MBA1296 4 Takeaways From Our First Team Retreat
2 Feb 2026 · 13 min
Omar Zenhom shares lessons from his team's week-long retreat in Bali. Set a clear goal upfront, run alignment sessions so people aren't guessing what others know, use personality tests to understand differences, and plan months ahead with logistical help. The retreat cost about $5,000 per person.
Questions this episode answers
2019-06-27
Bali, Indonesia
One week
About US$5,000 per person (including airfare, insurance, accommodation, meals, activities).
About 10–11 months (planning began around July of the previous year).
Chapters
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And yesterday Nicole, I sat down and had kind of a debrief and a brainstorming session of what went wrong, what went right, what we can do better next time while we're still fresh in our brain. So in today's episode I want to share with you the four big takeaways. Of course there's going to be little things we could do better, little logistic things that we, you know, thought didn't go so right. But I want to share with you more of the bigger things that I got from this experience. So if you're thinking about doing your first team retreat or any team retreat to consider these things, team retreats are great. Whether you have a remote team or a physical team, it gives you a chance to really get to know your team on a personal level and a professional level, working on projects, team building activities. Plus, it's a whole lot of fun for everybody. So in today's episode, I'll be sharing with you my four biggest takeaways. Can't wait to share them. Let's get into it. Let's get down to business. So we had our first team retreat. Just got back. You might hear in my voice that I'm a little congested. And yes, I did get sick. I actually got hit really hard with a cold towards the end. Maybe it was the stress, maybe it was just being on 24 7. We'll talk about that in a moment. But got back super happy with the result of the treat. We feel like everybody had a great time, but we also learned so much about each other as a team. There's so much I can go through about how much fun it was and how it was great to meet everybody in person and get to know them personally. But I'm gonna go big picture in today's episode and share with you my four big takeaways. So takeaway number one is Nicole and I. When we started this retreat, we had a clear goal for the retreat. This was very, very helpful. I think the retreat wouldn't be as successful or as enjoyable if we didn't have this laid out at the start. Number one, we had a clear goal for ourselves, but we communicated this goal to our team before the retreat in team meetings and at the start of the retreat in, like an orientation session at the start, where it just frames the week. It just tells everybody, hey, this is why you're here. This is why we're doing this. And this is our collective goal. It really helps you frame every action, every activity. Because when you're planning this retreat and planning what you're going to do on the retreat, you're going to ask yourself, hey, does this help us achieve that one clear goal? And that clear goal could be anything that you need to achieve in your business. So I'll give you an example of our clear goal, our goal, because it was our first team retreat, and this is the first time many of us were meeting each other in person. Our one goal is to get to know each other a bit better. And we kind of elaborated what that means. Like, how do we like to work with each other, our personalities, our working styles, get a little background about who these people are, you know, and just enjoy each other's company. So we wanted to build activities around that that allowed us to collaborate and put our Brains together and have fun together. Now, our goal may be different for next year, but for our first retreat, this was really the goal. Now, it doesn't mean that it was just like a free for all, and everybody just did what they wanted. We had a very clear agenda, and there was a lot of fun, a lot of excursions and activities and dinners and drinks and a lot of good stuff. But every activity was purposely crafted to serve that goal. Now, if we didn't have a goal, it would be hard to really know what to do on this retreat. It was a week long. People were traveling, you know, maybe even a day and a half to get to Bali. So one of the fears Nicole and I had was if our team came and it was just a big waste of time, we wanted to make sure that they felt like it was thought out, that every activity had purpose and was worth their time and effort. Yes, this is sort of like a working holiday, but we want them to go home feeling like they've grown as a person, as a professional, and gotten to know their teammates a bit. So having that clear goal really helped lay out the agenda, lay out what we're going to do, the purpose, and also communicate that clear goal to our team at the start. So that was takeaway number one. That really helped us. Now that it's all over, that first retreat, I could see how beneficial it was. Takeaway number two, do not assume. I learned through the week, working together, having fun together, getting to know people on one on one chats, that I was making a lot of assumptions about people that were incorrect, which is not so good as a leader of the company. And I'm going to get in front of her right here and say, yeah, I made some assumptions about people that were wrong. Now, these are not good or bad assumptions, but you assume, you know, that everybody in your company knows what you