How I Design Executive Retreats That Change How a Leadership Team Works

Most executive retreats succeed at the wrong goal. The venue is beautiful, the food is memorable, everyone agrees it was a great few days – and six weeks later the team is working exactly the way it worked before, with better photos.

I understand why it happens. Planning a retreat usually starts with logistics: dates, destination, rooms, meals. Those things matter, and I will get to them. But a retreat is not really a trip. It is one of the few chances a leadership team gets to change how it works, and that change has to be designed on purpose.

That design work is my job as an executive retreat strategist. I am Jeremy Brooks, co-founder and Chief Experience Officer of Strayboots, and I have spent years building experiences for groups from small leadership teams to audiences of thousands. Here is how I approach a retreat that is meant to leave a mark.

Step One: Name the Change Before You Pick the Place

Every retreat brief I take starts with one question: what should be different about this team the Monday after?

Not “what should we cover.” Different answers produce different retreats. A team that needs to make a hard strategic call needs long, protected working sessions and decision rules agreed in advance. A team with new members needs connection built early, before the hard conversations. A team that is performing well but drifting apart needs shared experiences and honest talk about where the drift started.

I push for one primary change and at most two supporting ones. Retreats that try to fix everything fix nothing, because attention is the scarcest resource in the room. Once the change is named, every later decision gets easier: if an agenda item does not serve the change, it does not make the cut.

Step Two: Design the Arc, Not Just the Agenda

An agenda is a list. An arc is a story the team lives through, and people remember stories.

Day one: arrive, connect, open up

Travel makes people tired and slightly guarded, so I never open with the hardest session. The first block should reconnect humans before it challenges executives. A hosted experience early on – something active, a little competitive, a little outside the comfort zone – does more for the next two days than an icebreaker speech ever will. It gives the team a shared win and reminds them they actually like each other.

Then, and only then, I open the real conversation, while energy is high and defenses are down.

The middle: do the hard work in the morning

Deep strategy, conflict and decision-making belong in the morning sessions, when minds are fresh. I protect those blocks fiercely: no phones-as-default, clear questions on the wall, and a facilitator who will name the thing the room is circling without landing on.

Afternoons are for processing and experience: smaller group work, a change of scenery, an activity that lets the morning’s ideas settle. Some of the most valuable retreat conversations I have ever seen happened walking, building or competing – not sitting where the disagreement started.

The close: decide, commit, assign

A retreat that ends with “great discussion” has failed quietly. The final session converts talk into commitments: decisions stated out loud, owners named, first steps dated. I also end with the humans, not the spreadsheet – a closing moment that acknowledges what this team did together, because people carry feelings home more reliably than frameworks.

Step Three: Build Connection Like It Is Infrastructure

Because it is. The strategy work of a retreat runs on trust, and trust runs on knowing each other as people.

I design connection deliberately. Meals are seated with intention, and I rotate them. Shared experiences mix people across the usual alliances. Conversations get prompts that go one level deeper than small talk – interests, stories, the thing you are working on that nobody sees.

My conviction, from years of watching teams, is that human connection comes first. Interests and real conversation tell you more about a colleague than their title and territory ever will, and leadership teams that know each other as people argue better, decide faster and forgive quicker.

This is the same philosophy behind the leadership experiences I design: connection is not the soft part of the program. It is the load-bearing part.

Step Four: Respect the Logistics, Because They Are Messages

Logistics are never neutral. A retreat that preaches rest and reflection while scheduling wall-to-wall sessions from 7 a.m. teaches the team that the words are decoration.

So I plan the practical side like it speaks: travel buffers that respect where people are coming from, rooms with natural light for long sessions, food that fuels rather than sedates, and white space that is actually white. I also plan the failures in advance – weather alternatives for anything outdoors, a backup for every piece of technology the program depends on and a host who can hold the room while a problem gets fixed quietly.

Groups feel the difference between a program that was assembled and one that was hosted. The second kind has someone watching the whole experience, adjusting in real time, the way I do when I host events of every size, from boardroom sessions to gatherings of thousands.

Step Five: Make the Retreat Survive the Flight Home

The highest-risk moment of a retreat is the week after. Inboxes are full, old habits are waiting and the agreements made around a fire pit start to feel far away.

So I build the bridge back before the retreat ends. Decisions and commitments get captured in plain language, shared within a day. Each commitment gets an early checkpoint, close enough that momentum is still warm. And the team names one ritual – a short recurring conversation, a standing question, a monthly review of the retreat’s decisions – that keeps the thread alive without another plane ticket.

You can see how programs built this way play out in practice in my case studies.

Frequently Asked Questions

How long should an executive retreat be?

Two full days is the sweet spot for most leadership teams: enough time to get past politeness and into real work, short enough that energy and attendance hold. One day works for a focused decision. Three days earns its keep only when the agenda truly needs the depth – otherwise day three becomes an expensive echo of day two.

Should the CEO facilitate their own retreat?

Almost never the whole thing. The senior leader’s voice carries weight even when they try to make it light, and the team reads their reactions instead of thinking freely. An outside strategist and facilitator frees the leader to participate honestly – and lets someone else be the one who interrupts, redirects and protects the quieter voices.

What is the biggest mistake teams make planning a retreat?

Starting with the destination. A stunning location cannot rescue a retreat with no named purpose, and a modest location works beautifully when the design is right. Decide what must change, design the arc, then choose the place that serves both.