Leadership shows up when a group of people is standing in a field, waiting to find out whether the day is going to work, and someone decides that it will. I learned that running corporate leadership and team-building programs for national clients. Those leadership lessons for teams followed me from outdoor courses to corporate boardrooms and eventually to the senior leadership team of a fully remote company. The size of the room changes how you lead. The fundamentals change very little.
What Three Hundred Teenagers Taught Me About Structure
One of the projects I am proudest of is a 300-person Amazing Race-style event I designed and led for incoming freshman boys across the 400-acre property at YMCA Camp Kern. At that scale you cannot lead by being everywhere at once. You have to build a structure that leads without you: clear stations, clear instructions, and a bench of team leaders you trust enough to hand real authority to, not just tasks.
That is the first lesson large-scale facilitation teaches. Your job is not to be the smartest or loudest person in the room. Your job is to build something sturdy enough to keep working when you step back from it. A leader who is a single point of failure has built an audience instead of a team.
What Structure Cannot Do
Structure only gets you so far, as I was reminded late that afternoon. Many of the boys had drifted to the lake and were jumping in and out of the water. One of my staff members was trying to get them out for safety reasons. She was doing the right thing, she had a long day behind her, and she was not feeling well, and they were not listening.
A fellow director offered to take a turn. He walked over, said something, and was back about two minutes later with the lake cleared. When she asked how he had done it, he gave a one-line answer I will not reprint here, delivered completely deadpan. We laughed for what felt like twenty minutes.
The joke, of course, was not his technique. What worked was him. He was quiet and unhurried and full of wisdom, and people listened to him without his ever raising his voice. A good structure gets the day running. Calm presence is what carries it when the structure meets a lake full of freshman boys at the end of a long day.
Leadership Looks Different With a Small Group
Not every leadership challenge is a logistics problem. Some of the most demanding work I did was much smaller in scale: multi-day leadership, team-building, and difficult-conversations programs for national clients including P&G and GE.
Small-group leadership asks something different of you. There is nowhere to hide behind logistics. You are in the room with a handful of executives or managers, and the job shifts from building systems to building trust, fast, often with people who have every reason to doubt an outside facilitator.
I learned that early. When I was about 25, a colleague and I flew to Yellowstone to lead a three-day leadership and team-building intensive for a client’s staff. This was long before video calls, so all they knew of us was a voice on the phone. We got off the plane with enormous bags full of supplies for the activities, and they picked us up and took us to our hotel. We ran all three days. On the last night they invited us to their cabin for an evening party, and late in the night they admitted that when we stepped off the plane they had been terrified. We looked like kids, and they had wondered what they had booked. By then they were over the moon about the program and what it had done for their team.
People size you up before you say a word, and you cannot argue them out of it. What you can do is know exactly what outcome you are leading them toward, be honest about the gap between where the group is and where it needs to go, and do the work well enough that the first impression stops mattering. Impact does not wait for a certain age or a certain look.
Leadership Lessons for Teams That Actually Transfer
Across corporate programs, large events, and now a senior leadership role, a handful of skills have shown up everywhere I have led:
- Clarity beats charisma. A team that knows exactly what is being asked of it will outperform a team that is merely inspired but confused.
- Delegate real authority, not just tasks. People rise to the level of trust you actually give them, not the level you say you give them.
- Debrief every time. The learning from an event, a program, or a hard quarter happens in the conversation afterward.
- Read the room before you read the agenda. The plan you walked in with is a starting point, and the room tells you where to take it.
- Calm carries further than volume. The people who get listened to are rarely the loudest ones.
From the Facilitator’s Chair to the Senior Team
At Fortified Data there is no field and no lake. We are a fully remote company, and as Director of People and Strategy, with a scope that spans Culture, HR, and Strategic Growth, I sit on the senior management team. The room I used to read in person now has to be read through conversation. That is how the work began: before I built anything, I asked people directly how they were doing, and what I heard was something no dashboard had captured. The setting changed. The instincts did not: structure that does not depend on any one person, a steady presence when things get loud, and clarity about the outcome. If you are curious what that looks like in practice, the Fortified Data careers page shows the culture we built, from regional meetups to monthly virtual activities that families can join.
Most leaders I have worked with already know what good leadership looks like. The wall comes when the group is tired, the plan is not working, and everyone is watching to see what you do next. That was the moment the director at the lake was ready for, and the moment we faced stepping off that plane in Yellowstone.
Where Leadership Actually Gets Built
Nobody handed the director at the lake a technique. Presence like that gets built the way every leadership skill does: by being in situations that could go wrong, then looking honestly at what happened afterward. That is the step most leadership development skips.
You can start this week. After your next team meeting, take ten minutes and ask three questions: What worked? What did not? What would we change next time? Do it once and it is a conversation. Do it every time and it becomes how your team learns.
Sooner or later every team ends up in its own field, waiting to see whether the day is going to work. The leaders worth following are the ones who have practiced for that moment.
If you would rather build that habit with a facilitator in the room, I design sessions around what your team actually needs, in person or remote. Visit the Facilitation page or get in touch.