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My first meeting with the CEO of a Fortune 1000 firm was a complete disaster.

How to talk to a CEO:

My first meeting with the CEO of a Fortune 1000 firm was a complete disaster. It was fifteen years ago and despite the cool breeze that was blowing outside, I was sweating bullets. This guy was a titan of industry so my mind jumped frantically between the thrill of the opportunity and the terror of screwing it up.

Entering his office with a huge smile, I instantly vomited verbal nonsense with, “It must be a great honor for you to meet me sir! I can only imagine how excited you are!” Ugh.. I couldn’t believe what I had said and my smile grew increasingly awkward. Excited to meet me?? It sounded like I was being a sarcastic a-hole. With a furrowed brow, he peeled his fingers away from my death grip, sighed heavily and looked at his watch.

The meeting lasted seven minutes.

mr burns homer

Suffice it to say that I’ve learned a thing or two in the decade and a half since that uncomfortable first encounter. And although there are others, the following six items are critically important to successfully maximizing your time on mahogany row:

1. Do Your Homework – When you’re a CEO you tend to be pretty damn visible. Whether it’s a board seat for a non-profit, the latest earnings call, keynote presentations, alumni groups or press releases, you should have no problem tracking down helpful personal and professional information prior to your session. And please, please, please don’t fancy yourself such a master of disguise that you’re going to casually drop some association with their world without looking like a stalker. Instead, simply be aware and prepare for the conversation to naturally flow toward your researched materials.

2. Be Specific - Nothing is more valuable to a CEO than their time. If you are granted an audience ensure that you have a very detailed plan and purpose. Need a decision to be made? Perfect. Have all the relevant pros and cons at your fingertips and the high level numbers and impact in tow. Keep handouts to a minimum. And finally, think through the questions you’re likely to be asked and all possible courses of action so you don’t have to reschedule after you’ve “looked into that“.

3. Ask Questions – Although at times it seems like you should be doing most of the talking, be certain to come prepared with very specific questions. One of the best methods I’ve seen is to literally ask for help. I know, I know… you’re worried that you’ll look weak and that they hired you to have all of the answers. But face facts – the person in front of you ascended for a reason, so take a moment to benefit from their wisdom, guidance and experience.

4. Feed Their Ego – When someone decides that their purpose in life is to lead a multi-billion dollar firm, they just might think a little bit highly of themselves and their abilities. But let me caution you – no one likes a sycophant and CEOs can see suck ups coming from a mile away. Instead of directly complimenting her, find an indirect means to achieve the same end. For example, if the organization recently expanded into Asia you might mention, “… how well the APAC growth strategy has been perceived by the market“. You don’t just enter a new geography without the CEO leading the charge so the message, and compliment, will land.

5. Plan For Redirection – As your session comes to a close you will most certainly be directed to one of the CEO’s lieutenants for follow up and ongoing discussion. As part of your preparatory work you should think through the organizational structure and attempt to shape this outcome to your benefit. In fact, it’s perfectly appropriate to have a name or two in mind and to proactively ask, “Should I plan to run this through [name] as a next step?” They will appreciate the thoughtfulness and recognition that their participation is no longer appropriate or needed. But before you leave, be sure to ask the CEO (or the CEO’s assistant) to notify the subordinate that you’re following up on their suggestion and authority.

6. Say Thanks – This may seem painfully obvious but do take a moment to thank them for their time. I once worked with a colleague who would send hand written thank you notes after all of his C-suite meetings. Whether via the postal system or email, be certain to let the CEO know that you are grateful. One final thought (and this is absolutely critical!!) – be sure to thank the CEO’s executive assistant as well. Be effusive because assistants are both gatekeepers and trusted advisors and you will not get anywhere with the CEO without their help.

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"Do your homework" is so important!

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