FOUR Elements of a Successful Leadership Retreat
A leadership retreat that really works is one where hard decisions get made, important conversations happen, and people leave with more understanding of each other than they had when they arrived, plus a clear sense of where the company's going and what they need to do next.
Getting out of your everyday environment does something to how you think. Away from the usual routines and the usual solutions, it gets easier to imagine new approaches and see things you may have been missing. Freeing yourself from the constant interruptions and pressures of daily work allows you to slow down and concentrate better so you can come up with fresh ideas.
Add in the rest of the team, who go through the same refreshing changes, and that's when the magic happens — people connect, find answers together, and come away with a deeper understanding of how all the pieces fit together.
Here’s what makes a leadership retreat work
1. Choose a place with no distractions
A beautiful hotel with a spa, pool, bar and golf course sounds perfect as a reward for a job well done. But if you want to get a real product at the end of your retreat, don't book it at a place that will compete with you for people's attention. If the goal is alignment, sorting out issues, or getting next year's planning done, choose a setting that is relaxed and pleasant, but doesn't offer easy exits from the group. You don't want people taking off for the bar and missing the intimate conversations after a hard day's work or running off for a massage appointment in the middle of an important brainstorm.
2. Design activities the whole team does together
Offering a menu of free-time activities seems generous, but it fragments the group — and that's often at odds with what you're trying to accomplish on this retreat.
Most often, the retreats that move the needle are built around shared experience. Everyone hikes the same trail. Everyone sits around the same fire for the evening conversation. Everyone works through the same planning session, together, in the same room. That shared time can be even more important than the structured agenda. It's often the walk to breakfast, or the conversation after dinner, where the real breakthroughs happen. They happen by chance — so be sure to create the conditions for that by keeping the group together instead of letting it splinter.
In creating the agenda of shared activities, make sure to allow for enough time for people to slow down and adjust to the new pace. The day of travel can be exhausting, and the emails are still flying around as the business winds down. Make sure that the retreat isn’t ending just as the good stuff starts flowing. Two days is probably just a little too short.
3. Keep the group small enough to actually connect
A leadership retreat isn't a company-wide event. The dynamics that make it valuable — candor, trust, the ability to actually hash something out — depend on a group small enough that everyone is part of the same conversation. Somewhere in the range of 15 to 25 people tends to be the sweet spot: big enough to have real diversity of perspective, small enough that no one can be forgotten.
Breaking into intimate groups of 3 to 5 people is a good idea. It can help to build or strengthen a relationship that opens doors. Build these into the agenda at some point during the retreat.
4. Hire a coordinator
Even though you may set the agenda, and even though your personal assistant may be a cracker jack who'd like to go along, it's often good to hire a coordinator or assistant from outside the company to take care of logistics both in the lead up to your retreat and onsite. Having no history with the attendees makes it run more smoothly and fairly. No one has to be bogged down with the little things and yet the little things are taken care of.
Why The Perch is just the right place for this
The Perch sits on 4 private acres in the San Bernardino Mountains, less than 2 hours east of LA, near Lake Arrowhead — twelve cabins, tucked into the trees, with nothing around to pull people away from each other. No spa. No bar. No golf course. Instead, it offers quiet, space to think, and a setting where the thing to do is be together — hike together, eat together, sit by the fire together, and most importantly, have those conversations where the most meaningful work gets done.
It's built for exactly the kind of retreat described above: a leadership team of roughly 15 to 25 people, with several gathering spaces for the group to connect, reflect and engage. When it's time to step away from the table for a break, there's plenty to do as a group — outdoor activities like yoga, forest bathing, a boxed lunch, even a boat tour on the Arrowhead Queen.
Contact events@theperchattwinpeaks.com to talk about what you need for your upcoming retreat to make it productive and memorable.
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