The Importance of Leadership Offsites

On today's episode, we're talking about leadership off sites. Why they matter and how to run them so they actually improve alignment, strengthen the leadership team, and produce decisions you can carry into next year or quarter. We'll share the structure we've repeated and refined over the years, the specific exercises we've used, and what worked, what didn't, and what we changed over time. All right, say we're here today in person, not our leadership off site, but this is a fitting topic. So, yeah, let's dive in. Let's first set the table for what off sites, leadership off sites, especially in the context of an agency business, are in what they are not. Yeah, I think to focus on is leadership off sites aren't really for the work that you should do in like a normal course of a day. It's like, what are the hard decisions that, while you're working with your team with clients, it's the discussions that aren't being had. So, it's not really like a quarterly review of what's going on in the business. So, really having a specific set of topics that you can focus on with your team. Yeah, and really the goal is higher quality conversations and these things hopefully lead to clear priorities. You're able to resolve some tensions that might be hanging around. Also, some shared understanding, and this is something we'll come back to a lot, is what matters and what does it, and also this short list of the next steps, the decisions, the commitments you can follow up on. So, yeah, I think those are kind of the hallmarks of a high quality off site. Yeah, and especially once a leadership team goes beyond the founders, even when it is just the founders, the alignment isn't, you have to be a little bit more attentional about it. It doesn't just happen automatically. Yeah, it's really like an investment in the relationship among the leaders. So, yeah, just don't think about as just another meeting. It really is a big deal. Yeah. So, I think again, be intentional. What do we want to get out of this time together? Yeah, yeah. Alright, so let's kick it off with some maybe core principles that we learn, you know, just kind of by trial and error. So, number one, I think is, yeah, like preparation really does beat improvisation. So, you know, you can't just show up. You can't just block off time and counter show up and think, hey, like, well, wing this. It's just, you know, the discussions are going to be in there. It's just going to be an inefficient use of time. Yeah. The other part is just being a bit more explicit about the outputs. You know, is this kind of time for reflection? Is it time for alignment? Decision making? I mean, it could be all of those things. Maybe some idea generation, but, you know, with thorough planning, you get to at least kind of understand what you want out of this. Yeah. And then, you're just creating an artifact is a big one. I mean, I think, you know, just because you had the meeting, you feel good, and then there's nothing to kind of document it. It kind of, you know, can be quickly forgotten, but if you have something coming out of it, that's huge. Anything else? Yeah, I think, um, full buy it. I think for everyone on the leadership team, making sure that you're your present, you're not distracted, and you come prepared with, you know, whatever it is for the discussion. Yeah. So, yeah, if you, if one, even one person being like half in really distracts the whole group. That's funny because I mean, there's also like a prep work that you demand out of the people coming. Yeah. But I remember like, you know, especially at barrel, when like it would be like the four of us, uh, the leadership meeting, and you know, we have our laptops open. Yeah. Remember, we have to turn our laptops around and show everyone that you had no other clothes on your set, clothes, emails, clothes, like no messages going on. And you just have to be basically offline to, to really focus. And you have to commit by sharing your screen. Yeah. And I'll say the last thing is, um, don't over pack the agenda. I think we, we learn this lesson over time of, you know, uh, you know, you have to have, you know, a focus, you know, set of things that you want to accomplish for that. And, um, you have to leave time for reflection, discussion, and yeah, don't try to just stuff too much in the agenda. Yeah. Yeah. Cool. All right. So maybe, we can kind of share the, the simple structure that we ended up evolving to. And, uh, you know, maybe a few different components to this, but this is kind of a good structure maybe for anyone think of doing off-site or wanting to improve their off sites that their agencies might, might find helpful. Yeah. So the first part we'll call like a look back on, um, you know, what went well, what didn't go well, surprising, um, you know, about the past quarter of period of time. And then, you know, really a time for reflection on like, you know, what do we learn as leaders? Um, you know, what are like the big things that we just avoid talking about is we didn't have time or wasn't a priority. Yeah. And for that, we really, um, do ask people to come prepare. Yeah. So, you know, it's not something that, you know, that people are gonna, um, be asked in proper, uh, like, you know, improvise on the spot. Um, but what we want are kind of well-considered answers. So, yeah, this is, you know, I think we would spend at least a good 15 to 30 minutes, depending on how many people were there of like, could it listening and kind of hearing how, uh, people answer some of these questions. Yeah. And some of this could be a lens for the future discussions to come, but it's more just semi-table for here at the, uh, yeah. I mean, we've had, we've had much attention before. And like, you know, part of the things that you can pick up from this exercise is kind of, yeah, what's on people's minds? Like, really, you know, how, how have there, you know, what's their perspective like all, you know, the past year, the past quarter, uh, you know, we're like, you can pick up on the language and those are good signals to later, you know, uh, double click on and kind of, you know, revisit together. Yep. The next section, uh, we'll call, uh, learning together. Uh, so for us, that was, uh, really bucks together as kind of the backbone of, uh, how we learned and how to ensure language. And, uh, for