S3 Ep8: Coming Back on Monday From a Retreat That Actually Works

A retreat can feel productive while it is happening. People talk more honestly. The tension lowers. The team gets a little space from the pressure of the regular schedule. But if leaders have not named the real problem before the agenda is built, the team usually comes back to the same habits on Monday.

Jen closes this season by walking through what actually makes a retreat useful: clear purpose, behavioral goals, timing that interrupts old patterns, and enough structure for conflict to become part of the work instead of a complaint session. Fun can help people breathe. It cannot carry the conversations leaders have been avoiding.

This episode also gets into psychological safety, accountability, and the guardrails teams need if they are going to be honest with each other without letting harm or avoidance run the room. The work does not end when the retreat ends. It shows up in decision-making, meeting habits, follow-through, and whether leaders keep the hard things visible after everyone is back at work.

If you are planning a retreat or team session between July and September and want help designing it with more purpose, visit jenfrytalks.com.

Transcript

Season Focus: Retreats And Teams

Dr. Jen Fry 0:00

Hi, welcome back to Five with Friday. 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

Why Most Retreats Fail Early

Dr. Jen Fry 0:22

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, I am Dr. Jen Fry and welcome to the end of the season on retreats. So we're going to do a little recap to help you out. So the first thing that we want to make sure you understand is that many retreats fail before they even start. They are more worried worried than kind of the fun stuff than asking the actual question, what problem are we solving? I need

Fun vs Alignment

Dr. Jen Fry 1:05

you to have behavioral goals, define success in behavior, and really sit down with the what problem are we solving. The next thing is just because y'all have some fun together, go with massages, golfing, I don't know, paintball, it doesn't mean that your team is going to be in alignment. That fun just temporarily lowers the tension, but it doesn't stop and make people think about the tension and work through it. So have some fun stuff on the retreat, but don't have it be too much fun stuff where people aren't able to have the honest conversations that they need.

Timing Retreats As Interruption Points

Dr. Jen Fry 1:45

Next, we talked about what is the real purpose of the retreat and why do you have it when you have it? Having it before the season, before things get crazy. Whenever you have it early on, it's meant to be an interruption point. It's meant to reset expectations, decision-making norms, get people in alignment of this is how we work together. Really understand the blind spots and clarity. It's about understanding the blind spots and how we interact with people, with each other, with customers, whatever it is.

Conflict As Core Work

Dr. Jen Fry 2:23

Then conflict is work. Retreats should have an element of talking about conflict. Talking about the conversations they need to have, how do we reconcile, how do we talk through things, how do we treat each other when things get hard. Those are things we need to be talking about. We can't just use silence. We have to make sure that we have these conversations that are also facilitated, so it's not just a big complain fest and everyone complains, but no one is solving anything.

Safety, Accountability, And Guardrails

Dr. Jen Fry 2:58

From that point, we just kind of have this conversation about psychological safety versus accountability and understanding how important it is to have accountability so that people just can't say whatever they want to say or emote the way that they want it to emote without any guardrails. Guardrails are really important to have a safe place. So it can't just be where the bosses are saying, This is safe, you can trust me. That's not how it works. You have to have guardrails so that people can understand that folks are gonna be held accountable if they say or do something problematic.

Aftercare: Monday Follow-Through

Dr. Jen Fry 3:36

Then we kind of closed out with really understanding why retreats fail. Everyone had this great retreat. They they're suntanned, sunburned, look like a lobster, whatever it is. And now we're coming back on Monday. Understanding that we have to pay attention to what we expected, what we talked about, the things we pushed on. We have to think about those type of things. Thinking about what behaviors do we want changed and how are we showing those behaviors. It can't be that we just go silent. It is that we need to fully understand what things that we talked about, those really hard things, those need to be front and center and consistently worked on after the retreat. It doesn't matter how everyone was amazing during the retreat if those things aren't being discussed, managed, and implemented after the retreat. It's a massive leadership fail if they don't really put their hand on the polls and make sure that they're fixing the things that need to be fixed and knowing that's gonna be gradual, can't change overnight, but there has to be the steps to get

Work With Dr. Jen Fry

Dr. Jen Fry 4:52

to that. And friends, I want to help you out with that. So if you're planning a retreat or a team session between July and September and want to actually change your culture, email me at bookings at genfrytalks.com or go to my website at genfry talks.com and fill out the form. We want to help you get better with your culture. So a treat is a true reset. 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.