MBA2285 What Went Wrong & Right With Our Team Retreat
2 Feb 2026 · 15 min
Omar Zenhom reflects on his four-day team retreat in Cebu, Philippines. The food options and photoshoot fell flat, but karaoke and customer empathy mapping workshops bonded the team. Delegating logistics to his executive assistant Romina made the whole thing run smoothly.
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Hey oh. Welcome to the hundred arm building business insights every single day with our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of Webinar Ninja, an independent software company. I started my co founder back in 2014 and in today's episode you'll learn what went wrong and what went right with our team retreat. We just wrapped up our team retreat just a few days ago where we gathered every teammate from every corner of the world to spend a few days together to get to know each other, to bond, to work, to team build, to have a bit of fun. Running a team retreat is a lot of work. There's a lot of logistics involved, there's a lot of things you need to plan and look out for and it doesn't always pan out as you expect. In today's lesson, I'm going to share with you what went wrong. What are some of the areas we need to improve upon, some of the mistakes that we should avoid next time around as well as what went right and what were some of the huge wins from the team retreat. A couple of things about today's episode Number one, I'm doing this so that you can have a better team retreat than I had. Learn from my own experiences so you can do it better. We had a fantastic time. It was overall a success. But if I have learned anything in business is that if you share your knowledge, you can help other people share your experiences. You can help so many people that are going to go through the same thing as you are. The second thing about today's episode is this is not my opinion. This is not theory. These are not my gut hunches, right? This is based on feedback that we actually received from our team. Every time we run a tree or any kind of event, we collect feedback with a feedback form from our attendees. So this is a raw truth. And I decided to do this episode before I saw the feedback. So I got to live up to it. I got to, you know, just stand on my ground and share what I learned. So let's get into it. Let's get down to business. This episode is sponsored by Time Doctor Measure and improve productivity wherever your people work. With accurate and employee friendly time and activity tracking, you can empower your staff to work from the office, home or anywhere else with total peace of mind, boost productivity and enable your teams to get better together with Time Doctor in your tech stack. I highly recommend Time Doctor because we're using Time Doctor. We rolled that Time Doctor over a month ago and it's going amazing, so why wait? Join me and over half a million happy customers and unlock the power of visibility, accountability and productivity with Time Doctor by starting a free trial today. Visit the Time Doctor website over at www.timedoctor.com to get started again. That's timedoctor.com Our 2023 team retreat was so important. It was so critical for our team because it was so long awaited. Our last in person team retreat was in 2019. We planned to go to Thailand in 2020, but we all know what happened in 2020. Our last team retreat was virtual online. Back in 2021, we decided to do a team retreat regardless of COVID 19, even if it meant just doing it over video calls. Throughout a week. We did some sessions, had some fun, had some friendly competition and team building and it was great. But it just wasn't the same as doing an in person retreat. There's a different level of camaraderie and friendship that you build with somebody when you meet them in person, when you spend time with them in person. And that's why we were so looking forward to this team retreat. This time we decided to do it in Cebu, Philippines. We have team members that live in different parts of the Philippines that came over to Cebu Also many other team members coming from other countries to make this team retreat happen. And just to give you an overview, the team retreat was about four days, starting with a lunch and a casual afternoon along with a welcome party. And we had a ton of fun. I really enjoyed getting to know all our team members, some returning again from last time, some new faces, some people that joined just a couple months ago. We did team building activities, we did excursions. Cebu's on the beach, so we did banana boating and snorkeling. We had a karaoke night. It was a blast. But like every event, there's always room for improvement. So let's take a look at some of the things that went wrong, some of the things that we could improve upon, some things you should look out for when you're running any event, especially a team retreat. Now, the top piece of feedback for things to improve that we saw on our feedback form is actually the food. In our team retreats, we basically give all our team members an all inclusive few days. So we take care of their flights, we take care of their hotel, we take care of their food, all their meals, their drinks, you name it. And when you do this, you're going to face some challenges because it's hard to cater for everybody's needs and wants and preferences, especially when you're trying to keep things as efficient as possible. We were at a resort and the resort did all the catering as well. So one of the things we had to look for is a resort that can do everything pretty well, has a good meeting room, has good rooms, is a good location, good service, and could feed us with some great cuisine as well as drinks. And it's a lot easier said than done. It's hard to find, especially when you're not in that country locally, a place that can check all the boxes. And of course everybody's going to deal with their particular budget, how much money they want to spend on this team retreat per head. So as much as you want to prioritize the important stuff, sometimes you're going to fall short. And in our case it was probably the food. We got some mixed reviews about the variety of the food as well as having more options for those who are like vegetarian versus those who don't eat certain foods. And the thing to keep in mind is the longer your team retreat, the more important this is because if your team retreat is a couple of days, it's not so hard for a place to have variety. But if you're going to be there for three, four, five days, you might face this challenge as we did. So next time around, what we're going to do is we're going to try to make sure that the food quality, the cuisine, the variety is. Is there at the place we choose. We might have to dig into the reviews of those places on TripAdvisor or look into maybe having some meals outside of the resort that can add a little variety. So that was a big learning point for us. You know, your food is part of the experience. You want to make sure that people are enjoying their meals, and we want to make sure that we do better next time around. The second thing that kind of didn't go so well was one of our activities, and that was a photo shoot. We hired a local photographer in the Philippines to come on over to our resort and take photos, take headshots, take team shots, apartment shots, some fun shots, maybe outdoors at the resort, just so that we can capture the moment, capture this great retreat with all our team members in person, as well as give us some photos to our team members that they can use in their own social profiles. In theory, this is a great