As you learned if you listened to this Wednesday’s episode or read this week’s blog post by SJ, our team spent a week together in Denver for our first in-person retreat since COVID. Check out episode 529 with Jillian and Tony, two members of my team who were there in Denver. They help run our membership community and events and have a ton of experience and insight in community building. They’re also the hosts of SPI’s newest podcast, The Community Experience!
In episode 529, I talked about the importance of meeting your team in person. Our team is fully remote—we’re located all over the United States, and we don’t have an in-person office anywhere. So it’s really important for us to meet in person because there’s just no replacement for real, human connection.
That’s why today I wanted to talk a little more about the retreat. Specifically, I want to talk about the dos and don’ts of running a retreat, in case it’s something you’re thinking of doing for your own remote team.
SPI 530: The Dos and Don’ts of Team Retreats
Speaker 1: Welcome to the Smart Passive Income Podcast, where it’s all about working hard now so you can sit back and reap the benefits later. And now, your host, he’s got a secret collection of microphones, Pat Flynn.
Pat Flynn: It’s Pat here, and as I mentioned in the previous episode, I just got back from Denver. I was there for a retreat. If you haven’t listened to the episode 529 with Jillian and Tony, who are two of the team members here at SPI who help manage SPI Pro, it’s a great episode. Absolutely fantastic episode about community. I highly recommend you listen to it.
But I wanted to talk a little more about the retreat. I’m not going to get into the specifics of decisions that were made and things like that. That I’m going to save for the episode with Matt, my co-CEO and COO, coming up later in this month. But I wanted to talk to you about the dos and don’ts of running a retreat and what to do there, and why we did this in the first place.
And you might remember from the last episode, I talked about the importance of meeting your team in person. I mean, our team is all over the United States, right, so we’re all remote. We don’t work from an office or anything, but it was really important for us to meet in person because we could get that true connection and hugs in. Of course, we all made sure we were tested and we did all the safety protocols to make sure we were all safe together, of course. During this time, you kind of have to do that. But beyond that, it was just really nice to be in person. I think that’s really important to do every once in a while, especially if you’re a remote team, maybe even once a year to have an outing to where you can get business decisions made, but also play together and have some fun and do some entertaining things to bring the team together. Because I did notice a very, very clear heightened form of energy and connection coming back.
I mean, the Monday after coming back from Denver, which was just a couple days ago at the time of this recording, it felt like fire. I mean, even though we were all tired, we were all definitely tired and recovering because flights and all that stuff, and we hiked, and we hiked in 12,000 feet of elevation. I mean, it was a lot. I mean, I remember huffing and puffing. I’m a sea-level boy, so it’s hard for me to breathe up at that two and a half miles in the air. Anyway, it was really good.
But let’s talk about some of the dos and don’ts, right? This is just going to be random. I didn’t have time to write an outline for this, and it doesn’t matter, because this is all fresh off top of the head having come fresh off the plane. So here we go. Do make sure to spend time to eat together. Yes, you might be in a boardroom or somewhere getting some business stuff done, and the lunches that happen during that time, that’s fine. But once a day, have a dinner. For example, we had a dinner every single night with reservations at various restaurants where we ate together as a team, and that was really nice because that was the time where I got to know Jillian and Tony and their families, and other things that they were interested in that we just had never really discovered about each other. That’s where we got to laugh and joke and have fun and do trivia and other fun, random things together. Right? So, that was really neat.
Don’t have people feel left out, and I think it could be very easy. I remember working at a company a long time ago where the entire team went out, but I really felt like I wasn’t a part of the team, right, because nobody ever asked me how I was doing. Nobody ever included me. It’s similar to my story about always getting invited to play basketball, but with my friends back in high school, but because I was too short, they would never pass me the ball. They would never let me shoot, so was I really playing basketball? I mean, I was on the court, but I never felt like I was a part of the team, so always making sure people feel included one way or another.
