I get asked to facilitate retreats pretty often. And a lot of the time, my first response isn’t “yes” or “no.” It’s a question.
What do you want to be different when everyone gets back to the office?
That question usually changes the conversation.
Because here’s what I’ve watched happen over and over again. A team spends a day or two offsite. There’s real energy in the room. Good conversations happen. People feel reconnected to each other and to the mission. They leave with a list of action items and a shared sense of direction.
Then Monday arrives. The inbox is full. The calendar is stacked back-to-back. And within a few days or weeks, the only thing anyone clearly remembers from the retreat is that one icebreaker that got a little awkward. Oh, and that somewhere in their notes is a list of ideas and actions they committed to — if they can find it again.
That’s not a failure of the retreat. It’s a failure to plan for what comes after it.
There’s real value in getting out of the building
A well-designed retreat does things that are genuinely hard to do any other way. Getting a team out of the office creates space for conversations that never make it onto the regular meeting agenda. You’re not watching your clock and mentally preparing for your next meeting while you’re in this one. That new email can wait until later. Nobody’s knocking on the conference room door because they saw you walk in. People from different parts of the organization are actually in the same room, talking across the boundaries that day-to-day work tends to reinforce.
That’s worth something. Culture conversations, trust-building, and planning all benefit from dedicated blocks of time without interruption. You can’t cram those into a 45-minute staff meeting between two other meetings.
So I’m not here to talk you out of a retreat. I’m here to make sure that the retreat and what comes after it give you the outcomes you’re looking for.
Why one day usually isn’t enough on its own
Change doesn’t happen in a single session. It happens through repetition — trying something new, seeing how it lands, adjusting, and trying again. This is especially true for culture work. If you want to shift how people communicate, how decisions get made, or how conflict gets handled, you’re not asking people to learn a new fact. You’re asking them to change behavior. And behavior change takes time. It takes practice and repetition. It needs someone willing to keep coming back to it after the retreat energy has faded.
One of the leaders I interviewed for my 2025 Nonprofit Culture Pulse research said it plainly: “It’s not something where one day you wake up and say, ‘We’re going to change this culture.’ The hard part is actually applying it.”
That’s exactly right. The easy part is naming the problem and agreeing that something needs to change. The hard part is doing something different, consistently, until it becomes the new normal.
A retreat can be a powerful starting point.
It’s rarely sufficient on its own.
What tends to work better
I’ve facilitated many retreats over the years. The ones that actually lead to change share one thing in common: they don’t end when everyone heads home.
The retreat that didn’t stick
One client came to me wanting a retreat focused on team building and annual planning. Their teams were working in silos, collaboration was breaking down, and frustration was building up. We partnered on a solid two-day retreat — surfaced real issues, rebuilt some trust, explored how they could make decisions and work across team boundaries differently. They left with energy and a clear action plan. When I recommended three follow-up sessions keep the energy going, revisit commitments, and reinforce the learning, they declined, preferring to take it from there on their own.
About two months later, I checked in with the Executive Director. Not much had changed. The silos were still there. Teams still weren’t really collaborating. The action plan hadn’t really gone anywhere.
The retreat that stuck
A different client came to me with almost the same situation. Similar frustrations, same goals, same ask for a retreat. This time, when I recommended we add three follow-up sessions over the two months after the retreat — time to revisit the action plans, reinforce the ideas and connections from the retreat, talk honestly about what was improving and what wasn’t, and figure out together what would actually move things forward, they agreed.
Two months after our final session, I reached out. The difference was striking. Staff were actively reaching out to other teams for help and collaboration — something that hadn’t been happening before. They had taken the meeting norms we worked on together, built them out further on their own, and posted them in their conference room. Stories came back about how they were approaching conversations differently — more directly, less avoidant. The work had become their own.
That’s not an isolated example.
The pattern I keep seeing
When I look back across the one-off retreats and workshops I’ve facilitated over the years, nearly all of those clients reported little meaningful change afterward. The clients who worked with me across multiple sessions, with time to practice, adjust, and put ideas into actual daily use, are the ones who come back with stories of real progress. Not just about what they learned, but about what they started doing differently. That pattern has been consistent enough to change how I work. (If you want to go deeper on why training so rarely sticks on its own, I wrote about that here: How to Make Training Stick — Just Like in the Olympics.)
What happens between sessions matters as much, if not more, than the sessions themselves. What are leaders modeling back at the office? What conversations are happening, or not happening? That’s where culture actually lives — not in the retreat room, but in the everyday moments that follow it.
Why an outside perspective helps
Even with the best intentions, it’s hard to see your own patterns clearly. You’re inside them. That’s where an outside facilitator adds real value, not just to run a good agenda, but to notice what the team can’t see about itself. To ask the question that feels too risky coming from the inside. To help leaders connect the dots between what they say they want and what’s actually happening.
This is especially useful if you’re a newer leader trying to get a clear picture of what you’ve walked into, or if you’ve tried to change something before and it didn’t stick and you’re trying to figure out why.
Before you schedule your next retreat
Ask yourself: what do you actually want to be different six months or a year from now? If you can answer that clearly, you’re in a much better position to figure out what kind of investment will actually help you get there.
That might look like a retreat followed by a few half-day working sessions, or quarterly offsites with tighter goals instead of one big annual event.The structure is flexible. The follow-through isn’t.
If you’re thinking through what might help your team or organization right now, let’s think through it together. Reach out to schedule a Discovery call. And if you want to stay connected to practical thinking on culture and what actually drives change in organizations like yours, my Culture Threads Newsletter covers this regularly.
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