The Importance of Leadership Offsites

Sei-Wook Kim (00:02.165) On today's episode, we're talking about leadership offsites — 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. Peter Kang (00:28.000) All right, Sei-Wook, so we're here today in person — not our leadership offsite, but this is a fitting topic. Let's dive in. Let's first set the table for what offsites, leadership offsites, especially in the context of an agency business, are and what they are not. Sei-Wook Kim (00:44.000) The thing to focus on is leadership offsites aren't really for the work that you should do in the normal course of the day. It's the hard decisions that, while you're working with your team and with clients, are the discussions that aren't being had. So it's not really a quarterly review of what's going on in the business. It's really having a specific set of topics that you can focus on with your team. Peter Kang (01:05.000) Yeah, and the goal is higher quality conversations. These things hopefully lead to clear priorities. You'll be able to resolve some tensions that might be hanging around. There's also shared understanding — and this is something we'll come back to a lot — of what matters and what doesn't, and also this short list of next steps, the decisions and commitments you can follow up on. Those are the hallmarks of a high quality offsite. And especially once the leadership team goes beyond the founders, and even when it is just the founders, alignment isn't automatic. You have to be a little bit more intentional about it. It really is an investment in the relationship among the leaders. Don't think of it as just another meeting — it's a big deal. So let's kick off with some core principles we learned by trial and error. Number one: preparation really does beat improvisation. You can't just block off time on the calendar, show up, and think you'll wing it. Discussions are going to meander. It's just going to be an inefficient use of time. The other part is being explicit about the outputs — is this time for reflection? Time for alignment, decision making? It could be all of those things, maybe some idea generation, but with thorough planning you at least understand what you want out of this. And then creating an artifact is a big one. Just because you had the meeting and you feel good, if there's nothing to document it, it can be quickly forgotten. But if you have something coming out of it, that's huge. Anything else? Sei-Wook Kim (02:22.506) Full buy-in. For everyone on the leadership team, making sure that you're present, you're not distracted, and you come prepared with whatever's needed for the discussion. Even one person being half in really distracts the whole group. That's funny because there's also the prep work that you demand of the people coming. But I remember, especially at Barrel, it would be the four of us in a leadership meeting and we'd have our laptops open — we'd have to turn our laptops around and show everyone that you had no other... close all your tabs, close emails, close Slack, no messages going on. You just have to be basically offline to really focus, and you have to commit by sharing your screen. Peter Kang (03:05.000) And the last thing is don't overpack the agenda. We learned this lesson over time. You have to have a focused set of things you want to accomplish, and you have to leave time for reflection and discussion. Don't try to stuff too much in. Cool. So maybe we can share the simple structure we ended up evolving to — a few different components, but this is a good structure for anyone thinking of doing an offsite or wanting to improve their offsites at their agencies. Sei-Wook Kim (03:30.000) Yeah. The first part we'll call a look back — what went well, what didn't go well, what was surprising about the past quarter or period of time. And then really a time for reflection: what do we learn as leaders? What are the big things we just avoid talking about because we didn't have time or they weren't a priority? Or even looking ahead from that reflection, what's something we could fix, or what would we do differently? It's a look back, reflection moment for the team. Peter Kang (04:05.000) And for that, we really do ask people to come prepared. It's not something people are going to be asked to improvise on the spot — we want well considered answers. We'd spend at least a good 15 to 30 minutes, depending on how many people are there, listening and hearing how people answer some of these questions. Some of this could be a lens for the future discussions to come, but it's more just setting the table. Sei-Wook Kim (04:30.000) We mentioned tension before, and part of what you can pick up from this exercise is what's on people's minds — what's their perspective on the past year, the past quarter. You can pick up on the language, and those are good signals to later double-click on and revisit together. Peter Kang (04:48.187) Yep. The next section we'll call learning together. For us, that was reading books together as the backbone of how we learned and built some shared language. And it was required reading — it wasn't optional where certain members of the team could come prepared and others less so. On a quarterly cadence, we had a specific book, sometimes two books, and everyone made the time to read, take notes, and work through a bunch of prompts we had. The preparation is everything for that discussion. And I was really close to this because it's my favorite part of our offsites. We picked books that a lot of times were about business, but sometimes were more about personal development — a good variety. But what was most important about reading these books together was the shared immersion. I know this happens a lot: if I read something and I'm excited about it and go to you, but you haven't read the book, you're just not going to get the same thing. You might hear it and think, oh, that sounds interesting, but you're not going to get as excited as I am. And some of the language I'm using might be a little foreign because you haven't immersed yourself in it. What we found was that as a leadership team, when you read a book together and really spend time with it — we're talking hours over the course of a few weeks, maybe a couple of months — you become ingrained in that language. So when you had that moment to sit down and talk about the book, you had that shared language. And you take that dynamic and do it over the course of, for us, about seven years, one to two books every quarter. I think it ended up being over 40 books that we read together. These things have a magical way of compounding — you start connecting concepts across books, and you have this much more sophisticated dialogue, all built on that base of shared language. Sei-Wook Kim (07:30.000) Yeah, a really important part of all of that was taking the time to reflect on how it affected you personally — any takeaways that affect your life or your business and how you approach your team. Over time, you read another book and it changes your perspective on a prior one. You see the common themes across multiple books, and that evolves how you interact as a leadership team. That shared