Designing Our Retreat the Way We Ask Our Clients To
We spend a lot of time helping organizations design retreats, offsites, and leadership experiences. We ask clients to slow down, get clear on purpose, and make deliberate choices about how they use the limited time they have together. We talk often about intention, tradeoffs, and the difference between experiences that feel productive in the moment and those that actually create momentum afterward.
When it came time to plan our own annual leadership retreat, we knew those same standards applied. Not because we needed to demonstrate anything, but because the principles we encourage others to use are the very things that prevent retreats from becoming overpacked, exhausting, or ultimately forgettable. The goal was never to create a perfect retreat. The goal was to design one that did what it needed to do for the organization and the people in it.
So before we talked about topics, outcomes, or activities, we asked a simpler and more consequential question: what does this retreat actually need to do?
That question shaped every decision that followed.
Starting with time instead of topics
One of the most common patterns we see when teams plan retreats is starting with content. Leaders list everything they want to discuss, everything that feels urgent, and everything that did not quite fit into regular meetings during the year. The intention is good, but the result is often an agenda that tries to do too much and ends up doing very little well.
We intentionally started somewhere less exciting but far more clarifying: time.
We calculated the actual number of hours we would have together. Not idealized hours. Not “best case scenario” hours. Real, bounded time that accounted for travel, energy, and the reality that people are not at their best for eight straight hours simply because the calendar says they should be. That number became our primary constraint, and it forced a level of discipline that no brainstorming session ever could.
From there, we framed the retreat around three purposes rather than a list of topics: looking back, looking forward, and looking at each other. The last bucket of time still feels funny to say out loud. We debated it, laughed about it, and briefly tried to make it sound more polished. We ultimately kept it because it did exactly what we needed it to do. It created a shared mental model for why we were together and gave us a simple way to test whether something truly belonged in the room.
We landed on a structure that devoted roughly 10% of our time to looking back, 60% to looking forward, and 30% to looking at each other. That breakdown became the backbone of the retreat design. It guided decisions about what deserved in-person attention, what could happen asynchronously, and what simply didn’t rise to the level of retreat-worthy. Practically, this meant putting the retreat into a spreadsheet before it ever became an agenda. We mapped the total number of hours we would actually have together and then worked backward, accounting for transitions, breaks, and travel fatigue. Seeing the time laid out this way changed the conversation quickly. It made tradeoffs visible and forced us to confront how much we were implicitly asking the retreat to carry.
The smallest portion, looking back, was about closure. It was enough time to reflect intentionally without letting the past dominate the future. The largest portion, looking forward, reflected where the organization needed shared clarity and alignment. The remaining time, looking at each other, was deliberately set aside for team development. That time was spent getting to know one another beyond roles and titles, engaging as people, and building the relationships that make working together sustainable. It included shared meals, informal conversations, moments of fun, and a collective experience outside a conference room, including an escape room, that required collaboration, communication, and trust in a different way than day-to-day work allows.
Once the framing was set, we assigned weight to each purpose. Not because percentages are inherently meaningful, but because they make priorities visible and tradeoffs unavoidable. This structure also gave us permission to say no. When an idea did not clearly support one of those three purposes, it became easier to move it out of the retreat without second-guessing ourselves. That framing became more than a way to describe the retreat. It became a test. When we debated whether something belonged, we asked which bucket it served and what it would displace. If an item could not clearly answer that question, it usually didn’t belong in the room. This was especially helpful when everything felt important, which is often the case when teams finally have uninterrupted time together. The percentages were not meant to be precise, but they were intentionally constraining. They gave us a boundary for decision-making. If we found ourselves creeping beyond thirty percent of time spent “looking at each other,” for example, it prompted a real conversation about whether we were avoiding harder strategic work or whether the relational investment was truly what the organization needed in that moment.
Protecting the retreat with a clear decision filter
After the structure came the filter. Every potential item was sorted into one of three categories: must happen during the retreat, would be helpful if time allowed, or could happen before or after.
This step mattered more than any individual agenda choice. It forced us to distinguish between what was important and what was important enough to justify being in the room together. Some conversations were valuable, but not valuable enough to take time away from deeper alignment. Others benefited from thoughtful input, but not necessarily synchronous discussion.
