I have been on both sides of this conversation. As a keynote speaker who has worked with associations, insurance companies, colleges, government agencies, sports tourism organizations, and food and beverage companies, I have heard almost every version of the vetting process. Meeting planners who ask sharp, direct questions before booking almost always end up happier with the result. So I want to walk through the questions I get asked most often, and give you an honest look at how I answer them.
Why the Right Questions Matter Before You Book
A keynote is not just entertainment. It is an investment in how your people think, lead, and perform after they leave the room. Before you sign a contract, you want clarity on the speaker’s message, their story, and how well they can adapt both to your specific audience. Here are the questions that get you there.
“What Is Your Core Message, and How Does It Apply to Our Audience?”
This is the first question every serious planner should ask, and it is one I welcome. My keynote, Now What?, is built around two ideas: performing under pressure when the stakes are irreversible, and leading through sudden, forced change. When a group asks me this question, my answer is simple. I do not deliver a generic motivational talk. I built this message around real moments where the plan disappeared, and the only path forward was to decide, right then, what came next. That framework applies directly to leadership teams navigating restructuring, safety professionals managing high-stakes environments, or sales teams adjusting to a shifting market.
“What Is Your Story, and Why Should We Trust It?”
Credibility matters, especially for a speaker asking an audience to rethink how they handle pressure. When I get this question, I point to specifics rather than vague claims. I am the only American to win Olympic gold in BMX Racing, a sport I competed in at the top five in the world for over ten years. I represented the United States more than fifty times across more than twenty-five countries. Those numbers are not there to impress anyone. They are there to show that the pressure I talk about on stage is pressure I have actually lived inside, over and over, on the biggest stages there are.
“How Do You Customize Your Talk for Our Industry or Event?”
No two audiences are the same, and a good speaker should never treat them that way. When an insurance company asks me this, I talk about risk and irreversible decisions. When a college asks me, I talk about identity and direction after a plan falls apart. When a government agency or sports tourism organization asks me, I shift the examples toward operational pressure and public accountability. The core framework stays the same, but the language, the examples, and the takeaways get built around the room I am walking into. I always ask planners about their industry, their current challenges, and what they want the audience to feel walking out, before I ever write a word of the talk.
“What Happened in Tokyo, and How Do You Talk About It?”
This question comes up more than any other, and I always answer it directly. In 2021, I crashed at forty miles an hour during the Tokyo Olympics, suffered a traumatic brain injury, and was unconscious for five days. That crash ended my BMX racing career permanently. I do not frame it as a setback I pushed through or a comeback story with a tidy ending, because that is not what happened. What I share on stage are the three things that experience actually taught me: gratitude, resilience, and perspective. Audiences respond to that honesty because it is real. Nobody wants a manufactured triumph. They want to know how someone rebuilds direction when the plan is truly gone, and that is the heart of Now What?.
“Can You Provide References or Video Footage?”
Always ask this, and always ask a speaker who hesitates to answer it clearly. I provide event footage, references from past clients across multiple industries, and a direct look at how I have adapted the same core message for different audiences. A speaker who cannot show you real footage or real references is asking you to book on faith alone, and that is not a fair ask for the size of this decision.
“What Is Included in Your Fee?”
This question protects both sides. I am upfront about what is included in my fee, what counts as an add-on, and what my availability looks like for pre-event calls, custom content, and post-event follow-up. Clear expectations here prevent surprises later and let you budget with confidence.
A Simple Way to Start the Conversation
If you are vetting speakers for an upcoming event, ask these questions of every person on your shortlist. The answers will tell you almost everything you need to know about whether they are the right fit for your room.
If you are looking to hire a motivational speaker, I would be glad to answer these questions directly for your event. Visit connorfields.com to learn more about Now What? and to start the conversation about your next keynote.
– Connor Fields
