The agenda is set, the budget is approved, and the general session slot still needs a name in it. Here is what to ask before you put one there.
Every education director, convention committee, and brokerage event team eventually faces the same decision: a general session slot needs a speaker, the demo reel looks great, the references say the right things, and the clock is running out before the program has to go to print. Under that pressure, most committees end up booking on charisma and availability, because those are the two things a demo reel actually shows you.
Charisma and availability are real qualifications. They are also the two easiest things to fake for forty-five minutes on a stage. What they do not tell you is whether the room will do anything differently on Monday, and for a conference education budget, that is the only question that was ever supposed to matter. I have been the speaker being vetted for this kind of slot, I have sat on the other side of the table deciding who gets it as the former EVP of Learning and Development at Douglas Elliman, and I am REEA's Educator of the Year, which means I have also had to defend my own answers to every one of these twelve.
These twelve questions are the ones that separate a speaker who will fill the room from a speaker who will change what the room does after it empties, and they are the ones I would use on anyone, including myself, before signing a contract.
Prefer to read this as a full story? The Speaker Who Got the Standing Ovation and Changed Nothing →
Ask the speaker this before you ask them anything about themselves. A speaker who answers with an energy level, an engagement score, or a standing ovation is describing the room on the day of the event. A speaker who answers with a sentence like "fewer agents avoiding the follow-up call after a soft no" is describing the room six weeks later, which is the only room your budget was ever actually trying to change.
A new-agent track, a luxury-team retreat, and a brokerage-wide kickoff are three different rooms with three different sets of avoidance patterns, even when the topic on the program looks the same. A speaker who does not ask about production mix, experience level, market conditions, and what the brokerage has already tried is planning to deliver the same session regardless of who shows up. That is a tell, and it is worth asking the question directly rather than assuming the intake call will happen on its own.
A real diagnostic involves a call with the planner, ideally a short conversation with two or three attendees, and specific questions about what the room has already heard and not acted on. A speaker who skips straight from signed contract to finished slide deck is writing from a template, and a template cannot know that this particular convention's agents are avoiding referral conversations more than prospecting calls this year. Ask to see the diagnostic questions before you approve the outline.
Most conference agendas need more than one format from the same speaker across the event: a 45-minute general session kickoff, a 75-minute breakout the next afternoon, maybe a half-day workshop for the managers' track. A speaker who has one 60-minute keynote and stretches or shrinks it to fit whatever slot you offer is not actually flexing the content, they are padding or cutting the same deck. Ask what changes structurally between formats, not just how long the same slides run.
A behavioral session and a CE-approved session are not automatically the same thing. Credit requires learning objectives, a defensible outline, and timing that matches your state or association's standard, submitted on the schedule your approval body requires, not whenever the speaker gets around to it. Ask for the CE paperwork early, not the week before the program goes to print, and ask whether the speaker has actually carried a session through this process before or is proposing to for the first time with your event.
Every speaker has a strong opening story. Ask what they do in the room when an attendee pushes back with something true and specific to that market: inventory conditions, commission pressure, a local brokerage dynamic the speaker could not have anticipated. A speaker who can only deliver the rehearsed version will visibly stall. A speaker who has genuinely diagnosed sales behavior for a living will fold the pushback into the session, because the pushback usually is the pattern they came to talk about.
A good session has a name for the pattern it describes, something an agent can say out loud to a manager or to themselves: a phrase, a model, a diagnostic question. If a speaker cannot tell you, in one sentence, the single idea the room is supposed to walk out holding, the session is a collection of good stories without a handle on any of them, and nothing a room cannot name is a room that can act on it later.
Most conference circuits recycle a small number of topics: mindset, prospecting, time management, AI. Ask directly whether the speaker knows what this audience heard at last year's convention, and what they are doing differently this time rather than relying on energy to disguise a repeat. A speaker who has not thought about this will find out live, in front of your membership, when half the room mouths along with a line they heard from someone else two conferences ago.
Ask for references from other education directors and convention chairs specifically, not just testimonials pulled off a website. Then ask those references a different question than "how was the energy": ask what they noticed change in the thirty to sixty days afterward. A speaker with real behavioral results will have planners who can answer that question specifically. A speaker with only applause will have planners who can only describe the room on the night.
AV requirements, travel, customization calls, handout materials, and recording rights all vary by speaker and are easy to assume rather than confirm. Get the fee itemized in writing before the budget is locked: what is included, what is billed separately, and how many planning calls are part of the engagement versus an add-on. A clean answer here is also a small proxy for how the speaker will handle the rest of the relationship.
A standalone keynote and a keynote with a follow-up mechanism, a workbook, a coaching referral, a half-day workshop for the managers who have to reinforce it, are different investments even at the same fee. Ask what, if anything, is designed to carry the session's idea past the closing applause and into the Tuesday sales meeting back at the brokerage, where the actual behavior change either happens or does not.
This is the question underneath all the others, and it is worth asking yourself, not the speaker. Strip out how good the room felt that night, and ask whether the content, the diagnostic process, and the follow-through would still justify the fee. A real estate conference speaker worth rebooking is the one whose answer to that question does not depend on the ovation at all.
For the broader case on why that distinction matters, see 10 Differences Between a Motivational Speaker and a Behavioral Strategist, the companion reference to this list.
Dr. Jeffrey Scott Stanton, DCH is the former EVP of Learning & Development at Douglas Elliman Real Estate and the founder and Chief Learning Officer of R2R Diagnostic Group, where he helps real estate organizations and agents diagnose and fix the behavioral patterns behind inconsistent performance.
Dr. Jeffrey Scott Stanton, DCH is the REEA Educator of the Year and a real estate conference speaker and instructor for state and local Realtor associations, franchise conventions, brokerage annual meetings, and leadership summits. Every session is diagnosed to the room before it is written.
Every page on this site for the people who book speakers and instructors for real estate conferences, conventions, and brokerage events, written by Dr. Jeffrey Scott Stanton, DCH, REEA Educator of the Year.