Offsites and retreats aren’t just a nice-to-have—they’re a strategic lever. In this episode of Stepping Into Your Leadership, Christine Courtney is joined by Greg Shammy to explore when offsites are worth the investment, how to design one that drives results, and how they can deepen team connection, alignment, and trust.
“If you can muster the energy, time, and money, you can make transformational changes in your business that could never happen without an offsite.” — Christine Courtney
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Christine and her team have facilitated dozens of transformational offsites. Reach out to us here to start planning yours.
Christine: [00:00:00] Hello everybody. I'm Christine Courtney, your host, and I'm so happy to be in the studio today with my partner in crime. Greg Shammy is here with us today. Hey, Greg. Hi everybody. How's it going? Today we are gonna tackle the topic of offsites, or some of you may talk about them as retreats or. Company getaways, whatever you call it.
We'll probably refer to it mostly as either an offsite or a retreat and whether is it worth it or is it a waste of time. That's what we're gonna jump into today. I think Greg and I have similar views on this, but we'll try to also point out the other part of this view. All right, Greg, so what's your thoughts?
Greg: Well, when you said is it a waste of time, I also said, is it a waste of time and money?
Christine: Mm.
Greg: Because it's, it can be very costly.
Christine: Yeah.
Greg: And that usually becomes one of the. Number one deterrence is, you know, why are we gonna spend all this money to go somewhere else? Mm-hmm. So I always appreciate that because, you know, we run a business and [00:01:00] we're thinking the same thing.
So like, why do we do offsites for ourselves? Yeah. I mean, even just starting with that, well, a couple of things come to mind. One is getting into a different environment is. Huge. Right? Just even in terms of distractions, being able to go somewhere other than you are at every day together is a great way to begin.
And that makes me think of that quote, you know, coming together as a beginning, keeping together is progress. Working together is success. But the coming together. Is very important. It's the beginning and you need to come together with your teammates and so coming together in a different place, those are the two things that come to mind that are super important when thinking about why invest.
Offsite.
Christine: Yeah. Because you know, I talk to business owners and managers all the time, and they're like, oh, the thought of one, either the cost, because sometimes it's very expensive. You're oftentimes flying employees somewhere, right? So it better be worth it what you're doing. So you're, you have cost of airfare and [00:02:00] transportation, or you are paying for them to, you know, get there.
You're paying for rooms, oftentimes. You're paying for catering, you're paying for space, you're paying for facilitators. It adds up, right? So when you have to, if you're the manager or the leader, or. The owner and you're having to justify that. You need to be able to show an ROI, right? What's your return on investment on what potentially could be a huge investment depending on what your offsite is.
So that's one of the problems. The other problem is that sometimes you get flack from your employees who don't wanna leave their homes, their families, their spouses, their kids, you know, any of that could put a lot of pressure too. And sometimes people's anxiety comes up if you, especially if you have the kind of budget where you have to share rooms or, you know, people are like, I don't like.
Working that late, or I don't like hanging out, I don't like drinking. Whatever it is that's going on. There's so many thoughts and feelings that you have to manage that. Sometimes people just say, oh, forget it. You know? We'll just keep going on as is. So I think, are there any other things that get in the way, any other roadblocks that.
Make it sometimes not [00:03:00] worth it. Like let's just put voice to those things and then put voice to the other side of why it might be important to do this work.
Greg: Yeah, it's just, it takes a lot more energy all around to make these things happen again, if they're gonna be effective, they have to be organized really well.
Uh, you want everybody to be having a great experience, not just. Hotel and food and environment, but also the actual content, right? So it takes a lot of effort to, to really dig into these things, so that can become a, an obstacle as well.
Christine: Yeah, and I think those deterrents oftentimes stop us. And if they're too big for you, it might not be the right time, because you're right, it does take a tremendous amount of energy, and if you're the person spearheading it, you have to have more energy than anybody to make it, to overcome all those barriers.
That being said. Greg and I both really strongly believe in the power of offsites or retreats for your company. And I'll tell you why. Because if you can muster the energy, you can muster some time and some money you [00:04:00] can make for. Transformational changes in your business that in some cases could never happen without this offsite or retreat.