And you know, there are often more quiet folk who might be a part of your team and you want to make sure they’re having fun and get excited too. And that first night can be really difficult, especially if you’re meeting people for the first time. People are still feeling each other out and learning about who’s who and the kind of energy that everybody has together. But again, I think it’s just really important to put yourself in that situation together as a trusted team so that you can get to know each other even more. And again, it carries over into the business stuff that happens later, truly.
All right, do, do have a structure. Matt did a really good job of creating a structure for our meetings, all right? We met from 9:00 to basically 5:00 two days in a row to get some things made. And it was a very, very clear structure with hour by hour, here’s what we’re doing, who’s up, who’s presenting, and what decisions do we have to make, and all that kind of stuff. He had a slide deck. Actually, everybody who was presenting had a slide deck. Again, you’ll hear more about the exact format and stuff, but it’s this idea of divergence and then convergence, which Matt just geeks out on and he’ll bring to the show a few episodes from now, so look out for that. Make sure you hit subscribe if you haven’t already.
But having a structure is very important. It’s very similar to different mastermind groups that I’ve been in, right? Sort of formal groups where it’s five to 10 people and we meet every week to discuss business, but the ones that have all failed were the ones that had zero structure. It was just like, “Hey guys, let’s get together and chat about business.” And it was just like we just chatted about whatever. There was no structure. People didn’t feel heard. A lot of people spoke too much and it was just kind of a dud. But two of the mastermind groups that I’m in have been around for over a decade or nearly a decade, and they’re both very structured.
And so going into a retreat like this, you definitely want to have a structure. You want to have an agenda. You want to have the entire team know about this agenda. And we had it down to the hour and style, and we started off with some icebreaker type stuff. We started off with some ground rules, and it was really smart of Matt because he let us create the ground rules. It’s very similar to what I remember my kids’ teachers doing in their schools, which was allowing the kids to come up with the rules of the classroom, which means, well, that came from them, so they’re more likely to actually obey those rules, right, which is really cool.
And Matt did that with us to make sure it’s a safe space, that silence means you disagree. I remember that being one of the rules, meaning you want to speak up and if you don’t speak up, that means you don’t agree with something, so we’re going to ask you to see why you disagree. But agreement is really important. Getting alignment versus just agreeing to disagree is really important, and all those kinds of things. You know, we talked about a lot of rules up front to create a safe space for us to actually make progress. And we made so much progress. Again, so much can happen in such a short period of time when you all put yourself in that head space.
But again, have other time to do other things, which takes me to the next don’t, which is, don’t go straight eight hours in a row, right? Even with a lunch break in there, multiple breaks. You need resets in between different groups or different presentations where decisions are made. I mean, it’s a lot of energy. A lot of calories are burned with a thing like this. You definitely want to have a lot of water around, but you need to take some breaks, allow people to walk around. Not everybody’s built the same way. Not everybody works the same way. Not everybody loves those kinds of situations, but again, having a plan going into it, and having some structure, really important, and then having the ability to go, “Okay, guys.”
You kind of have to read the room. If you’re leading that group, you kind of have to read the room a bit, and if something maybe went a little bit too long, if you’re starting to feel a little bit lethargic and you could see it in the room, people are starting to fidget a little bit or getting distracted, like, “Let’s take a break. Let’s reset,” and that’s totally okay to do. Definitely, you want to move things around if you need to, and we did that, keeping things flexible and not, “Hey guys, we’re at the hour. We have to stop talking.” But if somebody was jamming, we let them jam. Right?
The next do is do allow for disagreements. Disagreement is where often decisions can get made. It’s often exposing things that may not be in alignment with each other, and that’s really important to discover. This is a perfect time to discover those things that different teams finally getting together in the same room to discuss different components and different things that may or be in alignment to get in alignment, and to have some agreement with eventually.
