I still remember the first interviews I did with Darcy ahead of a team retreat. We had 25 minutes with each team member, eight interviews in all. The team retreat would take place in the next month, and these interviews would determine the agenda we created for the retreat.
Everyone on the team got the same questions. Ahead of the first interview, I was skeptical about how much information we would actually get. Conversations of 25 minutes didn’t feel like nearly enough time. Additionally, we were strangers to these people. How much were they really going to tell us?
I was shocked at how wrong I was. While each conversation was different, everyone was eager to talk about their team and what was working and what was not. The emotions ranged from optimism to cynicism, from frustration to eagerness.
And that’s where something started to click for me.
People are more than willing to talk about their team. They care. They have opinions. They want things to be better. But what they say in those conversations also reveals something else.
Even when people are open, there’s often a layer of skepticism sitting right underneath the surface.
And while every team I have interviewed has varied in how they answer questions about their specific situation, I have gotten used to hearing very similar responses when I ask, “What would make this retreat valuable to you?”
Sometimes it’s easier for people to say what would make it not valuable:
- Don’t force me to talk.
- I don’t want it to turn into a blame fest.
- No trust falls (I mean, seriously. Are people still doing this? I’m amazed at how often this comes up!)
When people do answer the question directly, the most common response is that they want something to actually change. But right alongside that is a quiet question of whether that’s even possible. Even if people go into a retreat hoping for the best, there is often a stronger desire to just survive the day.
And for people who have been through “bad” retreats before, or who have only seen them play out on TV (remember Beach Day on The Office?), it makes sense. A lot of the hesitation around team retreats is understandable.
Four Reasons People Are Understandably Nervous About Team Retreats
There are a lot of reasons people get nervous when they hear the words team retreat. Here are the ones we see most often:
- The fear of awkward, forced activities
For many people, the first thing that comes to mind when they hear “team retreat” isn’t strategy or alignment. It’s activities. And not just any activities, but the kind that feel somewhere between summer camp and mild social torture.
People start wondering what they’re going to be asked to do, and more importantly, whether they’re going to have a choice in the matter. There’s a big difference between engaging in a meaningful discussion and being told to participate in something that feels completely disconnected from the actual work. You can almost see people bracing themselves for it.
- Please don’t make me hold hands with my coworkers.
- I’m not climbing anything, jumping off anything, or catching anyone.
- If there’s a hula hoop involved, I’m out.
Even if none of that is actually planned, the possibility is enough to make people uneasy. That association has been built over time, and it sticks.
- The worry of being put on the spot
Ok. So if we aren’t going to do crazy activities, then the only other thing we can do is talk. And for some, that’s even scarier than the hula hoop.
People don’t always know what’s going to come up in a retreat, and that uncertainty can feel risky. What are we going to be forced to talk about? Are people going to be expected to give feedback to other people in the moment? Do I need to be ready to defend myself? And if we are going to talk about what’s really going on with the team, where is the line between a productive conversation and something that starts to feel a little too much like group therapy?
It’s not that people don’t want honest conversations. It’s that they don’t want to be caught off guard or pulled into something that feels unhelpful, overly personal, or disconnected from the actual work of the team.
- The feeling that “if we need this, something must be wrong”
This one doesn’t always get said out loud, but it shows up a lot. When a team retreat gets scheduled, especially with an outside facilitator, it can quietly trigger the question: Wait… are we in trouble? Am I the problem?
Even on strong teams, there can be a sense that retreats are something you do when things aren’t going well. So instead of seeing it as an opportunity, some people experience it more like being sent to the principal’s office.
- The concern that it’s not worth the time
And then there’s the very practical question: Is this actually going to be worth it?
Teams are busy. So when you ask people to step away from their work for half a day or a full day, they’re doing the math.
If this turns into something vague, repetitive, or disconnected from what we actually need to get done, that’s a tough trade.
What’s not getting done while we’re sitting here?
Are we going to leave with anything concrete?
Is anything actually going to be different next week?
This is where past experiences matter a lot. If someone has been to a retreat that felt like a long conversation with no follow-through, it’s hard not to carry that expectation forward.
What a Good Team Retreat Actually Looks Like
When a team retreat is done well, it doesn’t feel like any of the things people are bracing themselves for.
A good retreat should feel thoughtful and specific to the team. There should be a clear sense that the conversations are there for a reason and that what’s being discussed actually connects to how the team works together and what they’re trying to accomplish.
One of the things I’ve learned from those pre-retreat interviews is that people already have a pretty good sense of what’s working and what’s getting in the way. They might not always say it in a meeting, and they might not always know how to bring it up, but it’s there.
A good retreat creates the space for those perspectives to come out in a way that helps the entire team start to understand what’s really going on beneath the surface. And when that happens, something shifts.
It’s not that everything suddenly becomes easy or that every issue gets resolved in a single day. That’s not a realistic goal. But there is usually a moment where the team starts to see itself a little more clearly, and people realize they’re not the only ones experiencing something.
From there, a good team retreat should lead to a few specific next steps the team is committed to trying based on what they uncovered that day.
And maybe most importantly, a good retreat doesn’t end when the day is over. If there aren’t immediate takeaways and actions the team is committed to, everyone just goes back to business as usual.
Not All Team Retreats Are the Same
So yes, when people hear the words team retreat and feel a little hesitant, a little skeptical, or even a little resistant… it makes sense. A lot of that reaction has been earned.
But not all retreats are the same, and not every team needs the same kind of retreat.
Some teams need space to get aligned. Some need to work through tension that’s been sitting there for a while. Some are growing and realizing that what used to work isn’t working the same way anymore. And some are doing well, but know they could be even better if they slowed down long enough to be intentional about how they work together.
And let’s be honest. Maybe your team does need a beach day (minus the firewalking).
The point is, the hesitation isn’t the problem. The question is whether the retreat is designed in a way that actually meets the team where they are and leads to something different on the other side.
Because when that happens, it stops feeling like something to get through and starts feeling like something worth the time.
Thinking about how to choose the best experience for your team’s current needs?