So let's dig into that because if you have an inkling that this could be right for you, you're probably, I would tell you that gut feeling is right and not to let all those barriers get in your way. Push through, because my gosh, have I seen change in my own company? In myself when I've done things just alone for myself when I've done it for my company.
Incredible change. And when we facilitated for other companies, so this could be from a very small experience to very large, it could be a half day at Central Park to, you know, flying your folks to Colorado. Like it, whatever it is. There is a spectrum of possibility, and I would say to you that don't let your.
Like worries about money or time get in the way if you really wanna do it. And let's talk about some of the benefits. So Greg, what do you see? What's one benefit that you have seen?
Greg: There's so many benefits I've seen, and I'm [00:05:00] thinking about actually the ones we've done for people, right? Like we were saying, we, we, we do our own offsites, uh, for our internal teams, but doing it for, for clients.
Something that sticks out to me is that once you've organized this. In an effective way, and it starts, you have your people all together there with no distractions, and so you're gonna get a hundred percent, hopefully once they buy in that, Hey, hell, this is well organized. This is nicely done. Oh, this is interesting content.
Oh, this is really pertinent and relevant to my job and to us sharing. Information with each other and building a cohesive team. So like, you know, most of the time I'm being pulled, left, right, and center, and I'm just doing the job as best I can and I'm missing the connectivity. And so the biggest benefit that comes to mind is the connectivity that happens between me and my other players that run the company and being able to get sparked.
Buy that sharing of information, sharing [00:06:00] of ideas, strategy, all that stuff that's gonna be coming out of these sessions that we dig into a hundred percent together, where we never have that opportunity 'cause we're working.
Christine: Yeah, I love that. I love it. So really we're talking about connectivity one, two.
Limiting distractions from our lives, right? So that we can focus all together. Focus could be incredibly powerful. And I think that idea you alluded to, but just to underline it for everybody, is taking us out of our natural environment, taking us out. Whether it's that you work in the same cubicles all the time, taking us out of that environment, or whether you're remote and you're finally coming together, or whether you're hybrid and you finally get to.
Interact with different people in person. All of those things are really critical to taking us out of our every day and putting us in a new space because it opens up our brain to actually be more innovative. Think of new ideas, connect in, like you said, in different ways. Um, I think another definite benefit besides those things are also this idea of creating experience.[00:07:00]
With your team members. You know, one of the things they say is if you, the research shows, you know, if you buy somebody a gift that lasts for it has a very short lifespan in terms of what it gives you, right? The joy it gives you, the feeling it gives you. However, if you have an experience or you spend money on an experience.
What that shows is that actually grows over time. And so you could, we have memories, for instance, just us, we have memories of our people at retreats for, you know, 20 years now, that we bring up a, a line or a moment and everybody laughs or everybody immediately gels together and that you cannot pay enough money in the world for that feeling.
And studies are showing that the younger generations want and crave experience and experience with others more than older generations. So if you're the type that's like, I don't need that, well think about your younger folks, because they are, they travel more, they go out to dinner more, and they also like to, uh, retreat together, create [00:08:00] experiences together, be in nature together, be in, you know, challenges together.
All of those things that you can create. At an offsite that can actually last you the whole year, especially if you don't get that kind of connection all year long. Did you have a thought, Greg?
Greg: Well, yeah. I just, I love this whole creating experiences 'cause that's what we do. And in reflecting back on our, our own personal, uh, offsites, I mean, the memories are just.
Gargantuan and, uh, incredible and that most of them like are from challenges that we had where we had to overcome a problem. Uh, we were put into like team building challenges and they were super fun. We all had to figure out what our strengths were, what our areas. You know, that we could bring to the team in order to, to overcome the task.
And then we had to do it. And in that we created these like emotionally exciting experiences that last forever. And so what does that do for me in the workplace? It does a ton. Mm-hmm. Because what happens to me when I'm back. In the river doing the work. And I [00:09:00] look over and I've had this really super fun experience where I've overcome some stuff together with another teammate and we have to work now with this client and really make sure that we're doing the same concept but in the workplace.
And it's a phenomenal bond that can never, it can't be erased.
