I have been on both sides of the keynote booking conversation — as the speaker being evaluated and, in my corporate life, as the executive helping select speakers for our annual leadership conference. The difference between a keynote that changes how people think and one that fills a time slot is significant, and it is usually apparent before the speaker ever takes the stage.
First: will you customize this talk for our audience? A speaker who delivers the same talk to a room of healthcare executives and a room of technology startup founders is not serving either audience well. The best speakers do pre-event research — a call with your team, a review of your industry challenges, an understanding of what your audience already knows. If a speaker cannot articulate how their talk will be different for your event, they are selling a performance, not a partnership.
Second: what will my audience be able to do differently on Monday morning? Entertainment has its place, but if you are investing in a keynote for a professional audience, there should be practical takeaways. Ask the speaker to describe the specific frameworks, tools, or perspectives your attendees will leave with. If the answer is vague, keep looking.
Third: can you share references from similar events? Not testimonials on a website — actual references you can call. Ask those references specific questions: did the speaker customize? Did they engage with attendees before and after? Did people reference the talk weeks later, or had they forgotten it by lunch? Fourth: what does your fee include beyond the stage time? The best speakers invest significant time before and after the event. Fifth: what is a topic you have changed your mind about? This reveals intellectual honesty and the kind of rigorous, evidence-based approach that produces talks worth listening to.