil Wears Prada” when Andy (Anne Hathaway) didn’t know that Miranda (Meryl Streep) was the editor of "Runway Magazine," even though she was specifically there to vie for a role as Miranda’s assistant? That failure to read up on Runway and educate herself on who’s in charge and what the organization represents would never fly in a real-life interview scenario with a CEO. 

No one’s expecting you to be a certified expert on the company, but definitely take some time to look over their website, to familiarize yourself with their mission statement and recent achievements, and to find convincing ways to connect your own past accomplishments and experiences with the company’s goals. 

Arrive on-time and ready to go.

Of course, every interviewee should carefully plan her commute and arrive at the interview location right on time, if not a couple of minutes early. But when you’re meeting with a CEO, who presumably has numerous other meetings and obligations to address on any given day, punctuality becomes especially crucial. Make sure to walk into the building at your scheduled time and ready to immediately sit down for your interview.

Study the job posting carefully.

When very high-ranking executives like CEOs attend hiring interviews, they’re usually most interested in solving their staffing needs as efficiently as possible. They want to know how the prospective candidates will manage to excel in the vacant role, and they want to know what these applicants can bring to the table in terms of experience, hard skills and industry contacts. 

Interviews should always be two-way conversations, in which you’re evaluating the company even as they’re evaluating you. But to help yourself with the second part of that equation, spend some time thinking about the language used in the posting and how you can frame your background and accomplishments to address the needs expressed in the job description.

Which questions can you anticipate from a CEO?

1. What appeals to you most about this company?

More than a mid-level manager or even a senior manager or director, a CEO wants to know why you’re specifically interested in working for their company. So rather than offering up explanations for why you want to build your career in a particular industry, try to hone in farther and prepare talking points for why that company is a great fit for you. What do you like about their policies? What sets them apart from other companies within the same field? The more detail-oriented you can make your responses, the stronger an impression you’ll make. 

2. Tell me about a difficult work situation that you solved and how you solved it.

Because they need to take responsibility for all aspects of their business, CEOs value team members with strong problem-solving skills and the initiative to rectify issues before they become too large to address. The ability to speak clearly and eloquently about your past experiences thinking on-your-feet at work will serve you well in this interview context.

3. What type of work culture do you thrive in?

CEOs often play a major role in defining their company’s “culture” and overall energy. Therefore, they have a vested interest in hiring individuals who seem like good fits for their workplaces and offices. However, because work culture can largely affect an employee’s overall happiness at work, honesty is your best bet when answering this question. You don’t want to be stuck in an office 40 hours a week with vibes that don’t suit your personality or your workflow. Be polite and cheerful, but don’t fall into the trap of just saying what you think the CEO wants to hear. 

Which questions should you ask a CEO?

1. What makes you proudest about this company?

CEOs invest a great deal of time and energy into their companies, and most appreciate the opportunity to talk about what the organization has accomplished and how they and their team members have affected positive change. Also, the CEO’s answer to this question can provide you with useful information about how the company’s leadership arranges their priorities and where you could fit into that dynamic.

2. How is the company working to grow and evolve to keep up with new industry developments?

Understanding how the head of the company views growth and where her aspirations lie will give you a useful view into where the organization could be headed in the future and whether it makes sense for you to join them on that journey. 

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