Christine: Yeah. I've seen team members who do not get along, like who have lots of conflict come together at a retreat with. Maybe it's a moment, uh, singing a song around a, a fire, a bonfire, or it's, you know, doing karaoke or it's come, it's doing a challenge, a ropes course or something where all of a sudden those two people are bonded like crazy.
And so it doesn't take away all the conflict in the workplace, but it certainly lightens it up and gives them a new vocabulary. For how they can communicate or how they can be together in a different way.
Greg: You're just like barking a, a memory of mine with a team on an offsite, uh, this was a client I was facilitating and two of the members didn't speak and I remember the CEO had come up to me and was like, listen, these, these folks are, have some [00:10:00] serious conflict and so it's gonna be awkward.
I just want you to be aware of it. And that helped me a lot as a facilitator. 'cause then I was aware of it and I could slowly scaffold or build in the importance of getting their voices into the space. Slowly, the different perspectives, validating the perspectives that were coming into the space, having them do activities, but knowing how to group them and then.
Getting them to eventually connect and and bond. And it happened. And it was the most incredible thing that took place where these two people didn't really communicate at all, did their jobs separately from each other. And there was tremendous conflict. And by the end of this offsite, there was a bond that had been created.
And that to me was a huge success.
Christine: Yeah.
Greg: Yeah. So that, that conflict piece is huge. Like if you're having toxicity and conflict in the workplace, hello everybody. Another benefit can come from these getaways together is to resolve some of that.
Christine: Yeah. And you see it right away. And what's good is that you're having fun or you're doing something that's different.
And so it takes a little bit of the stress [00:11:00] off of the work itself and actually makes the work product go further because you're pushed in a different way. Your, your defenses go down a little bit. You see something differently. There's a little bit of breath and space around it. Before we get into tips on how to do this, Greg, yourself and, and it could be on a budget or it could, you know, be that you have a large amount of money to use.
But before we go into that, I also wanna say that it's really important to do these. Kinds of offsites, not just with your company, do them with your spouse, do them with your best friends. You know, you can really change the quality of your relationships just by doing it. Do it with your kids and, and call it this, you know, we're gonna go, instead of it just a vacation, we're gonna do a family retreat for the weekend.
We're gonna talk about our core values as a family. Or if it's, you know, in my case I go sometimes with my girlfriends and we always, you know, have some sort of idea of. Growth and expansion and fun that we're gonna put into it. Alright, so let's talk about some tips on how to do an offsite, if you're thinking about doing it, what's one tip that you have, Greg?
Greg: Well, [00:12:00] I think I, you know, what becomes most important is when I've decided I'm gonna do an offsite is. Figuring out what you wanna get out of this. What is your super objective, as I like to call it for this? What are specifically the outcomes you wanna have by the time this is over? Whether it's a half day, a full day, a three day experience, right?
And so getting clear on what you want the results to be, I think is super important. And that gives you a really a big objective to go for that helps align everything else.
Christine: Yes, I'll add on that. I, um, in doing our own retreats, I'm always coming up with a theme of what's important for the whole year. And a lot of times, I'd say all the times, this does not come from me.
So I go to the folks that are kind of key people at identifying these within my organization, and I ask them, what do you think the theme should be of this retreat, which will then impact the entire year? So for instance, this particular year, somebody in our organization. Said, I really wanna focus on this idea [00:13:00] of buoying each other, of being buoyed to each other, of being connected when things are tough, of being kind of buoys for each other.
And so I, that stuck in my head and I just wrote down that thought. And then I thought, okay, and I talked to a few other people and while they didn't use the term buoy, they used, did use the term of being, trying to stay connected to each other when times are tough. And so I went back later when I looked at it.
And I thought, okay, what's this idea of buoy? And I went into like kind of a deep research of that word and so forth, and then started to structure activities, especially in the beginning, and that they would do at the end that were related to that theme. So then the challenges that we had, I. For instance, we created buoys, uh, real buoys that teams created that had to float out of objects.
You know, they had cardboard and they had duct tape, and they had floaties, and they had rope, and they had markers, and they had to create something. They had to create a, a floating buoy that they could put out into the water That. Could stay up and flow, but also reflect themselves and what they [00:14:00] bring to the group.
