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How do You Start a Conversation with a CEO

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start a conversation with a CEO

Conversation with a CEO

CEOs are just common people. But Common people who run billion-dollar companies and accomplish amazing things. While having a conversation with a CEO few things have to be known.

Considering the elegant and professional nature of your average CEO, when we find ourselves in a position to interact with someone at this level, we think it is very natural for most of us to feel a faint sense of anxiety or fear. For the first time, passing the elevator or giving a presentation.

When you think about contacting your CEO, do you find a mild case of anxiety? To pay homage to our Best CEO Award, read the tips for keeping your own in a few common office situations.

Interviewing with a CEO

You don’t want to read through the Glassdoor Interview Questions & Answers to know that a standard interview with a hiring manager can be intense. But interviewing with the CEO adds a whole other level of coercion: You are speaking with the most experienced, invested, and authentic person in the company, and his opinion of you will have a strong impact on whether or not you get the job.

Presenting to a CEO

One of the biggest stereotypes associated with CEOs and top executives is that they are busy – they often show up late for your meeting or look at their phone while talking about an important topic. This takes us to your first task of keeping your own when presenting to a CEO during a meeting: not taking his behavior personally.

Having a casual conversation with a CEO

You have heard consistent advice about talking to important people: Be yourself. Do not talk politics. Learn when to leave the conversation.

But if you really want to impress a CEO – or walk away from the conversation without feeling like your foot is in your mouth the following, we suggest going to work with some conversation starters in your pocket, like the following:

  • Ask about a recent business trip

  • Appreciate the latest attempt, keynote, or product release

  • Ask for suggestions on job-appropriate things such as where to take a customer for lunch or what local locations you should recommend to a prospective employee visiting the city on the weekend.

  • Compliment a way of clothing or accessory he is wearing and explain why you like it (but only if you can be genuine!)
  • Inquire about his past or future weekend plans (depending on which end of the week is approaching)

As with most relationships, how you say something is just as important as what you say. With a little preparation, you can be ready for a warm, casual conversation with your CEO.

Every person has their own personality and style. The following information should be digested as mere practical recommendations that have consistently worked for accounting agents when contacting more than 500 companies over the past 30 months. If the information is given a useful, take it.


Realizing our call anxiety is a positive factor. 84% of all marketers and sellers are reluctant to call.

Progress is the first sign that a problem is developing. As soon as you get in touch with a prospective CEO or his/her executive assistant you will return to calling only at the I/S level.

Tailor the call for the good of the future. Show value for their personal profit.

One of the primary causes of telephone fear is the failure to set a goal for the call. Keep a clear picture in your mind of why you are calling and where you can call.

Provide a benefits report to the executive assistant after the introductions. “EA, [My Company] needs to give XYZ Corporation more access to some resources.”

Consider being rejected by the CEO’s EA and embarrassing. It is part of this process. Our job is to cultivate good relations with the EA and show significant value in overcoming their rejection.

Acting as a gatekeeper is EA’s side job, and they work hard at it. There are a lot of gate keys in your experience, use your experience to find out which key the gate opens.

Schedule time on your calendars to invite your CEO to nominated opportunities just as you would a meeting or conference invitation. If it is not on your calendar, it is usually slipping through the cracks.

To build rapport with a CEO remember:

 1. Thank them for taking the time to talk!

 2. Speak with respectful intonations and tones, favor yourself to a CEO. The CEO is the “gatekeeper” and can be your address to success or your instrument of destruction.

 3. Use open-ended questions that may ask which, what, when, where, and how. Purposively worded questions can open the door to huge amounts of useful information.

4. Key on his responses. Insert their thoughts in your questions and responses. They will spend more time with you.

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