There were a lot of moments. I remember vividly where people on the team felt different ways about certain things and we could talk about them, right? And of course, because we set those ground rules, it wasn’t a yelling session and whoever yelled louder wins or anything like that. It wasn’t even like a voting situation, “Hey, who’s on team A, raise your hand. Who’s for team B, raise your hand.” It wasn’t like that. It was more of a conversation and allowing for empathy for the other parties, and listening to each other and all that great stuff is really, really key. So, do allow for that. It’s okay, and set that precedence that it’s okay to disagree.
Now, don’t go on unless you’ve got decisions made. At least something to go off of, because what you don’t want to do is waste time, and time wasted in these situations is when you discuss and you talk and you just go, “Okay, let’s move on to the next thing. I don’t even know where we’re at now, but we’re just going to keep going anyway.” You want to get to a point where decisions are made because that’s how you make progress, right? And that’s your job at these things is to come together to make decisions.
Now, the beautiful thing about the way Matt did it is he allowed for day one to be … kind of revealing his process a little bit here, but day one was divergence, right? Day one of our giant meeting was divergence, which means, let’s lay all the problems out on the line, all the frictions, all the challenges, the struggles, and then let’s all together, similar to a mastermind group, create ideas. And it was cool because we were getting ideas from different departments and different sections of the business that would’ve normally never even thought about those things, but we get different perspectives. We get more brains in the room and more opportunity for those ideas to come about, so that’s divergence. It’s coming from where you are to now diverging into many different possibilities.
And then day two was about decision making. It was allowing for each of those departments, if you will, to come in and start choosing the right decisions based on the goals and what was discussed the day before, to be responsible for those things, and then present what the decisions were to make progress. Right? And that was really cool, and that allowed us to, again, get the brain trust in there and come up with a whole bunch of ideas for all the different sets of problems and struggles, and to prioritize them as well at the same time. And then have an understanding that each team will make decisions on those things to solve those problems in the next day, and then, boom, we’re just not moving on. We are making decisions and making strides forward that we would’ve never done if we didn’t put ourselves in this situation.
And of course, again, it’s so much better doing it in person than having an eight-hour Zoom call each day, which I’ve had those. That was our team sort of retreat or meeting last year. And I remember, just because we were on Zoom, it felt like … I remember it feeling when it was on Zoom like, “Wow, this went by really fast.” But I think it went by really fast because we just knew we didn’t want to be on Zoom all that time. And you lose the opportunity to, during a break, just chill in the coffee shop next door, to chat about the families and how things … You miss out on those opportunities when you don’t meet in person.
Do have some fun. Schedule in fun time. We scheduled in, of course, the Rocky Mountain National Park, where we went hiking and we had a nice picnic and lunch together and explored a little bit, and that was super cool and fun. And then we also ate at some really good restaurants and had some drinks together. Part of the group who wanted to stay out a little bit later, myself included, went to The 1UP barcade. That is, in fact … If you’ve never heard of these things, I mean, they’re in many different cities. Look them up, Barcade, so Barcade. I’m not saying “Go out and drink.” I’m just saying these things exist, and some of us chose to go out and play games. That’s what I did.
Imagine an arcade, but there’s a bar, a barcade. And there’s bigger, more corporate versions of these things, like Dave & Buster’s, if you’ve heard of that before. But this is more of a … It looks like an old-school arcade with standup machines and pinball machines. It’s not the ticket games or anything like that. I mean, there are some of those, like basketball and skee ball, and we, I think, played skee ball for over an hour and a half, or something like that. We were all trying to be each other’s scores, and it was only a quarter. It was so much fun and it was a great bonding experience. We had that time built in to go out and stay out a little bit later.
Jonathan, who’s on the marketing team, and I, we eat during the day. Before dinner, we would go out and scoot around. We would use one of the city scooters. I think it was either Lyft or Lime scooters was the brand, or Bird. I can’t remember. And we would just scoot around town in the city, and we were going 30 miles per hour on the street on these little scooters. It was just so much fun, and we had a nice time bonding together, and that was really cool.