And so that was written on it with markers and stuff. And so that started off our retreat, getting them thinking about that. Like who am I? What do I give to people? How do I buoy other people? How do we stay buoyed together? And then hopefully throughout the retreat you have some activities that while they will go off and touch other things, touch upon that theme.
And then when the other person that I was facilitating with at the end of the couple of days. She went back and did an activity that referenced that Buoying idea and kind of put a bow in it so that this year when we come back to our meetings or we talk about things, everybody's on board with that image or that visual of being buoyed by each other.
So that's just one idea of a theme we have. They're different every year. Sometimes they've been around fire, sometimes they've been around the rocks that we carry. You know, there's all sorts of different themes depending on what's going on with the organization, and I never trust myself to know. So I always ask some people who really are attuned to others and what's going on with everybody to kind of sit with their ideas for a little while before coming up with the themes.
So I think that's
Greg: a best [00:15:00] practice, Christine, for sure. And a great example to have. That kind of thought prior put into this and, and getting a group of people together in your, on your team who are interested in gathering this kind of information and then coming up with these ideas based on what they gather from the team members.
I think it's fantastic and it, it really does set you up for success. Uh, and I love the idea of like, why are we doing this? Why are we making this investment right now? And how is it gonna benefit us for the next chapter? Yeah. Right. Moving forward. I think that's absolutely key and very helpful to do.
Christine: Even if we are doing this, not for our own company, but for other companies. We go through a process of helping them, like Greg said, what are the outcomes you want so that you leave this retreat? What feeling do you want everybody to have? And then we work backwards from there. And also, what's do you perceive as things that could be the theme for the year?
What would you want? Sometimes those are around alignment. If everybody was really focused in the same way, like a special forces troop, we've done things. Round that kind of special forces idea or a a [00:16:00] sports team, how do we get people on board with those types of feelings? It could be anything depending on where you are, but if you start with the end in mind, Greg, you're a hundred percent right, you're gonna have more chance of reaching that goal.
What else? What's another tip that we have? I have one if you don't, yeah, go ahead and let's, uh, build on it. Okay. Two, I would say find other people to help you. So don't think you're gonna do this alone. It's a lot of work. Find other people to help you, whether that's if you have a budget and you can hire somebody to, at the bare minimum, facilitate because facilitator is much.
Harder role to fill than the people who can coordinate all the activities. While coordinating might be sound difficult to you, I bet you have somebody in your office that can do that. But facilitating allows you as a leader to also step back and participate rather than having to do dual roles as facilitator and participant.
So it, it's really nice and such a luxury when I've been able to step back and let somebody else facilitate to really see things. Clearer. Watch how my team, uh, reacts, how they participate, look for things that I can't always see when I'm facilitating. So if you have [00:17:00] any sort of budget, that to me, that piece of it is key.
But also if you don't, there are people on your team that can help you in so many ways and to give people pieces of things to take over, whether it's you're in charge of this lunch or you're in charge of this hike, or you're in charge of coming up with what activity we can do at night. People love to do stuff, they wanna be involved, and it takes a lot of pressure off of you.
Greg: I think that's a, a great point and being able to delegate the pieces out right and bring in different energies to do different things. Uh, a lot of times we do the whole thing, but sometimes we'll go in and do a piece too. If it's like they want a strategic vision session, you know, uh, 1, 3, 5 year vision type of thing with like working on res, solidifying their values or what have you.
We can go in and do that in a half day. It's nice to have other people come in and do something really effectively. 'cause then it also propels your. Other folks to be when they're standing up to do something, to be inspired by that and learn from that and be able to bring something exciting, uh, themselves.
Christine: Yeah. [00:18:00] Tatiana, our producer wants to say something. Yeah,
Tatiana: I, I have a tip too. My Yes. Anne to Greg's tip of having someone outside do it is also. Making sure that you're processing activities. I remember one retreat where we had to build a bridge that a car would drive over and we failed miserably. And so the outside facilitator was determined that we made this bridge.
So then their staff started to build the bridge for us.
Christine: That's right.
Tatiana: I was appalled because the activity we failed and the learning that could have happened if we would've discussed, and we did because of course Greg was not gonna let it go. But we had to process that we failed because we failed sometimes and that's okay.