us, it wasn't, it was required reading, you know, it wasn't like a nice ad where certain members of the team could, could, uh, come prepared and others less so. And, um, basically what we did, you know, it's quarterly cadence for us. We, um, you know, had a specific book, uh, or if it was a two books, yeah, sometimes you had two books and really decades of time, um, everyone made the time to read, take notes, and there's a bunch of prompts that we had as well. But it's, um, yeah, it's, the, the preparation is everything for that discussion. Yeah, you know, uh, and, you know, I was, I was really close to this because this is my favorite part of our off sites. And so, um, the two, you know, we picked books that, uh, you know, a lot of times were about business, but sometimes they were more about kind of like personal, uh, development. Um, and so, you know, we had a good variety of things, but what was most important about, uh, reading these books together, uh, was that, you know, and, and maybe like, you know, just, I know this happens a lot where, if I read something and I go, I'm excited about it and I go to you, but you haven't read the book. Yeah, like, you're just not gonna get the same kind of, you know, like you might hear it be like, oh, that sounds interesting, but you're not, you're not gonna get excited about it as I am. And, the language I might be using to describe it from that book might be a little foreign team because you just haven't diverse yourself in it. Yeah. So what we found was as a leadership team, when you read a book together and really spend time, and this has been talking hours over the course of, you know, a few, few weeks, maybe a couple of months that you're reading the books, um, you, you become kind of ingrained in that language. And so when you have that moment to be like, hey, let's talk about the book. You had that share of language. And so you take that dynamic, and then you do that over the course of, you know, for us, it was seven years or so of like, few books, you know, one to two books every quarter, you know, I think I'll end up being over 40 books that we read together. These things have a magic way, a magical way of like compounding, because you're like, oh, this concept was something that came up in this other book and, you know, like, and you know what, this book has an interesting take on it. And you start to kind of have a much more, you know, sophisticated dialogue with what you've read. And then at the same time, you had that base of share language. Yeah. I think really important part of all of that was taking the time to reflect on, you know, how that affected you personally. If there are any takeaways that affect your life and even your business and how you approach your team, and all of that, even over time, you read another book is like, oh wow, that changed my perspective on this factor. Or you see the common themes, right, across multiple books. And really that kind of evolves how you interact as a leadership team. And it's almost like, so much, yeah, that share language is really important, because then like your team gets closer together. We almost have our way of talking. It's like our own secret language of sorts, but it's a you're on the same page with what's going on. Yeah. And just to something practical take away was like what we would do actually is spend the first, you know, hour of the book discussion, just the sharing what we highlighted in the book. And just that exercise of like, hey, why did you highlight that? And yeah, each person kind of talking about what resonated with them that just doing that in itself was such a huge way to get value of the book. Yeah. And from that, we actually had an artifact where all of the clips, you know, you could see our here's the theme, here's the quote and then who, you know, saw that good echo. And then by the end, you have this huge map of like the book. And it's really synthesizing like, yeah, from this long book, you know, what are like the key five to turn themes and what are the quotes I really, you know, resonated with the team. So that's really helpful to have that artifact to look back on. Yeah. So the last part is thinking about, you know, where do you kind of build together as a leadership team? You know, you, you know, really aligning as a leadership team. Like, what are we really going to focus on for the next quarter and next period of time? Like, what are we going to say no to a back burner? What are we really doubling down on? And then what are we going to change? You know, what are we like, how do we, um, operate differently? And how do we interact with our team? Like, what work are we going to take on? I've not taken on how are we going to grow and maybe make investments and hiring for a different role? Yeah. And really we tried so many different types of exercises to unlock this, you know, this kind of segment or component of our off sites. Because, you know, you do need kind of an activity or prompt that gets your, you know, kind of brainstorming or idea, you know, juices flowing. And so, you know, there are some ones, sometimes we get really personal with it because, you know, I think for reading all those books, like one of the things takeaways was like, hey, a great business, you know, first starts with kind of personal mastery over yourself as a leader. And so, you know, we don't have a lot of exercise around that. So one of the things I remember was we do this kind of like future self-writing where we, you know, we kind of come with prepared, you know, really like narratives on like, hey, it's a year from today, you know, you're kind of reflecting on the year and just describe all the things that transpire both in your life and in the business. And this is a powerful stuff because it really, it's a visioning exercise, but, you know, it makes it super personal. And I remember this, this was like at a time when like some of us were having kids for the first time to come to my parents and other kind of challenges in the personal life, along with like all the things going on in the business life. And it was like really cool to hear some of the things that came out of this exercise. Yeah. And I think again, like to the lands of, you know, preparation, it's everyone has to take the time, you know, after, you know, you go through the first part, you read the book, but this