language gets richer and richer. Your team gets closer and you almost have your own way of talking — your own secret language of sorts — but you're on the same page with what's going on. Peter Kang (08:05.000) Yeah. And a practical takeaway: what we would actually do is spend the first hour of the book discussion just sharing what we highlighted and going through why each person highlighted what they did — just hearing what resonated with them. Doing that in itself was such a huge way to get value out of the book. And from that, we had an artifact where you could see the theme, the quote, and who selected that quote. By the end, you have this huge map of the book — synthesizing from a long book the key five to ten themes and the quotes that really resonated with the team. It's really helpful to have that artifact to look back on. All right, do you want to take the last part? Sei-Wook Kim (09:28.649) Yeah. The last part is thinking about where do you build together as a leadership team? You've discussed the challenges, you've had the shared language exercise together. Now it's really aligning as a leadership team: what are we going to focus on for the next quarter and next period of time? What are we going to say no to or back-burner? What are we really doubling down on? And then what are we going to change — how do we operate differently, how do we interact with our team? What work are we going to take on and not take on? How are we going to grow and maybe make investments in hiring for a different role? It's the exercise of looking back a quarter from now and saying, where do we want to be? Peter Kang (10:05.000) Yeah. We tried so many different types of exercises to unlock this segment of our offsite, because you do need some kind of activity or prompt that gets your brainstorming and idea juices flowing. Sometimes we got really personal with it — one of the big takeaways from all that reading was that a great business first starts with personal mastery as a leader. So one of the exercises I remember was this future self writing, where we'd come prepared with narratives: it's a year from today, you're reflecting on the year, and you describe everything that transpired in your life and in the business. It's a visioning exercise, but it makes it super personal. I remember this was at a time when some of us were having kids for the first time, becoming parents, along with all the things going on in the business. It was really cool to hear some of the things that came out of that exercise. Sei-Wook Kim (11:00.000) And again, to the lens of preparation — everyone has to take the time to really think and stretch their mind into some imagination of where things could be, unrelated to exactly where we are today. Sometimes we went even further, five or ten years out, not just one year. It really makes you think about where you're going to be, and then you can think about the steps to get there. Peter Kang (11:20.000) Yeah, those things are such a good use of time. Another one that's a bit more business practical: we've done exercises where we'd learned about the flywheel concept in business and asked everyone to come prepared with their take on what the flywheels are within our business — draw some diagrams, walk people through it. That was always fun because you realize everyone has a slightly different mental model of how the business works. That opens up discussion for a lot of interesting things. And even within specific disciplines — say engineering or creative design — what are the flywheels in that part of the business, and how does that bubble up to the overall picture of the agency? Maybe one more exercise — anything you want to throw in? Sei-Wook Kim (11:48.815) Depending on the phase of the agency, it's good to reflect on mission and values. Early on in our journey, every six months, every few months, it was really just making sure: are we clear on what's our mission, what do we care about, and has that changed? Because in the evolution, and even later on as an agency, things could change pretty quickly. Having a reset there, going through the exercise, having each person come with prep work on these topics and then discussing it together to see where it overlaps — and where the differences are. Peter Kang (12:20.000) Yeah, and actually doing it multiple times helped make the final results more durable. Some of the values we came up with — this was probably the fourth or fifth time we'd done that exercise, maybe three or four years in — looking back now, the team at Barrel is still using those same values we defined years ago. Because a lot of that had been time tested, stress tested in a really big way. Okay, so maybe we could hit on some stuff that didn't work as much — things we changed over time. Sei-Wook Kim (14:12.518) We mentioned this before, but if you have too much in the schedule and not enough time, the discussions end up too shallow. You want to leave breathing room — if there's a conflict you've got to work through, you need the time. When else are you going to have those discussions? And no follow-through and no documentation artifact is a killer. Did it even happen at all? And preparation — making sure everyone's bought in and spends the time to do the work, whether it's reading a book or writing some things. Some of the lazy offsites I can remember are just showing up and doing a SWOT analysis together or having a big vent session as a group. You think it's okay in the moment because everyone's talking, but in hindsight you go, that time could have been better spent. Peter Kang (15:00.000) Last point is too many initiatives coming out of an offsite. You go into these thinking you're going to nail your priorities, but you have to be careful — from our experience, you can get overly ambitious with so many things to fix and end up with a laundry list. EOS has a structure with rocks and things that gets people thinking they always have to have something going on, but a lot of times it doesn't have to be so many things. That's something we've learned over time. Yeah. We've done this over many, many years, and it's one of the things that has really helped build strength and relationships within the leadership team. That personal relationship is a big part of it, but it's also really motivating to take a step back, learn about other businesses through your reading, apply it to your business, and see development. That rhythm and that compounding growth in language and the shared reference of what you've built over time — it's really empowering and exciting to see with the team. Sei-Wook Kim (16:33.593) Yeah, it's rewarding. And just to wrap this up: leadership offsites can come in many flavors. You don't have to have an office — you could go somewhere exotic. Superficially it might feel like you're taking a break from the daily grind, but it's actually not. As we mentioned, it is a big investment in the alignment of your leadership team, making sure you're clear on where you're headed and that everyone works well together. With that, we hope you invest the time in having some wonderful offsites, and thank you for joining us. Peter Kang (17:05.000) Thanks.