For many teams, especially those that are not together regularly, there is a temptation to treat a retreat as the place where everything must happen. In practice, that usually leads to cognitive overload and diluted focus. We intentionally moved certain work into pre-retreat deep dives and post-retreat follow-ups so that the time together could remain centered on clarity, connection, and forward momentum. This looked like not doing a full-year financial report at the retreat, but doing that two weeks ahead of time, so we could marinate on that information and come to the retreat ready to strategize around that information. Other things were included because of necessity - for instance, we had to record a video with all of us that wouldn’t normally be something we felt rose to the level of being included in the retreat but was the only time we would all be in the same space together.
Designing for context, not assumptions
Like many modern organizations, we do not spend most days working side by side in the same physical space. When we are together, it is often for client visits that are non-stop rather than internal reflection. That reality influenced how we thought about pacing, priorities, and what truly benefited from being face-to-face.
This did not make the retreat more complicated. It made the design more intentional.
Teams that see each other every day often use retreats as a pause from routine. Teams that are rarely together experience retreats as concentrated moments of shared work. Those contexts require different design decisions, even when the underlying framework remains the same. The broader lesson is not about remote work specifically. It is about designing retreats based on how people actually work rather than how we assume they work.
For us, that showed up in choices like protecting morning energy for the more complex conversations, being more selective about what we scheduled late in the day, and resisting the urge to treat evenings as an extension of the workday. Those decisions would look different for a team that works together daily, but the underlying question is the same: when are people most able to think clearly, engage honestly, and contribute well?
Letting feedback shape real change
Another decision influenced this retreat well before anyone arrived: we used feedback from the previous year, and we treated it as actionable data rather than a formality.
After our last retreat, we asked our team what supported their energy, connection, and clarity, and what undermined it. We utilized a simple exercise of start, stop and continue. We looked back at that information for patterns rather than individual preferences, and we made different decisions this year as a result. That included adjusting pacing, being more realistic about energy, and acknowledging that intensity is not the same thing as effectiveness. We realized staying up too late last year meant we weren’t starting off the next day on our best foot. Importantly, we reviewed that feedback early in the planning process, not a week before the retreat, so it could genuinely influence structure, pacing, and priorities rather than being retrofitted after decisions were already made.
It is easy to collect feedback. It is harder to let it meaningfully change how something is designed. Doing so required us to revisit assumptions and adjust elements that technically “worked” but did not serve people as well as they could have.
Why the details matter
Not every design choice was structural. Some were small, practical decisions that would be easy to overlook. But those choices matter because they communicate care. They signal whether people’s time and energy are being respected and whether the experience was thoughtfully designed or assembled at the last minute.
In our experience, retreats succeed or fail less because of any single activity and more because of whether the details align with the stated intentions. When they do, people feel it. When they do not, even well-chosen content struggles to land.
The work beneath the work
From the outside, a well-designed retreat can look effortless. What is invisible is the thinking underneath. The time calculations. The prioritization conversations. The discipline to say no. The willingness to move good ideas out of the room to protect better ones.
That hidden work is not incidental. It is the work.
Designing our own retreat required the same level of intention we bring to our work with organizations across sectors. Not because we needed to demonstrate expertise, but because thoughtful design is what turns time together into clarity, alignment, and momentum rather than exhaustion.
A different way to think about retreats
If there is one takeaway we would offer to leaders planning their own retreats, it is this: effective retreats are not about covering more ground. They are about making deliberate choices with limited, valuable time.
Stepping back, what became clear is that retreats are not primarily agenda problems. They are design problems. How time is framed, what constraints are honored, and which decisions are made visible often matter more than any single topic discussed. When those elements are thoughtfully designed, the retreat does far more work than the agenda alone ever could.
When retreats are approached this way, they stop being events you get through and start becoming moments that genuinely move the organization forward. And if that perspective resonates, it may be worth reconsidering not just what your next retreat includes, but how it is being designed to serve both the people and the work ahead.
If you’re thinking about an upcoming retreat or offsite and want support designing it with this level of intention, this is the kind of work we partner with organizations to do. Thoughtful design can make the difference between a retreat that feels busy and one that actually moves the work forward.
