Booking calls tend to follow a script: are you free, what do you charge, what do you speak about. All three are necessary. None of them predicts whether the session will land.
Here are the ones that do. I have answered all of these many times, and the pattern is consistent: the organisers who ask them end up with better events, including when they book someone else.
Before you talk to anyone
1. What does this session have to achieve?
Ask yourself first. Open the conference and set a frame? Send people home ready to act? Give a difficult message a friendly face? These need different speakers. An undefined slot is the single most common cause of a disappointing keynote, and no speaker can fix it for you.
Questions for the speaker
2. What is the one idea people leave with?
If it takes more than a sentence, the audience will not retain it either. This one question filters more effectively than any other.
3. What would you need to know about our audience to make this work?
Listen for questions coming back. A speaker who responds with reassurance is planning to deliver what they already have. A speaker who asks what decision your people are avoiding is planning to build something.
4. What actually changes for our version of this talk?
Push past "I will use your industry's examples". Ask what structurally differs. It is a fair question, and the honest answer is sometimes "not much", which is fine if the fee reflects it.
5. Can I watch a full session, not a highlights reel?
Reels prove someone films well. A complete talk proves the argument holds for forty-five minutes. Any speaker who cannot produce one full recording is asking you to take a large purchase on trust.
6. What have you got wrong on stage, and what did you change?
The best answers here are specific and slightly uncomfortable. Everyone who has spoken a lot has misjudged a room. Someone who cannot name an instance is either very new or not reflective, and both matter.
7. What do you need from us, and by when?
Good speakers have a preparation process and will tell you its shape: a discovery call at this point, content locked by that point. Vagueness here reliably becomes chaos in your final fortnight.
8. What else will you do while you are here?
Panels, a Q&A, a leadership breakfast, photos, a piece of content for your channels. Much of this is often included if you ask before contracting, and expensive to add afterwards.
9. What are the terms if either of us has to cancel?
Unromantic and essential. Deposit, cancellation windows, force majeure, who pays for changed flights, and whether you may record and reuse the session. Settle recording rights before signing, not in the green room.
"What would you need to know about our audience to make this work?" The shape of the answer, questions back or reassurance, tells you which kind of speaker you are dealing with in about thirty seconds.
Questions to skip
"Have you spoken in our industry?" Weak predictor. Useful for two minutes of credibility, then irrelevant. Outsiders often see what insiders have gone blind to.
"How many people have you spoken to?" Measures career length, not fit.
"Can you do it for less?" Fine to ask, but ask for a trade rather than a discount. Extra sessions or flexible dates give both sides something to work with. There is more on this in what keynote speakers cost in 2026.
Finally
Ask them what they would do if they were you. Any speaker worth booking has watched dozens of programmes from the inside and has opinions about slot placement, session length and what follows a keynote. You are buying that judgement as much as the talk.
If you want to run these past me, the availability form is the fastest way, and you can see how I structure a session on the keynote page first.
Frequently asked questions
Is it rude to ask a speaker what could go wrong?
Not at all, and the answer is revealing. Speakers who have done this a lot have watched sessions fail and can tell you exactly which conditions cause it. Speakers who say nothing could go wrong have either been lucky or are not paying attention.
Should I ask for references from past clients?
Yes, and ask for one whose event was similar in size and format to yours, not just the most impressive name on the list. A great session for 2,000 people says little about a 40-person executive offsite.
What if the speaker will not customise?
That is a legitimate model, especially for speakers whose talk is the product. Just price it accordingly and place them where a fixed talk works, which is usually an opening slot rather than a closing one.
How much should I tell a speaker about internal politics?
More than feels comfortable. If there is a decision your leadership is avoiding, or a restructure nobody is naming, a speaker who knows can work with it. A speaker who does not know will walk into it live.
Sources: Executive Speakers Bureau - questions meeting planners should ask · ProSpeakers - booking timelines and fee ranges