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Sitting through multiple interviews for one job is the norm today, as roles are now frequently cross-functional, serving more stakeholders throughout the organization. Consequently, more people need to approve of a new hire. In a lot of smaller and even mid-sized organizations, even the CEO might sit for an interview or two.

While it may seem daunting, interviewing with the CEO is a good thing, not a reason to get rattled. Rest assured, the CEO doesn’t intend to intimidate or heckle you. Many are down-to-earth, approachable people who have achieved their success by genuinely connecting with other people and listening to their perspectives.

At the same time, don’t assume a small-company CEO is small potatoes. Many are serial entrepreneurs or seasoned investors with the same education and skill set as their counterparts in larger companies. They are sophisticated, well-connected, extraordinarily accomplished professionals.

A CEO can come from any background, but what they all generally have in common is that they prefer smart action to smart talk. They like people who understand things quickly, lay out clear options, figure out what to do next, and take action without a lot of prompting. The CEO’s day-to-day job involves monitoring a dizzying number of dials, so their attention span is usually short. Go into your interview with the CEO respecting that fact, and your time together will be more valuable for both of you.

Want to knock your next interview with a CEO out of the park? Here’s some advice:

If the Position Does Not Report to the CEO

In many small organizations, the CEO needs to approve all new hires. They are usually the last person to interview the candidate. If you are interviewing with the CEO but your role does not report to them, you are close to being hired. The rest of the hiring team is confident the CEO will sign off — they aren’t setting you up for failure.

Here are a few tips to make sure the interview goes well:

1. Show that you are the sort of employee who “watches what the boss watches.” Demonstrate that you understand the company’s basic revenue model, competitive position, overall strategy, and your role in it all.

2. Have your elevator speech down pat. First impressions mean a lot to CEOs, and they are almost guaranteed to ask you to “tell me about yourself.”

3. CEOs frame things in terms of business cases, so practice the CAR method for answering questions like, “Tell me about a project you worked on where you had to be especially innovative and creative.”

4. CEOs really like to know what makes people tick. Be prepared for questions such as:

- What about our company appeals to you the most?
- What do you hope to accomplish in your role during the next year?
- Why do you want to work here?

5. Prepare a good softball question, one that encourages the CEO to talk about the company strategy more casually, in their own words. For example:

- What’s your read on a recent major industry event, and how does it affect the company’s position?
- What trends do you see affecting the company the most?
- What is currently happening in the business space that keeps you up at night?

If the Position Reports to the CEO

Successful CEOs, especially entrepreneurial ones, tend to be extremely smart, boundlessly energetic, and former (borderline) criminals. That does not mean they are doing anything illegal today, but it does mean they’re exceptionally street smart. They look for where the rules break down, because that’s where the white space, arbitrage, and innovation opportunities are. They seek out ways to gain an unfair advantage in the market, and they tend to ask forgiveness rather than permission. They didn’t invent the game, but they know what it takes to win.

Successful CEOs want to be surrounded by trusted partners who will complement the organization’s executive talent. They are looking for force multipliers with refined executive presences, people who get to the point quickly, communicate clearly, move things to the next step, and bring energy to the situation.

If you are interviewing with the CEO for a role that reports to them, you need to demonstrate that you are socialized to the executive ranks. Here are a few tips:

1. Make a personal connection early on, demonstrating both likability and, more importantly, similarity. When the CEO asks you to “tell me about yourself,” what they really mean is “tell me something about yourself that reminds me of myself.”

2. Be very careful not to go off on tangents, engage in conversation just to show how smart you are, or offer unsolicited criticism. CEOs know the difference between important details and trivia, and they want to be absolutely sure you do as well.

4. Be sensitive to when it’s time to stop talking. CEOs are surrounded by constant chatter, and they have highly developed listening skills that help them discern when to chime in. Let the CEO have as much airtime as they wish, and show that you are a tactful person who knows when to add value to the conversation.

5. Try to leave a hook when you finish speaking. The CEO should have the last word, not you.

6. Show an appreciation for both the organization’s and the CEO’s business vocabulary. More importantly, show that their vocabulary resonates with you. Be ready to discuss hypothetical business cases using their preferred vocabulary.

Whatever your situation, interviewing with the CEO is something to look forward to. They are eager to meet you. Show that you’re tuned into many of the same things they are and that your previous interviewers made the right choice by recommending you for hire.

LiveCareer develops tools to help job seekers draft cover letters, prepare for interviews, and build targeted resumes via its resume builder and an extensive collection of resume templates.



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