know, and it's not true. And I went in to the retreat saying, you know, we don't want to assume everybody knows what we know either. So we went to the retreat knowing that. So we had sessions that kind of covered the history of our company, where we've been, where we are today, and where we're going in the future. You can't just assume everybody knows the history of your company or what's going on, because people join at different times. Some people have been with you for four years. Some people have been with you for one month. Please. So we had a session like that. We also had a session on learning about our customers, understanding who we serve. You can't assume that your engineers know everything about your customers because they don't really interact with them as much as customer service does. So we try to not assume as much as possible. But even though we had sessions like this, I in my head assumed they were further along in their understanding than they actually are. Now that's my fault, not their fault. You know, they're doing a great job, they're working hard, they're focusing on their strengths and what they do. They're. But I learned, wow, we need to do more of that outside of the retreat. We need to make sure that people understand what's happening. When we launch a new product or new service, we kind of maybe have a chance to kind of regroup and have a all hands meeting and reiterate. Now, a lot of us resist this because we feel like some people on our team already heard this or know this, so it might be boring for them. But hey, there are people on the team that it's not boring for them. It's new information and you need to do what's best for the whole team. So my advice, my takeaway is go into your retreat with no assumptions. Don't assume anybody knows anything. Don't assume people like a certain thing or don't like a certain thing. If you can, survey your team before the retreat, ask them some questions and go in making sure everybody's on the same page. You want to make sure that everybody is on the same page with every aspect of your business. You know, whether your support team understands how an actual feature is built. We actually went through a team project and I think a lot of our support members were like, wow, I didn't know what it takes to kind of of build a piece of our software, a piece of our program. And it was very eye opening. So I think assumptions are bad. Do not assume. Make sure everybody's on the same page. Takeaway number three. Now, this is going to sound obvious, but it's really important for you to remind yourself of this before and during your retreat. And that's everyone is different. And of course, that's human nature. People are different. Some people like certain things. Some people are early risers, Some people like to stay up at night. Everybody manages their energy differently. Some people like to work in large time chunks. Some people like many breaks. Some people express themselves in different ways. Some people like to kind of be outspoken. Some people like to express themselves, you know, in written form. Everybody is different. And you start to realize that in person because all that kind of stuff gets hidden away when you're working remotely, when you're working via Slack or via Basecamp and you're sending emails or messages and everybody kind of manages themselves on their own time, their own clock, in their own respective home offices, right? But when you're all together in one location, you're doing so many activities together, you're following the same schedule, you start to realize, wow, I have a very diverse team and that's good. And I think you should celebrate your differences as a team. You really should actually share those differences, make sure everybody knows how we're different. One of the exercises we did is a personality test. It's a very simple way workplace personality test to learn more about the different personalities that we have on our team. It was a very good exercise and we would refer to it throughout the retreat. It was a color personality. So, you know, somebody's personality might be a yellow or a red or a green. So after we did that kind of assessment, everybody knew who they were. And throughout the retreat, like, oh, you're such a red or you're such a green or you're such an orange. That's the point of learning what that's all about. Now, of course, we all understand that that stuff is not an exact science, but it gives us a general idea of everybody's personality. And what I love about it is it showed how diverse our team is and how everybody has strengths and everybody has, you know, areas that we need to focus on or areas you need to be aware of. So don't shy away from the differences in your team. Celebrate them, be aware of them. And now that I know the differences, I can plan a better retreat next year with those differences in mind. My fourth takeaway from our team retreat is that this takes time and it needs help to do this right this time around. Nicole and I did everything when it came to planning this retreat. Now this is like running a seven day wedding or something, like pulling off an amazing event because you got to take care of flights and accommodations and food and meals and restaurants and reservations and insurance and the schedule and being on and doing the sessions and giving speeches. I can go on and on. But the point here is, is that it took us about 10 months to plan this. I mean, from I would say, July of last year, we started planning. So maybe even like 11 months. And as we got closer and