10 Nov Speaker Spotlight: Steve Gilliland – Keynote Speaker on Humor, Heart, and School Culture
Steve Gilliland is a keynote speaker on humor, heart, and school culture, and a member of the Speaker Hall of Fame. He has presented to more than two million people across 51 industries in all 50 states and 15 countries. Collaborative Agency Group books him for district professional development days, opening day events, and education association conferences.
Why Steve Gilliland Works as a Keynote Speaker for Schools
Teacher and staff audiences are a hard room. They have sat through years of mandatory PD, and they can tell within two minutes whether a speaker respects their work. Gilliland solves that problem the way few speakers can: he is genuinely funny first, and the message lands underneath the laughter.
One newspaper described him as what happens when the humor of a stand-up comic collides with the inspiration of a motivational speaker. For a district that needs a morning session to reset the tone of a building after a long stretch, that combination does more than a lecture on engagement ever will.
A Speaker Hall of Fame Headliner With a National Radio Platform
Gilliland holds both the CSP and CPAE designations from the National Speakers Association, the second being induction into the Speaker Hall of Fame. He can be heard daily on SiriusXM Radio’s Laugh USA and Jeff and Larry’s Comedy Roundup, which means many of your staff will already know his voice when he walks on stage.
He is the author of six bestselling books, including Enjoy The Ride, which spent seven consecutive years on bestseller lists, along with Hide Your Goat, Making a Difference, Detour, Turn the Page, and The Cherry on Top. Enjoy The Ride and Making a Difference both work as full keynote programs.
What Education Audiences Take Away
His core message is about the conscious choices people make every day that affect the people around them, which translates directly to a school building. Making a Difference focuses on positive influence regardless of position or title, a message that works for principals and bus drivers in the same room. Hide Your Goat addresses what to do when other people’s attitudes start driving your own.
He also built a multimillion dollar company from the ground up on the philosophy he shares with audiences, and he and his wife Diane launched the Gilliland Foundation in 2017. The credibility is earned, not borrowed.
Best Fit Events
- District opening day and convocation
- Teacher professional development days
- Education association annual conferences
- Principal and administrator leadership retreats
- All-staff gatherings including support and operations teams
Gilliland also serves on the board of directors for a financial institution and has been recognized by Who’s Who for Speakers and Business Professionals. Districts that book him for an opening day frequently bring him back for a mid-year session, because the message holds up when a staff is tired rather than fresh.
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The Bottom Line
Steve Gilliland is the booking for a district or education association that wants a Hall of Fame headliner who will leave a staff laughing and thinking at the same time. Spring and summer 2027 PD dates book early for speakers at his level. Check his availability and current fees on his profile.
Ready to check Steve Gilliland for your 2027 event? Tell us your date, audience, and budget, and we will confirm availability and current fees. No obligation.
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