Next week I’m co-leading a retreat in Jackson Hole for more than 50 founders. As I prepare, I’ve been reflecting on what a decade of group work has taught me. That includes leading Downshift and men’s retreats, and participating in twelve-step meetings, men’s groups, and more trainings and retreats than I want to admit.

Most of my coaching has been one-on-one, but I love the connection and perspective I receive from group work. With a new venture launching this fall, I want it to be a bigger part of my practice in the coming years.

In one-on-one work, I’m aware of my own experience, tracking and staying in contact with the person across from me, and noticing what’s emerging between us. Group work has more layers. Alongside my own experience, I’m attending to each participant, what’s happening between them, the group as a whole, and the dynamic within the facilitation team. That complexity is what draws me to this work.

As I do more group work, I’m learning to attend to these different layers of relationality and sense what’s needed in each. Here’s how I currently think about them, what I’m noticing, and the questions I’m bringing to my practice.

With myself

What’s happening within me as I sit with the group? What am I feeling, and what do I want to say or do? Staying in contact with my thoughts, emotions, and bodily sensations helps me notice how my own experience is shaping the way I guide. From there, I can consider what might serve the group and what I need to work through myself. Would sharing what I’m noticing help us explore something, or would it pull attention away from what needs space?

With the participant

What’s happening for this person, and how are they relating to what’s unfolding in the group? What are they saying, and what might be going unspoken? I’m attending to their words, tone, posture, and how they participate, including moments when they lean in, pull back, or go quiet. A shift gives me something to be curious about and perhaps contact, without assuming I know what it means. Staying attentive helps me consider whether to check in, offer an invitation, or give them space to participate in their own way.

With the group

What’s the overall mood in the room, and how are people relating to one another? Is there enough trust for people to speak honestly, disagree, and ask for support? I’m attending to the emotional tone, shared themes, and patterns of participation, especially how people respond when someone shares something vulnerable or expresses a difference. Those responses give me clues about what the group is making room for and what feels challenging to bring forward. That helps me consider whether naming a tension or inviting the group to reflect on a pattern would help us work with it together.

With the facilitators

What’s happening between us as we guide? Are we in sync, and am I trusting how another guide is leading? Together, we’re feeling our way with a particular group, making eye contact, picking up on subtle signals, and making room for one another. Sometimes that means stepping back and letting another facilitator follow something I don’t yet see. Other times, it means finding a skillful way to interject and offering that same openness when I’m leading. We’re sharing responsibility for the room, trusting one another to step forward or make space depending on what the group needs.

To cultivate this relational awareness, I often focus on one dimension at a time. I might stay with my own experience for a while, then turn toward an individual or widen my attention to the group. The more familiar I become with each, the more naturally I can move between them while remaining aware of all four.

The deeper I get into this work, the more I appreciate how intertwined these dimensions are. What’s happening in one can be felt in the others. I’m part of that too, shaping the room and being shaped by it.

Next week, our team will work with large and small groups, each with its own personalities and dynamics. I’m excited to guide alongside my new partners as we discover how we hold space together and learn from each other. We get to keep refining the craft and have fun doing work we love.