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How to Make a Great Impression When Speaking to Senior Leadership

“What the hell am I looking at here?”

We were only 5 minutes into our meeting with the CEO when things started to go sideways.

I was the newly hired Sales Trainer at a software company, and my boss and I had prepared a comprehensive plan for training an incoming wave of new sales recruits.

Unfortunately, we didn’t get very far in our presentation before the CEO and the Head of Sales started ripping it apart. We left that meeting defeated and went back to the drawing board.

The lessons I took away from that C-level meeting–the first of many in my career–totally changed the way I think about speaking to senior leadership.

Here’s the weird thing: the plan itself wasn’t actually the problem. The real problem was we spent a lot of time making the plan, and zero time thinking about how we would communicate and deliver the plan to our executive audience.

Here I share what I’ve learned about speaking to senior leadership, so hopefully, you can avoid the pain that I felt on that day.

Show up with confidence

If an executive is going to endorse your recommendation, they want to know that you’ve done your homework and that you can defend your ideas. So it’s important you project a confident presence. And confidence is best forged through preparation.

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Know your opening cold

When speaking to senior leadership, make sure you’ve memorized your most important points, data, and stories. End with a stirring call to action. And practice, practice, practice, until you can jump in and out of the presentation without skipping a beat.

If you’re not comfortable with your content or with your own speaking ability, the chances of your presentation being effective go way down.

Don’t bury the lead

If you’re speaking to senior leadership, it’s probably because you want them to take action on something. They understand this dynamic, so don’t beat around the bush.

I think about it in terms of journalism.

When young journalists are learning to write news stories, most of them learn the “inverted pyramid” method, which teaches you to begin your article with the most newsworthy information (i.e. the lead), then prioritize the rest of your material in order of its relative importance.

We should use the same principle when speaking to senior leadership.

Do you need a decision? Are you asking for more budget? Do you have urgent questions that need to be answered?

State those things up front, so everyone is on the same page and can move toward a decision quickly.

Demonstrate your reasoning clearly

One of the tricky things about presenting to executives is knowing how much detail to provide.

Some leaders want A LOT of data before moving forward with a decision. Others might make snap judgments based solely on your agenda slide.

A good rule of thumb is to have two or three solid points for every pillar of your recommendation. But the real key is to know your audience well and construct a presentation that’s empathetic to how they process information.

In the example above, our CEO had low patience for anything he already knew or agreed with, but he would dive deep on a topic if he wasn’t yet convinced about it.

So the second time I presented to him, I gave him an executive summary with four main points, then stored additional data in an appendix that I could easily access if he wanted to drill down.

Be honest about gaps

After years of getting pitched half-baked ideas, most execs have a pretty good B.S. meter.

Acknowledging holes in your data or weaknesses in your argument can be intimidating, but it’s also a great way to show you’ve done your due diligence and it engenders trust with your audience.

In fact, most senior leaders are enthusiastic problem solvers and will gladly volunteer ideas or resources that you haven’t thought of yet.

After we botched that first meeting with the CEO, we were lucky that we got another chance. We made a few adjustments to the plan itself, totally re-worked the strategy for communicating the plan, rehearsed it ahead of time, and then knocked it out of the park in the second meeting.

Of course, you won’t always get a second opportunity when speaking to senior leadership. But if you follow the steps above, one chance should be enough.

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Illustrated by Jonathan Valiente