How to Choose a Keynote Speaker for a Leadership Event

It's tempting to choose a keynote speaker the easy way. You watch a showreel, read a few testimonials, check the fee against the budget, and pick whoever looked best on a big stage.

I understand why. But a showreel only shows you how someone performs. It doesn't show you where their message comes from.

And for a leadership event, that's the part that decides whether your managers walk out with something they'll use, or with a nice memory of an hour that had nothing to do with their Tuesday.

So here's the test I'd use first, whoever you end up booking: is this speaker's message still being tested against real people, one at a time?

The question a showreel can't answer

When you stand on a stage and the lights aren't blinding you, you can see faces. That's one of the reasons speakers love the job. The feedback is instant.

When a talk really lands, you can watch it happen. Different parts of the audience nod at different descriptions, because each group recognizes itself in a different moment. You can't fake that.

But I'll be honest about something. I couldn't make that happen if all I did was speak. What makes it possible is the coaching work I keep doing, one person at a time, in my practice.

Knowing what's really going on in people's lives, what they connect to, what leaves them cold and what actually moves them, is not something you learn from big stages. You definitely don't learn it from videos or social posts. You learn it from direct contact with people. No barrier between you.

I tell people who want to teach the same thing. If you want to speak to parents about parenting, spending the next few years at an unrelated desk job while you read about it won't help you much. Spend a couple of months volunteering with kids and suddenly you have real experiences tied to what you teach. You have to live your field, not only study it.

The same applies to leadership speakers. Ask yourself: when did this person last sit across from a manager who was stuck?

What small rooms teach that big stages hide

Teaching someone one-on-one isn't glamorous. You repeat yourself. You check that they understood. Then they come back and tell you it didn't work.

Here's a typical example. Someone learns how to have a difficult conversation. A month later they say it failed. The other person got annoyed and ignored them. So you ask what exactly they did, and it turns out they never had the conversation face to face. They sent a text message.

You only discover that kind of thing up close. And once you've seen it enough times, you stop teaching the clean version of the idea. You start teaching where people will cut corners, and where it gets emotionally hard for them, because that's where the idea usually dies.

That's the difference you feel in the audience. A speaker who has only rehearsed the message describes how things should work. A speaker who has watched people try it describes the moment you're already stuck in.

When I train group facilitators, there's one tip I repeat more than almost any other: talk with your participants one by one. Grab personal time with the people who show up to your workshops and lectures. As many as you can at the beginning. Later you can do it less often, but you have to keep doing it. The risk of losing touch with the field is real.

What "spoken to personally" looks like in a big room

One of my NLP teachers taught a group of several dozen people. Some of us were already teaching our own courses. Others were complete beginners. And week after week, almost everyone looked happy to be in the room. Even when someone asked the most basic question and he answered slowly and patiently, the people who already knew the answer enjoyed listening.

I wanted to understand how he did it, so I watched him closely, including in his private conversations with students. The secret wasn't in his words. He genuinely saw each person as the best version of themselves, already there. It came through in how he looked at them. And because it was real, people felt it as real.

That's what you want from a keynote speaker. Not a performance aimed at "the audience", but a person who can make each individual feel seen, even in a large hall.

Part of that is a skill you can check for. I don't speak to a room of NLP students the way I'd speak to kindergarten staff or to an open audience. Just knowing who chose to be in that room already tells me where to start the conversation.

It goes down to the words. I wouldn't speak Hebrew to someone from France. Same logic applies when I step into a group or industry that isn't mine yet: I make it a priority to pick up the language first, because so much power sits in the small details.

It even goes down to pace. One-on-one, I slow down for people who need it. In front of a group I can't do that for each person, so I need a different solution. Many people who prefer a slower pace don't really need me to talk slowly. They need pauses. A good speaker has thought about these things for your people, not just for audiences in general.

Five questions to ask before you book

You don't need to be an expert to spot this. Ask a few simple questions and listen to how the speaker answers.

1. Who have you worked with up close lately?

Before my very first lecture, I had already coached people through a demanding program, one-on-one, week after week. I walked on stage knowing I had proof of what I could do, even if I didn't have proof yet as a speaker. A simple, honest answer like "over the past year I've worked with this many people, on this kind of problem" tells you more than any stage photo.

2. What are your credentials?

Watch how they answer. Confident professionals name their two or three strongest and move on. For years, when someone asked me, I just said I'm an NLP master, even though I'd studied plenty of other things. When someone lists everything they've ever studied, it often comes from insecurity, and the list of unrelated trainings confuses more than it convinces.

3. How will you adapt this to our room?

Fifty people isn't an intimate session. It's already a big talk. And frankly, no single format holds up cleanly from fifty people to a hundred. What matters is creativity and fit. A good speaker will tell you exactly how they'd adjust to your size and your format.

4. Which words won't land here?

Some words close doors in organizations, even when the idea behind them is sound. A speaker who knows your world will talk about the outcome your people care about, like how decisions get made or how change actually happens, without hiding anything, and with real examples behind it.

5. What are you promising, and what comes after?

Be careful with a speaker who promises the keynote will transform your organization. I tell the speakers I coach that the biggest fear of the person booking them is a promise that doesn't come true in front of a skeptical room. A great keynote is a strong, useful opening. Deeper change usually comes from what follows it, such as manager or leadership development inside the company. Ask the speaker what they think that next step looks like.

Where my keynote comes from

Everything I bring to a stage comes from the same place as this article. I still work with people one-on-one and in small groups, and that work keeps shaping what I say to a room of hundreds.

My keynote, No Suit Required, is built on the TRUE model of authentic leadership from my book. It's about turning leadership from something people put up with into something people go all-in for.

But even if you book someone else, use the test. Find the speaker whose message is still being checked against real people, one conversation at a time. That's the one your managers will feel is talking to them.