16 Sep Inside a Six-Day leadership retreat Between Italy and France
How trading the boardroom for the trail led to one leadership team finding more honest conversation than a year of meetings.
Eight people. Six days. Two countries of trail between them. One leadership retreat with a difference.
Last spring we hosted the top tier of leadership team from a large, US-based company with offices scattered across the world. This team is usually only together for one hour a quarter, on a screen, with an agenda. We built them a week with no agenda at all, and watched it become the most useful week of their year.
Nine months to build one week
The CEO chose who came. That decision alone took months — who this trip was actually for and who the team would become once these eight people were standing on the same mountain.
From there came nine months of planning. We aligned calendars across time zones, built an itinerary around the specific rhythm this group needed, and quietly handled every detail. This work meant that once the group landed, nothing about the week felt engineered. That is the part people don’t see: the ease of a week like this is the most expensive thing about it.
Six days, two countries, a different conversation every day
The days on the leadership retreat were built around hiking — trails threading between Italy and France, with the group moving as one but the pairings changing constantly. Some mornings it was two people who’d never worked closely together, walking three hours and talking the whole way. Other days it was four or five, trading stories about a project from a decade ago. Nobody assigned the pairings. The trail did that on its own.
What struck us was how much real conversation happened without anyone trying to make it happen. No facilitator, no icebreaker, no forced sharing circle. Just eight senior people, a changing landscape, and enough hours in a day for a conversation to actually finish.
Not everyone in the group knew each other before this trip. What we noticed, and genuinely admired, was how the stronger hikers looked after the less strong ones — staying back with the group, matching their pace, no hint of judgment about it. Only once everyone was settled would they stride ahead to finish the day’s route at their own speed. Nobody asked them to do that. It was just quiet consideration, from people who barely knew each other three days earlier.
Where the real work happened
The work conversations didn’t happen in a conference room, because there wasn’t one. They happened over breakfast, planning the day. They also happened at long lunch tables halfway up a mountain, over cocktails before dinner, and again at dinner.
None of it was scheduled as ‘work time.’ All of it was work — the honest kind, the kind that happens when people are relaxed, tired in the right way, and not checking a phone under the table.
What surprised us
Despite planning these weeks for a living this one still surprised us. We expected the scenery to be the highlight as it was genuinely some of the best trail in Europe, the kind of view that stops a conversation entirely for a minute. But what stayed with us afterward was how much this group opened up. The hikes were a highlight. The lunches were a highlight. The dinners were a highlight. By day six, this wasn’t eight executives who happened to work at the same company anymore.
Would this work for your team?
We think this format is one of the most effective things a leadership team can do for morale, trust and authentic working relationships. Daily hiking, changing pairings, real landscape and no agenda forcing the conversation. It isn’t a team-building exercise. Nobody was asked to trust-fall. It’s simply what happens when a group of smart, driven people are given a week, a mountain, and no reason to perform.
If your leadership team is overdue real time together, the process starts the same way this one did. A conversation about who your team is, and nine months (give or take) to build the week around them.
Regards from the mountains,
Danielle
In their words
“You are a master at curating a trip for the group, from the appropriate level of hiking for each individual, to planning different fun and delicious lunches and dinners each day, to building in time for rest and shopping, to being fun and easy to be around. The experience could not have been easier or more wonderful for our group, thanks to your attention to detail so that all our needs were not only met but exceeded. Can’t thank you enough!”
— A guest from the trip