And that was such a missed opportunity. So I think, yes, have an outside person do something, of course. 'cause I love that. But also making sure. That the activities are processed. Yes. And that you're questioning because that is where the learning is gonna happen. And that's where the connection back to your theme is so important [00:19:00] because like it's, it was such a missed opportunity for that organization to help us go through talking about failure.
And I, and I always remember that as a big fail for them, I would never use them again for that one reason.
Greg: And just to clarify, for. Folks listening when Tatiana says process, you know, that's our language for really debriefing post any kind of experience or activity that you do. It's really like, okay, well what happened, uh, for you, uh, what had happened for us as the group?
What, what lessons came out of it? What did we learn and what are we gonna do? Differently moving forward. I mean that simple, just asking the your team members those questions and that's gonna lead you into them having some realizations that are gonna be super helpful and connecting it back to their work.
Christine: Yeah, and that is the difference between having professional facilitators and having people who just maybe work at the hotel who run an activity. If they're running aero tag, they know how to set up aero tag to keep you guys safe. But they don't know how to process the activity with you. So don't expect that [00:20:00] those folks are knowing how to do that, because that's, that is a definite skill that you need a facilitator to do.
And Tatiana, thank you for reminding me of that moment. That was incredible. Because you could tell that their goal was for us to succeed, even if it meant them themselves doing it, not us, right? And so we had to process that. Kind of on our own separately. That's a good reminder. Alright, another tip is to think about, uh, a combination of activities.
So no matter if you have, if you're doing this in your backyard because you have no money, or you can get the most, you know, high priced hotel in Switzerland, you wanna have a combination of activities to appeal to everybody. So you wanna have a combination of some sort of nature and outdoors. And I gotta tell you that.
Probably the number one complaint we get from people who do, who go to offsites is that they go to these beautiful places and then stay inside a conference room all day. That is a hundred percent the number one problem. And the problem, I understand it from the the ownership point of view is you've gotten all these minds together.
You're [00:21:00] paying all this money and you wanna have these sessions, these thinking sessions, these planning sessions. And it's difficult to do that outside, right? But you really wanna have as much. Experience with nature or wherever you are outside that is different than what they're used to. They will be very frustrated if it's a beautiful day and they're inside looking out at windows and the night comes and they're like, oh my God, why were we even here?
We could have been in our offices or on at our homes. So think about how to make sure that you're incorporating nature outdoors, that you have some sort of combination of fun, uh, that you have some sort of challenges, like physical challenges like Greg was talking about, but also maybe like. Puzzles or mind challenges or also hands-on building things like some people are builders and like to, you know, do kind of art projects within their challenges.
And then some people are real sporty and physical and wanna have some sort of physical challenge. So you wanna have a little bit of both so that everybody's a little outside of their comfort zone, but not outside their comfort zone the whole time. Right? You wanna have [00:22:00] something where they're also in teams, so people who like to do that stuff can excel and other people can sit back.
And so you have this idea of I'm leading now I'm stepping back. And everybody has a chance to feel good, and then also people have a chance to like assess. Uh, themselves and you know where they are and where other people are.
Greg: I think it's so good, Christine, that variation is key and I like to get those team building stuff, activities going early on as I build the group, and then from there, dig into strategic stuff.
Because once I've had that experience, then I can like, oh, I'm not only physically and mentally perked up and ready, but now I'm ready to dig into, okay, let's look at the business and let's strategically, you know, come up with some plans and action plans on how we wanna move this forward together based on where we're at, what's happened in the past, and how we wanna move forward better.
So I, I, uh, I think it's, combining activities is huge.
Christine: Yeah. Perfect. And it's. The way that he just structured it, really important. So first, when you get there, you break the ice with [00:23:00] some immediate, fun, low stakes team building. You don't jump into a huge ropes course right away. You start off with some very light, fun, get to know you, you know, everyone's nervous, so you're a little more comfortable.
Lighthearted fun and do that outside. If you have a beautiful day, do those activities outside a hundred percent so that people are outside right away. I just was with this past few days with a group of CEOs and that's what we did. It was beautiful. Few days we did outside. I had them do activities to get to know each other, working in teams, fast paced music, on dance, whatever outside in nature.
