I’ve spent years in rooms built for learning—rooms with whiteboards, Zoom links, breakout groups, and coffee breaks. So far in 2025, I’ve presented more than 20 workshops and keynote speeches for nearly 3,000 people. My work these days? It’s different.
I’ve been speaking professionally since 1996. Some of those sessions sparked a lasting impact. Others? They filled the time. Reflecting, I think I may have been asking the wrong question. I was asking, “What do I need to say?” when I should have been asking, “What could happen here that couldn’t happen anywhere else?”
That’s the question I ask now…as I walk on stage or log into the next Microsoft Teams meeting. That shift in mindset has changed everything. It reshapes how I show up—not as the presenter or the trainer but as a facilitator of possibility.
Creating Conditions for Connection
My job, I’ve come to understand, is to create conditions for connection, not just the content for instruction. That means releasing control, listening more than I speak, and making space for something unexpected to take root. The emergent. Insight.
I do not come before you to “teach” in the traditional sense; no, not anymore. With an abundance of information a click away, the real value of a live session isn’t in delivering knowledge; it’s in co-creating meaning. That distinction matters.
Because when the person in front of the room stops viewing themself as the expert in the room and starts acting as the convener of something bigger, something more communal, the session transforms. Each experience becomes about connection, not performance.
The most meaningful sessions I facilitate do not depend on how polished my slides are or how many insights I pack into my talk. Instead, sessions are memorable because people connect, genuinely and without pretense. They connect not only with each other, but with the experience, the content, and possibilities. The power wasn’t in what I deliver, but in what they discover—together—when the room became theirs.
I remember one workshop where I ditched the opener entirely. Instead of jumping into a model or concept, I asked each person to write on a 3×5 notecard the answers to these questions:
- As a leader, what are you good at?
- As a leader, what do you want to be better at?
No slides. No long introduction. That was the warm-up activity. A prompt. Then I set a nine-minute timer and asked them to share what they wrote in groups of three (there were 150-plus people in the room). What followed was electric. People turned to one another and started sharing; and they did so honestly, not performatively. By the time we reconvened, we weren’t a room full of strangers anymore. We were teammates. That session wasn’t about my brilliance but the trust I allowed to emerge.
Space, Permission, and Trust
I’ve noticed three things are almost always present: space, permission, and trust. The room needs space to breathe, not just space on the agenda. People need permission to show up as themselves, not just as roles or titles. And trust? It isn’t built through icebreakers or bios; it comes from curiosity, listening, and creating a sense that everyone belongs. As Chip and Dan Heath wrote, moments matter. But not just celebratory moments. Insightful ones.
To consistently create those moments, I rely on three internal checks before every session.
First: What’s my default? What patterns do I automatically bring in—openings, structures, pacing—and are they serving this group or just my comfort zone?
Second: What’s this room asking for? Some groups need energy. Others need stillness.
Third: Who else here holds wisdom? Because I’ve learned that it’s rarely just me.
My go-to rhythm for sessions reflects that approach. I open with a short, story-driven segment—10 minutes or less. I follow that with a written reflection prompt so people can find their own entry point. Then I ask them to gather in triads, not just to talk but to share what surfaced because of what they wrote. That “because of” language changes everything, shifting the energy from discussion to discovery. And finally, I close with a reflection that weaves in the insights I heard.
The result?
A room where everyone contributed, not just the loudest voice.
Learning with People
This approach also has changed how I evaluate my work. Success is no longer applause or perfect transitions. It’s watching people stay engaged without being managed, hearing them continue the conversation without needing me, and getting a message days later saying, “We’re still using what we started that day.” When that happens, I know we did something that mattered.
And here’s the wild part: That usually happens when I get out of the way, when I stop trying to control the flow and instead trust the group to meet the moment. The best sessions aren’t the ones where I nailed the content. They’re where the room leaned in—not to hear what I’d say next, but to explore what they could uncover together. That’s the real work now. Not teaching at people but learning with them.
So before every session, I pause and ask myself the most critical question in my playbook:
What could happen here that couldn’t happen anywhere else?
That question grounds me. It reminds me that the room doesn’t need a sage. It needs a spark, a mirror, and an invitation.
If you’re preparing to lead, consider letting go of what you need to say and starting to listen to what the room is ready to become.
That’s where the real learning begins.
