The Key to a Great Off-Site

Hi Reader,

It's that time of year when many Executive Teams are planning their end-of-year retreats.

If you're being honest, you probably have mixed emotions about off-sites. You'd be in good company if you've wondered about their effectiveness.

When designed well, there is certainly something powerful about a great Executive Team retreat. You have the opportunity to step back, think strategically, reconnect with the team, and work through important questions that rarely receive enough attention during the normal workweek.

As a result, the team can leave feeling more connected, aligned around a clearer shared direction, and excited about what they can accomplish together.

But then Monday arrives. The inbox is overflowing, and urgent issues are waiting, perhaps even more than normal because they've stacked up while you were at the retreat. Everyone returns to their functional responsibilities, and familiar patterns begin to take over.

A few weeks later, much of the energy has faded. And sometimes, despite the meaningful conversations and commitments made, very little has actually changed.

Self-awareness matters.

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The Mountaintop Experience

There's a reason we sometimes describe these gatherings as mountaintop experiences.

Stepping away from our normal environment gives us a different perspective. We see things more clearly, connect more deeply, and imagine possibilities that are harder to recognize when we're immersed in the day-to-day. They're also referred to as mountaintop experiences because real breakthroughs can occur, similar to the feeling of accomplishment that comes from summiting an incredibly challenging peak at the end of a long hike.

The problem is that the view from the mountaintop isn't the same as living in the valley.

In a Harvard Business Review article titled Off-Sites That Work, Bob Frisch and Logan Chandler explored this challenge. Drawing on their experience with executive teams, they observed that surprisingly few teams could point to meaningful changes in how their organizations operated as a result of their off-sites.

The retreat may have been excellent. The conversations were honest, and the new strategies discussed probably felt energizing.

But the environment they returned to hadn't changed.

The same meeting rhythms still exist. The same systems that lead to competing priorities are still there. The same habits of communication and decision-making haven't changed.

A great retreat can change how a team feels. But lasting transformation requires changing how the team works. That takes more than a great experience together.

Three Ways to Bring the Mountaintop Home

If you're planning an Executive Team retreat, we'd encourage you to think beyond what you want the team to experience during those days together. Consider what you want to be different when everyone returns.

1. Turn Insights Into New Team Behaviors

Retreats often result in excitement about an emerging vision. When the team focuses on improving how they collaborate, they can also produce great insights about how to work better with one another. But if some of the time isn't spent discussing and making agreements about how to carry out the new vision and make changes to the way you collaborate, there's a significant chance that very little will actually change.

To combat this reality, teams should ask a question like this before leaving:

What will we actually do differently when we're back together next week?

It could look like committing to a first small bet related to a bigger vision and establishing a way to track progress throughout the next quarter. Maybe the team commits to naming tension earlier rather than allowing frustration to build. Maybe it agrees to make certain decisions collectively instead of within functional silos. Or perhaps it decides to begin each Executive Team Meeting by reviewing shared priorities.

The goal isn't a long list of improvements. It's identifying a few meaningful behaviors the team is willing to practice consistently.

2. Build Those Commitments Into Your Regular Rhythms

One of the biggest mistakes teams make is assuming that because something was discussed and agreed upon at a retreat, it will naturally become part of how they operate. Remember the quote from Atomic Habits: "We don't rise to the level of our goals, we fall to the level of our systems."

Good intentions get crowded out by familiar habits, and the quicker we accept this, the more likely we are to identify our broken ways of working and start fixing them.

If your team commits to greater accountability, establish a consistent practice of reviewing commitments and action items. If you want better strategic alignment, make time in your weekly Executive Team Meeting to monitor progress and work through strategic priorities.

And if you want to become a team that learns and improves together, make reflection part of your regular operating rhythm.

If something matters enough to commit to at the retreat, it should matter enough to make room for in your regular work.

3. Schedule a Retrospective Before You Leave

This might be the simplest and most valuable practice of the three.

Before the retreat ends, put a follow-up conversation on the calendar for 60 to 90 days later.

Not another off-site, just an opportunity to revisit what the team committed to and assess how things are going.

Ask yourselves:

What have we actually changed since the retreat?
What's working, and where have we slipped back into old habits?
What adjustments do we need to make?

This practice reinforces an important mindset: improvement isn't something we accomplish at a retreat. It's something we continue working toward together.

Some new practices will work beautifully, while others will need adjustment. That's not failure. That's what learning and growing together as a team looks like.

And the more consistently a team reflects and adjusts, the less dependent it becomes on occasional mountaintop experiences to improve.

A Final Thought

We love a great Executive Team retreat. Some of the most meaningful moments we've experienced with teams have happened when they've stepped away from their regular responsibilities and created space for honest conversations, deeper connection, and strategic thinking.

I wouldn't trade those experiences for anything. But we've also learned that the success of a retreat isn't best measured by how people feel when they leave.

It's measured by what's different 90 days later.

-Shaun & Joe

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