closer, we were working more and more on this project, the team retreat. But it did take a lot of our time. It did take a big chunk of our attention. And we realized, you know what, this is good that we did it ourselves the first time around. We learned a lot. But we are going to need some help. So Nicole and I are dedicated to hiring somebody to help us. Hiring an executive assistant to help us with the logistics of everything. A lot of the work is admin based that an EA and executive assistant can do, whether it's reservations or scheduling or communication during the retreat, you know, communicating with the team, updates the schedules, answering questions, helping them check into the rooms. You know, Nicole and I were doing all of that. So getting some help was something that we realized we need to do immediately. In fact, we're trying to go through that process of hiring somebody right now because we're gonna have to start planning next year right now because of course, it takes time. So don't think that this is something you could pull off, you know, with a month of planning. No, you need some time. You need to make sure people can make the actual retreat. Their passports are in order that you make the reservations. You choose the right location for your team. You know, we surveyed our team, we give a feedback form at the end of the retreat and that is gonna form a a lot of what we do next year. And as you continue to do your annual retreats, it's expected that your team's going to grow. So there are going to be more people attending and it's going to get more and more complicated. So getting that help, getting an assistant, getting somebody to do something. There are companies that we know, like Buffer, who have a full time person who just takes care of their team retreats. I believe they do two retreats a year. But her sole job is to plan these retreats, scout locations out, organize everything so you definitely can benefit with somebody who's focused on this full time.
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So was our first team retreat worth it? Did we get a return on investment, so to speak? I want to first say that running a team retreat, if you do it right, if you treat your team right, if you do activities and excursions and it's a really nice location, it's going to get costly. It's expensive. It's actually an expensive activity. Nicole, I knew going in because we spoke to other remote teams that run retreats, you know, how much this would cost and if you're wondering how much, well, we did ours in Bali, Indonesia, so a lot of people were flying from different parts of the world. We spent a week in Bali. We covered all meals, all activities, excursions, things like adv and bike riding and cultural tours. We had a lot of fun. But it cost roughly US$5,000 per person to do this retreat. When you factor in airfare and insurance and, you know, accommodation, food, everything that we just kind of mentioned and other things that I can't think of off the top of my head, that's really how much it costs. So, well, is it worth it? Well, I believe it's really worth it. I think we got a huge return on investment because our team really is a cohesive unit now. People know each other, they're friends. We're going to save a lot more time and money in the future, but because of that, we're going to be more efficient. And to be quite honest, we do these things because we value our team and we want to treat them well and we want them to stay for the long run. We want them to feel committed. So we want to show our commitment by, you know, spending on them on something like this once a year. It's expensive to find new employees, new teammates, you know, it's doable, people leave and all that kind of stuff. But I rather not have to deal with that. I rather have people that are committed for the long run, people that, you know, see your vision, are bought into it and are willing to, you know, put the work into it to see it happen. So we are looking forward to doing our next retreat next year around the same time, maybe a little bit later and building upon what we've gained this year. I hope today's episode was helpful, if it was let us know in an iTunes rating and review. It takes two minutes and it lets us know what you love about the show. Don't forget to hit subscribe, because by hitting subscribe, you get the next episode downloaded to your device automatically so it's ready for you to listen whenever you're ready to listen. We're on Stitcher Radio, Apple Podcasts, Overcast, Spotify. Every single app out there just hit subscribe right now. Before I go, I want to leave you with this. I am tired. Retreats are tiring. Like I mentioned, it's a lot of work. You know, we're going to get some help, so it'll be a little bit better. But plan for this. You know, I'm coming back and I got a busy schedule. I should have scheduled less. Coming back knowing that I'll be a bit tired, a little bit worn out a little bit, maybe even under the weather. So my advice to you is understand that this is going to take a lot out of you, a lot of energy. The traveling itself takes a lot of energy. So plan for it, and that way you can come back and ease into things again. All right? Hope that helps and hope to see you in tomorrow's episode. Free ride Friday. I'll see you then. Take care. USAA knows dynamic duos can save the day like superheroes and sidekicks or auto and home insurance. With usaa, you can bundle your auto and home and save up to 10%. Tap the banner to learn more and get a'@usaa.com bundle restrictions apply.