is something different where you're really thinking and stretching your, your mind into some imagination on like where things could be like unrelated to exactly where we are today. And sometimes we've gone even further five, 10 years later, not just one year. It really makes you think about like where are you going to be and then what are, and then you can think about what are the steps to get there. Yeah. No, those things are like just such a good use of time, I think. Another one that's a little bit more like business practical, we've done things where, you know, for example, we kind of learn about like a flywheel concept in business and we ask, you know, everyone to come prepare with, hey, when you think about our business, like what are the flywheels that exist within it and, you know, draw some diagrams and kind of lock people through it. And that was always fun because you realize like everyone has slightly different mental model of like how the business works. And so that opens up discussion for a lot of interesting things as well. Yeah. And even in, you know, for specific disciplines, say like for your part of your discipline, you know, let's say you're in this 12-regionary or creative design, like what are aspects of that part of the business that have a flywheel and how does that bubble up to the overall picture of the agency. Yeah. I think depending on the phase of the agency and, you know, it's good to reflect on mission and values, I think that earlier on, you know, we were in an easy journey. It's like every six months, every few months. It's just like really making sure that are we clear on what are, you know, what's our mission, what do we care about and how does that change because, you know, in the evolution, and even later on as the agency, you know, things can change pretty quickly. Yeah. So, I think, yeah, having a reset there, going through the exercise, having each person, again, come with some paperwork on these topics and then discuss it together and see whether overlaps and, you know, differences. Yeah, and I think the actual, actually doing it multiple times helped to actually get the final results being more durable. So, you know, like even some of the values that we came up with, let's say like three, four years ago, and that was probably like the, you know, fourth or fifth time that we did that exercise and, you know, looking back now, like, you know, today, like I was, like, it's still there. Like, you know, the team at Barrel was still using the same values that we defined years ago because like a lot of the time that were time tested, it was like actually like tested, stress tested in a real big way. And so, I think that was like, you know, time well spent. Okay. So, maybe just we could hit off some stuff that didn't work as much. And, you know, like, what are some things that we change over time? Yeah, I think we mentioned this before, but, you know, if you have too much in scheduling, not enough time, you just, you two shallow discussions. You want to leave breathing room for, if there is a, you know, conflict that you've got to work through, you know, just have the time because, you know, when I also, you know, have those discussions. Yeah, definitely. And I think, let's see, just, yeah, maybe we talked about kind of the the documentation artifact coming out of that discussion too, just like, yeah, no follow through. It's just like, didn't happen at all. Yes, I mean, you even remember. And then talk about preparation, but I think that's really key. Making sure everyone's bought in and when it spends a time and does the work to whether it's reading a book, writing some things. Yeah. And, you know, honestly, like, I think some of the lazy kind of off sites that I can remember is just like, you know, when you go, hey, let's just do a swap analysis together or like, hey, let's have a, hey, like what's not working? And you have like a big vent session as a group. It's just, yeah, you know, it's not the, like, you know, you think it's okay in the moment because like everyone's talking or whatever, but like in hindsight, you go, that like that time could have been better spent. Yeah. Yeah. Last point is, I think the too many initiatives coming out of an off site because I think, honestly, like, you go into these thinking, oh, yeah, like we're going to have priorities or whatever, but you just have to be careful. This is just from our experience, right? Of like, you know, just, you get overly ambitious with like, oh my god, we have so many things to fix and you have a laundry list. And, you know, not to, you know, I think EOS has like a structure with like rocks and stuff that like really get people thinking like they always have to have something going on, but a lot of times, you know, it doesn't have to be so many things. And I think that's something that also we've learned over time. Yeah. I mean, we've done this over many, many years. And, you know, it's one of the things that have really helped kind of build strength and relationships with the leadership team. And, you know, I think that's kind of one big part of it is building that personal relationship. But also, it's, you know, really motivating to kind of take a step back, you know, learn about other businesses that you're reading, you know, apply into your business and you see development and that rhythm and that compounding growth in that language and that reference of, you know, what you've built over time is really, you know, really empowering and really exciting to see with the team. Yeah, it's rewarding. And, yeah, and I think like, you know, just to wrap this up, you know, I think the leadership offsite, you know, it could be many flavors. You don't have to, you know, you don't have to have it in office. You could go somewhere exotic and all those things. So, so, you know, superficially, it could be like, oh, you're taking a break from the daily grind of work. But it's actually not. It's actually like, like we mentioned before, it is a big investment in kind of, you know, the linements of your leadership team, you know, just making sure you're clear on, you know, where you're headed. And, you know, it's just a way to make sure that everyone works well together. So, with that, you know, we hope you invested your time in, you know, having some wonderful offsights. And thank you for joining us. Thanks.