We need to talk.

What I mean is that, in general, people need to talk more. Sure, we talk to each other — we’re often beleaguered by meetings. And your meetings might be productive — you’re knocking down problems left and right, sure, but what happens when we need to do deeper work? What happens when we need to think about stuff that defines who we are? We’re talking branding, messaging, our vision for the future. Doing that yourself can feel like performing an appendectomy on yourself, and just as successful.

That’s where facilitation comes into play. Sometimes you need a third party to come in and lead the discussion. We love doing this work because it means creating spaces where genuine dialogue can flourish. We don’t want to create by committee — the trick is being able to surface really creative ideas in a collective environment. 

Starting with Vulnerability

How we get started with a facilitated session can determine how everything else unfolds. We like to start out with an icebreaker that invites genuine vulnerability. When participants share something real about themselves — perhaps a challenge they're facing or an unexpected joy in their work — it creates ripples of authenticity throughout the room.

Everyone has to participate in this kind of thing. One of the biggest challenges in these sessions is that person sitting back in their chair with arms folded.

When a participant shares something genuine, they're silently telling others, "It's safe to be real here." I often start with a simple but meaningful question: "What's something in your professional life that you're still figuring out?" This question works because it acknowledges that we're all works in progress, regardless of our position or experience.

The size of your group will naturally influence your approach. For smaller groups (under 12), you might have everyone share in a circle. For larger groups, consider breaking into pairs or triads, allowing for more intimate sharing before bringing key themes back to the whole group.

Other ideas are to ask people to share a failure they’ve faced in their work or something that they were surprised by, or a moment where they were forced to disentangle their professional identity from their personal identity. All of these work really well.

When a participant shares something genuine, they're silently telling others, "It's safe to be real here."

The activity, however, is only one piece of this work. Another crucial aspect is your vulnerability as the facilitator. You have to model this. You might have to go first. Either way, you need to bring excitement and enthusiasm to the session. Being sardonic or cynical won’t work. You can be funny and disarming and self-deprecating, yes — but be sincere. Don’t deprecate the work that’s being done in the room.

A quick note about people: They’re all different. One thing we always keep in mind is that some people face real challenges. They’re not just throwing up roadblocks because of some imagined slight or because they have a feud with Larry in Accounting. Some people have disabilities that can make a session like this challenging. Some people are facing personal situations that are too distracting for them to be present. We like to surface those issues before the session, but if we can’t, we like to keep an eye out for folks that seem to be having a hard time, and to adjust in the moment.

Collaborative Goal-Setting

The vulnerability work we do at the outset creates safety, and what’s next is just as important. Everyone needs to agree on why they’re there. This work also helps to build energy in the room. Now that everyone is bought into the session emotionally, it’s time to get together on the goals of the room.

You can ask, "What would make this time together truly valuable for you?" This simple question transforms participants from passive attendees into active participants in the session's success.

We document the goals where everyone can see, so we can always go back to them if we get pulled off track. We take a moment to gather expectations from everyone, and then we agree on where we’re all heading.

Keeping the Energy Alive

Human attention is rhythmic. I structure sessions with this in mind, changing activities or approaches every 30 minutes or so. A little longer might be fine, but it’s easy to stay on task and still switch things up. Obviously, if things are flowing, feel free to switch it up in the moment, but you can shift from individual reflection to pair discussions, or from analytical tasks to creative exercises.

Visual tools, particularly Post-it notes, are invaluable allies in facilitation. They democratize participation by allowing everyone to contribute simultaneously and create a tangible record of the group's thinking. More importantly, they help transform abstract discussions into concrete action points. Even if you’re working online, sticky notes will be your friend. We work in Figma, especially their whiteboard product called FigJam, using virtual sticky notes to get people following along. They might not be able to write notes and put them on the wall, but they can be invited to add something verbally and request something be moved. Just make the invitation. This isn’t a one-way conversation.

I always emphasize that there are no "dumb" questions. In fact, I encourage participants to voice their uncertainties, as these moments often lead to the most valuable clarifications and insights.

Reading the Room

Every organization has a unique culture, and successful facilitation means listening carefully and paying attention to what’s going on. This is one of the reasons why we like to do in-person facilitation sessions, where possible. We can read body language, notice unspoken hierarchies and relationships. These patterns influence how people interact. It’s not really about potential conflicts. Most organizations are also really good at being in stasis and not at risk of bursting out into open conflict. The thing we’re looking for is if someone in the room is withholding — we start with the assumption that everyone has something important to contribute. If they’re withholding, it means they don’t feel safe, and that’s usually something going on in the group dynamic. We can work with that.

This might mean that we don’t rely on volunteers. We might have to go around the room, or rely on people to do some heads down work or work in groups. So much depends upon the moment.

When conflicts arise — and they often do in productive sessions — I view them as opportunities rather than obstacles. The key is creating an environment where differing opinions can be expressed respectfully and explored constructively. Sometimes, the most valuable outcomes emerge from working through disagreements thoughtfully.

When conflicts arise — and they often do in productive sessions — I view them as opportunities rather than obstacles. The key is creating an environment where differing opinions can be expressed respectfully and explored constructively.

Closing the Loop

The end of a session is just as crucial as its beginning. I always ensure there's clarity about what happens next — whether that's a follow-up meeting, a summary report, or understanding how the session's outcomes fit into broader organizational initiatives.

Context is key. Participants should leave understanding not just what was decided, but why it matters. This might mean explicitly connecting session outcomes to organizational goals or highlighting how their contributions will influence future decisions.

Facilitation requires a genuine belief in the power of bringing people together to create meaningful change.

We’d love to show you how we do it, give you some pointers, or run a session. Just let us know how we can help!