Retreat hosts aren’t just booking a speaker, they’re inviting you into the most intimate room they’ve built. That changes everything.
In this final episode of our speaker selection series, I’m pulling together my favorite clips from interviews with incredible retreat hosts inside my course, the Sought-After Speaker System. This time, we’re zeroing in on retreats: what makes them different, how selection works, and what hosts truly value in a speaker.
Listen in as Tomasha Suber, Frances Ledgewood, and Heather Leicy & Jamie Fischer join us to share what they’re looking for when they select speakers for their intimate experiences.
These clips are part of a larger speaker interview series inside of Sought-After Speaker System, my course for speakers. Check out the full uncut interviews inside the course.
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Retreats are small by design. They’re built to foster connection, depth, and transformation. That also means that who is invited to speak—and how they show up—has an outsized impact on the entire experience.
Unlike conferences where you may deliver a keynote and disappear backstage, retreats require you to be present, invested, and aligned with the energy of the room.
It’s not just about your ability to teach a great topic. It’s about your ability to lead, mentor, and engage in real-time. It’s about being a contributor to the experience, not just a name on a schedule.
What Real Hosts Are Saying
Inside the Sought After Speaker System, I interviewed three incredible retreat hosts (technically four!)—each with a very different audience and model—but they all said versions of the same thing: they’re not just picking speakers based on resumes.
Tamasha doesn’t take applications. She hand-selects speakers after watching them for a while—online and in community. She’s looking for people who live what they teach, because her attendees don’t just need inspiration—they need real-world alignment and depth.
“I want to watch how you move. I want to see if your content matches your character.” – Tamasha Suber
Frances is hosting her first retreat for wedding stationers, and with only 12 attendees, she’s prioritizing intimacy. Her speakers need to feel like mentors in the room, not just presenters.
She wants women who get the industry-specific challenges and can connect both in front of the group and in quiet conversations over coffee.
“It’s not about who’s the most polished. It’s about who can hold space and be real.” – Frances Ledgewood
While Conquer Live is technically a conference, Heather & Jamie intentionally build it with a retreat feel—high trust, small group energy, and deep interaction.
They invite people who are already present in their community: active in the Facebook group, showing up to conversations, already aligned with the values of the space.
“If you already feel like part of the room, we’re more likely to ask you to speak in it.” – Jamie & Heather
What This Means for You
So how do you actually get selected to speak at a retreat?
Show Up Before You Pitch
Engage where the host is already building community. Comment on their posts. Share their content. Show up in their DMs with genuine encouragement—not an ask.
Be Consistent with Your Message and Your Presence
Retreat hosts aren’t just looking at what you say in your speaker one-sheet. They’re watching what you say everywhere else—your stories, your posts, your responses.
Be the Kind of Speaker Who Can Mentor in the Moment
This isn’t about charisma—it’s about character. Are you approachable? Relational? Comfortable with depth? That matters more than your credentials in these spaces.
Why Retreats Are Worth Pursuing
Retreats can change your business—and your life.
They’re where real relationships are built. Where you’re not just remembered as a speaker, but as someone who helped shift someone’s trajectory in a hallway moment or quiet conversation.
They’re also a unique form of visibility. You walk away with depth of connection that no large event can match. And in a noisy digital world, depth wins.
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