S3 Ep1: Why Most Retreats Fail Before They Start

Everybody usually knows why the retreat is happening before the retreat ever starts. The problem is that teams often build the agenda around relief instead of clarity. So people leave with photos, a few good moments, and the same tension waiting for them the next week.

This conversation gets underneath that pattern. Jen talks about why vague goals like “we need to communicate better” keep teams stuck, and why a retreat only becomes useful when the actual problem is named clearly enough to work on. Not the polished version. The real one.

She also gets into leadership accountability, because retreat failure is rarely just about staff buy-in. It shows up when the people with the most power avoid looking at the behaviors that are shaping the room in the first place. If leaders are unwilling to name what they need to change, the retreat turns into a break from the problem instead of a turning point.

The question is simple: what needs to look different by Monday? If you’re planning a retreat, leading a team, or trying to figure out why your offsites never quite land, this episode gets specific about what has to be named before anybody walks in.

Transcript

Season Focus: Retreats And Teams

Dr. Jen Fry 0:00

Hi, welcome back to Five with Fry. I'm Dr. Jen Fry. This season is all about retreats and team dynamics. Because most retreats don't fail during the retreat. They fail long before anyone walks into the room. Organizations spend thousands hoping for alignment, better communication, stronger culture. But too often teams leave and return to the same problems on Monday. This season is about changing that. We'll talk about what actually makes a retreat worth the investment, how conflict and communication shape team dynamics, and how retreats can become real turning points instead of temporary resets. If you're planning a retreat, leading a team, or wondering why your culture feels stuck, this season is for you. Let's get into it. Hey friends, welcome to episode one of this new season, and we're going to talk about why most retreats fail before they even start. Retreat season is a really big reset for organizations, staff, department, whatever it is, kind of this team building. We need to reset before it gets really busy. But the thing I will caution is that many times retreat failure, it begins literally in the planning stages, not in the facilitation. It's not in the activities that you do. It's not in going golfing or any of that stuff. It's not. What it is is that it's kind of asking what are these defined specific outcomes that we want to have that we want people to leave with that Monday morning? We can name what specific changes we want to see. And that's where we just tend to see a failure. And it's never situated with this idea of what problem are we actually solving? We need to have this retreat, we need to have this reset, we need to have fun. But what actual problem are we wanting to solve and really willing to name the problem that needs to be solved? Not in a very generic, overarching theme of the staff needs to communicate better. That is a generic thing that can have so many different spokes to figure out how to fix it. But it's really saying, what specific things do we need to solve that can create better relationships, better outcomes, and just a better enjoyment of the job. Because in the reality of it, if those things are met, you're gonna see innovation, you're gonna see growth, you're gonna see scaling, you're going to see the things that you want to see if you're willing to ask the hard truths and then find ways to start working on said hard truth. I'm not saying that you can't go have golfing or you can't have these fun activities. You can absolutely have those, but they can't be the central thing that you plan everything around. Because when that occurs, you're not getting down to the nuts and bolts, the hard things that actually need to be solved to help the reset and moving into this new year or this new season or whatever it is be actually worth something. And that's what your ultimate goal is is that we are going to this retreat, we're spending thousands of dollars, hundreds of thousands of dollars for our employees. We need to have actual tangible things that show from this. And sometimes that means that with that reset, we have to pull scabs off. We have to start asking the question of why are we having this problem? What is causing this problem? Where at the top is it causing this problem that is ultimately trickling down and hurting everyone else? What about leadership do we need to start fixing and start acknowledging that we need to fix to then allow other employees and supervisors and directors to start fixing things? Because there's nothing worse than being at a retreat, knowing the problems that need to be fixed, and everyone else is glossing over it with a, oh my god, we get to go to the spa, oh my gosh, we get to go golfing. And everyone knows what the big issues are, but they're not really being solved because people don't want to actually go down to the foundation and dive into why we're having these problems, because that can mean behavioral changes, not just from the employees, but more importantly from the ones who are leading that. And so, you know, the takeaway I want you to have from this episode is that we need to define success and those behavior changes, both at the top, at the middle, and at the lower employees. It's not about the pictures and having fun. It's about what are we define for success in terms of behavior? Because that's going to change the outcomes. And that's what you want from this retreat is change. If this episode resonated with you, take a second to follow, rate, and share it wherever you listen. And if this conversation hits closer to home and your work, I also do keynotes, workshops, and facilitation. My goal is to help one million people have a better relationship with conflict, and it starts with you. Well, that's this episode of Five with Fry. Y'all take what you heard, sit with it, and use it. Remember, growth lives on the other side of that conversation. Don't waste the conflict, and thanks for listening.