This is going to be a disaster.

That was an actual thought I had before walking into a recent workshop.

Looking at the prep materials, sitting through the planning sessions, reviewing the agenda: everything felt overwhelming. The scope was massive. The timeline was tight. There were too many objectives packed into too little time.

How is any of this going to work? I kept wondering.

I’ve been doing this work for years, but this was one of the first times I genuinely doubted whether a session could succeed. Walking into that room, I was nervous in a way I hadn’t felt in a long time.

And I was completely wrong about what would make or break that day.

When Preparation Meets Reality

I was working with a facilitator I’ve collaborated with 33 times since August 2022. Yes, I counted. We’ve been through easy sessions and challenging ones, but this felt different.

The agenda was packed. Multiple complex topics. Tight deadlines. Materials scattered across slides, handouts, and wall displays. Everything about the setup screamed potential chaos.

But then people started walking into the room.

Handshakes turned into embraces.

Old colleagues caught up on inside jokes.

There was genuine laughter, the kind that happens when people actually know and like each other.

And my collaborator moved through it all seamlessly, greeting people by name, asking about specific projects.

I watched her read the room in real time, adjusting energy and expectations based on the actual humans in front of her rather than the agenda in her hands.

As the session began, I realized something I’d completely missed: the value of rapport. These people had history together. They trusted each other. And they trusted her to guide them through whatever challenges lay ahead.

I’d been so focused on whether the agenda would work that I’d forgotten the most important ingredient wasn’t in the materials at all.

It was already in the room.

The Thing Slides Can’t Do

What makes the difference when everything else feels impossible?

It’s not perfect preparation. It’s not flawless materials or airtight timelines.

It’s the facilitator who understands an audience so deeply that she can navigate any agenda. It’s participants who trust each other enough to tackle difficult topics. It’s the kind of human connection that makes people willing to do hard work together.

Rapport enables conversations that would otherwise be too risky. It creates space for complexity that rigid structures can’t accommodate.

I’d been getting lost in the slides when I should have been getting lost in the possibilities. Because when you have the right people in the room who genuinely understand each other, almost anything becomes workable.

The agenda didn’t save that workshop. The relationships did.

Rapport Is Code for Understanding

Rapport isn’t just about being likable or charming. It’s code for: I understand my audience deeply.

When you truly know the people in your room, everything changes. You can deliver difficult news because you understand how they process information. You can push on sensitive topics because you’ve earned the trust to do so.

The practical elements aren’t complicated: knowing people’s names, understanding their fears, being sincerely generous with your attention. It’s asking about the project that kept them up last night, remembering the challenge they mentioned six months ago.

I try it in my own workshop work, too. When I’m drawing, I’m listening for the hesitation in someone’s voice, watching for the moment when an idea clicks, noticing who’s engaged and who’s checked out.

Some facilitators play it safe, delivering the same slides they’ve scrolled through a hundred times. But the best ones read the room and adjust in real time, in my opinion.

Human connection gives you advantages that no screen, no slide deck, no digital tool can replicate.

Building Better Rooms

These aren’t super high-level, special professional skills. They’re traits we can all access.

Start simple: learn people’s names and use them. Ask about the work that’s keeping them busy. Listen for the worries, not just what’s on the agenda.

Spend a few minutes thinking about the humans who’ll be in the room rather than the content you need to cover. What are their current challenges? How can you create space for real conversation instead of just information transfer?

You can be the person who shifts the energy in the room. You can turn a routine meeting into something that actually moves work forward.

After 33 sessions with that facilitator, I’m still learning how much difference it makes when someone shows up prepared to connect with people, not just present to them.

The best meetings aren’t about perfect presentations. They’re about imperfect humans doing important work together.

Grateful you are here,

Wade