If you have a leadership team, right, you have more of an executive level team, you want to make sure that you also offer some time for just the executive level team to get together. We did that the night before we started, so the day everybody flew in, which was Monday, and myself and a few other team members, Matt and Jay and SJ, we got together and talked about what our goals were for the week, and what we hoped to achieve and what we were excited about. And just, again, got to know each other and made sure we were all on the same page.
But we also had fun doing it, and we went to this really cool speak easy. I make it sound like all we did was drink the whole time. We didn’t. I’m just saying, these were the places we went to. Death & Co was the name of the bar, if you want to check out. It was a really exquisite, really cool, new looking, fresh, modern contemporary bar with some drinks I’ve never even heard of before, can’t even pronounce. And again, a time for the leadership team to get together and discuss and get on the same page, and share vision goals amongst each other that we could then dispel down to the team later.
Don’t overwhelm. It could be very overwhelming just by the nature of all of it. But then I know there are some teams out there who use this time to do hardcore workshops about personality tests and, “Hey everybody, okay, overnight, you’re going to read the first three chapters of this book, and I want you to come in the morning with a paragraph describing how you feel about it, and we’re all going to share it with each other.” Yeah, we could have done those things, and we have done those kinds of tests before, although not during the retreat. We usually do those things after or before, and then come together during those retreats to discuss and learn more about each other in that way, i.e. the 16 Personalities Test or the Enneagram Test. Again, we already knew that everybody’s brains were going to be fried, so adding more, right? Sometimes less is more, but don’t fry everybody’s brains. All right? Don’t fry everybody’s brains.
And then finally, what’s really important to do is to allow for some time on the other end of the retreat to just decompress, to recover, and to just have people be with their families again. Right? I mean, here’s another do, do thank the spouses of everybody on your team. We made sure to just acknowledge those people because they are spending extra time with the kids, right? They’re there by themselves at home, or they’re working double time to be able to support us who are meeting together, in this case, Denver.
And I know for example, April, it just so happened that this was a week where there were half days during school, of course, the time I was out, and she handled it like a champ. And she had some meetings to go to and hula practice and LEGO league practice situation that she had to manage all herself, and she stepped up and she was able to do it. I knew she could, but I also have to realize that that was more work on her end because I was here in Denver. And I could have easily said, “Oh, but we’re doing this for business,” right? And that’s a card that’s very dangerous to play because that doesn’t necessarily make up for anything.
In fact, yes, I got to do business and drink from a fire hose and get super overwhelmed with a lot of things over the week, but I also got to have fun. I also got to go to an arcade. I also got to have these amazing dinners and have some drinks with some friends, and she’s at home taking care of the kids, so I have to acknowledge that, and I have to just, again, always, every time I have the opportunity to give her a shout out and thank you. Because she’s truly the backbone of the family and who allows me to do all these things and allow me to have peace of mind while doing them, so thank you to April, and thank you to all the spouses out there. The entrepreneur spouses, here’s a glass, raising it to you, clink, appreciate you for all you do for all of us.
All right, so those are the dos and don’ts of the retreat, just kind of off the top of my head. I hope you enjoyed this episode, follow-Up Friday. We do have some fun, interesting follow-up Fridays coming up. In fact, we’re going to be running an experiment really, really soon. You’re going to know exactly when that happens, because I’m going to ask you for feedback on it. But as we always do here, we’re always experimenting. We’re always adjusting pivoting, trying to do things even better. And so, hopefully, leading by example and you can do the same. So cheers, thanks so much for listening in and here’s to you and your teams or future team, and all the success you’re going to have, especially going into 2022, which is just right around the quarter. How insane is that? Anyway, thank you so much. Peace out, take care, and as always, Team Flynn for the win.
Thanks for listening to the Smart Passive Income Podcast at smartpassiveincome.com. I’m your host, Pat Flynn. Our senior producer is Sara Jane Hess. Our series producer is David Grabowski, and our executive producer is Matt Garland. Sound editing by Duncan Brown. The Smart Passive Income Podcast is a production of SPI Media. We’ll catch you in the next session.
