Five Questions to Ask a Speaker Before You Sign the Contract

By Marques Ogden · Updated September 2026

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The best predictor of whether a keynote lands is not the speaker's highlight reel. It is the conversation you have before you sign. After years on the speaking circuit, here are the five questions I would ask any speaker, including me, before writing the check.

1. "What will you need from us before the event?"

The answer tells you whether you are buying a performance or a partnership. A speaker who asks for a discovery call, your company's current challenges, and the language your people actually use is going to build something for your room. A speaker who only needs your logo and an AV spec sheet is going to deliver the same talk they gave last Tuesday in a different city.

2. "Tell me about a talk that did not go well."

Every working speaker has bombed somewhere. I have. What you are listening for is ownership. A speaker who blames the audience, the venue, or the time slot will do the same to you. A speaker who tells you what they learned and changed is someone who treats the craft seriously. I ask my own clients hard questions about failure because my whole story is about what collapse teaches you. I expect the same honesty from anyone on a stage.

3. "What happens after the keynote?"

A great keynote opens a door, and most organizations let it swing shut by Monday. Ask whether the speaker offers follow-up sessions, workshop add-ons, discussion guides for managers, or a way to keep the message alive in the weeks after. If the answer is nothing, you can still book them, but plan the reinforcement yourself or accept that you are buying a memorable morning rather than a change.

4. "Who is your message NOT for?"

This one filters out the pretenders fast. A speaker who claims their message works for every audience has not thought hard about any audience. My story about losing my NFL money and rebuilding from the bottom hits hardest with teams facing real adversity: layoffs, leadership change, a market turning against them. For a victory-lap celebration event, someone else might serve you better. A speaker who can say that out loud is a speaker you can trust.

5. "Can I talk to two clients from the past year?"

Not testimonials on a website. Phone calls. Recent ones. Five minutes with a past client tells you more than an hour of demo video: did the speaker prepare, was the offstage experience professional, did anything change afterward. Any established speaker can produce two names in a day. Hesitation is your answer.

Ask these five and you will not need luck on event day. If you want to put me through the same questions, book a call here.