And then they went after they were doing that and got to have some interaction with the whole group. They went on a, what we call a wisdom walk, where they walked around the lake that was there. So not a difficult walk, but a, you know, a hike but flat mostly. So everybody could do it. But then along the way, they had these huge ducks that they had to find, uh, rubber ducks, and they were colorful, so you could spot them along the way.
And then underneath it said a question or prompt for them to talk [00:24:00] about. So it could be like, what's the biggest risk you've taken in your business so far? And then you put that duck down and you walk and talk and so forth along the lake till you find the next duck that leads you to what keeps you up at night.
Right? So these were questions that were for a bunch of different CEOs, but for your company, you could see how that wisdom walk could be related, right? Then, that first day you've left, really, you've had some good one-on-one time, uh, you've had some good group time, and then you're gonna have a great. Meal and some fun at night, and then the next day, Greg's right, dig into some content inside focused, you know, whether it's your vision, mission, values, whether it's your goals for the year, whether it's how to get more aligned, whether it's learning a new skill, I.
Whether it's learning, working genius, for example, or, uh, certain kinds of leadership styles, whatever it is that your group needs. And then you can spend the night, you know, at outside again that night and, uh, doing something outside. But that indoor time is important because you're gonna lose them if you're outside working on alignment and strategic vision.
Greg: Oh, you just [00:25:00] made me think of another important piece before we bring this to an end too, is, is the ending itself and how important the, the final activities are of an offsite. Because it gives, again, the importance to the, their voices of the participants and the experiences of the participants. And so doing a really strong closing that allows you to reflect back on why we did this, what came out of it, what got sparked for you, what, what's sticking with you and what are you gonna put into action?
Because yeah. Which is absolutely so important is, is huge. And, and then some, obviously, some appreciation is something we always like to build into because then you end up leaving with, uh, an opportunity to, to give some, some props to your fellow teammates based on the ex creative experiences you've had together.
Christine: Yeah. And feeling that back. Right. That's a great feeling to leave with. Yeah. So those are two great things. Action steps, your takeaways, and then some sort of appreciation, gratitude for this time together and for each other. I also just wanna say that just as important as the ending, which it is. Because it's a catapult, right?
It's a catapult to spring from is the [00:26:00] beginning. How do you make people feel cared for? You know, I have some folks on my staff who are great at this, and in the past they've thought about it. Do we have a bag made for them? Do we have some swag that they don't know about that we leave in their room? Do they get something that makes something, you know, with snacks or things that are carefully curated for them?
Can make somebody feel really appreciated, and I always start by thanking them for giving up this time with their family and friends and pets and so forth to make this happen. That's really key to like letting everybody let go of any sort of bitterness or feelings of like, why am I here? I've got so much stress at home, or I'm, I gotta find a dog sitter, or whatever it is.
Greg: You always do that. It does. It totally is like, oh, thank you for acknowledging what I've had to do to come here. So I always really appreciate it and it, it does allow me to, to sink into what's about to come. Yeah. The other thing I just thought of, Christine, is, so the beginning, the ending there, obviously super important as the ending happens, what's.
The next connection to what just happened. So if you do come out of it with someone who's [00:27:00] put together, you know, some company goals or whatever content you've created in the offsite together, right? That's gonna propel you forward. What are the next steps? So the debrief that happens post the offsite. How do you keep that energy going post the offsite?
So most people, it just drops. And so having intentional connectivity to that I think is huge.
Christine: Huge. That's a great last thing to leave everybody with. Um, we hope you try it. Even if you have no money, don't let that stop you, even if you have no time. Like I've said, I've done them in the park where everybody's met at the park with their.
Metro card or whatever in hand, they bring their own lunch. If you can't afford it, but just get out of your norm at least once a year, people will remember it. It creates experience if you have a ton of money to do something really cool. A friend of my CEO took all his staff to Red Rocks this year in Colorado.
What an experience they had there, right? You can do anything that you're gonna put your mind to and your staff will remember it. So. Jump into it. If you need help, reach out [00:28:00] to us. We're happy to give you ideas or help. Our website also has lots of ideas and and resources for you. So thanks you guys for listening, and we'll see you next week.
Thanks, Christine. Appreciate it. Thanks, Greg.