idea. Now, this is one of those kind of activities that you're not in full control of, meaning that, you know, we ran activities with team members. Some team members led some activities themselves. I led my own activities. Nicole led some activities. And you feel like there's a sense of control, like, you know how this is gonna go. You can give clear instructions. You can control how well it goes to some extent, because you're doing it right. You can prepare your team members. You can help them out, you can give them the right materials. You can do everything you can to make it special. But when you outsource an activity like a photo shoot, like a photographer, you're basically at their mercy, and you're just hoping that they're gonna be great. Now, this photographer wasn't horrible. And in fact, when we saw the edited photos after the shoot a few days later, they look amazing. So the actual product that he produced was really good. But during the experience of the photo shoot or the photo shoots, I should say it wasn't that great. Let's just say the photographer lacked a little bit of initiative or didn't really give us much direction, so we didn't know what to do really. And maybe that's not his strong suit. And regardless of the fact that the photos came out great during the experience, the team members don't know. They haven't seen the photos yet being edited. And in the moment, their experience is not so wonderful. Almost like this is a little bit of a waste of time. And, you know, if you know anything about photo shoots, they take time. They're like two hours, three hours long, especially when you have many people Now, I don't regret the idea of a photo shoot. It was actually a lot of fun and the photos came out really well. But next time around, I'd probably have a video call with the photographer before hiring them or making the choice to go with them and hear from them, tell us how it's going to go. How do you like to run these photo shoots and hear what he or she's plan is when it comes to delivering the experience and not just the now. This might sound like I'm nitpicking, but we have a limited amount of time together at this team retreat. So every minute, every hour counts. And we want to make sure every experience is as good as it can be. Now for the third thing that we could have improved is maybe the schedule. So the schedule, we really try to have as much fun and work balance. So plenty of free time for the team members to explore the resort, enjoy the swimming pools, enjoy the beach, maybe go out and have some fun at the. And if you look at this schedule in terms of hours, it was probably pretty balanced. But I think we could have shifted some things around so that there is a balance every day. So maybe the first day was a little bit meeting room intensive. We could have moved one session to the next day and had more free time that day versus lots of free time another day. Of course, we're juggling, balancing excursions and good weather and all that stuff. So we wanted to make sure that we choose the right days to do the excursions and the fun activities. But what ended up happening is, you know, the weather was great all throughout, so maybe we should plan for balance regardless of weather. And this will allow people to be more recharged every day, especially maybe at the start of the retreat. The beginning of the retreat, because there's many people that are traveling 30 hours plus to get to the Philippines, they live pretty far, long layovers. So a bit more free time and the first, second and third day might have helped ease them into it. But our team retreat overall was fantastic. And let me highlight some of the things that we did really well and we would definitely double down on the next time around. Number one, activities that people can open up and be themselves. One of the activities that we did was we went out one night and did a karaoke night where the team got to sing songs and dance, enjoy some Refreshments and just have fun, right? With their team members singing along, smiling, being impressed by some people that really can belt out a tune, and those like myself who are just having fun regardless of how good they can sing, this builds bonds and relationships beyond work. In that moment, we all became friends, and that's amazing. Another great thing is our airport transfers. I know this sounds kind of nitty gritty, but we chose someplace that wasn't too far from the airport. Last time in Bali, the airport and our hotel was about two hours away. That's a long drive after some long flights. And the airport pickups weren't as efficient this time around. Our airport pickup was waiting for us right outside of the airport for every single person, every single group that came off flights. And it was only about a 25 minute drive. 20, 25 minutes, depending on what time of day. And they were at their accommodation ready to enjoy. The other thing that I really loved is we chose some really good activities to do as a team. To one, understand our customers better and two, come up with solutions for our customers to help them win. We had a theme throughout the whole retreat, which is when our customers win, we win. And in order to do that, we had to understand what our customers are feeling, thinking, worried about, what are their pain points? What are their struggles? What are they stressing out about when it comes to their business? And we created what's called an empathy map. And everybody on the team shared what they thought our customers are going through. And that allowed us to kind of open up and understand, wow, this is basically what our customers are going through every single day. How can we help them? And that kind of led us to the next activity. I got one more thing I want to share with you when it comes to what we did, right? When it comes to the team retreat. This episode is sponsored by Time Doctor. Measure and improve productivity wherever your people work. We've rolled out Time Doctor in our team and we're a few weeks in. The team has gotten used to using it and tracking what they're spending their time on. What I found was very interesting is how competitive people are becoming, sharing their numbers with each other. How productive are you versus my numbers? But it also allows us as management to help solve nagging problems. For example, in customer support, you've been trying to improve our first response time. We want to keep it under five minutes. Sometimes it creeps up to six and seven minutes. With Time doctor We know how much each customer service teammate is spending on each task and how they are implementing that task. This allows us to give them feedback and say, hey, this might be a better way to answer support tickets so that you can get back to people quicker and be mindful of how long you are taking to get back to a customer when you're trying to multitask. That's just one example. So far, so good. With Time Doctor I'll update you next week on how things are going on our team using Time Doctor. But don't take my word for it. Join me and over half a million happy customers and unlock the power of visibility, accountability and productivity with Time Doctor by starting a free trial today. Visit Time Doctor's website at www.timedoctor.com to get started. That's timedoctor.com for a free trial today.
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This time around, instead of Nicole and I doing everything in terms of the planning, the logistics and the implementation, we gave ownership to Romina, who is our executive assistant. She took ownership over this team retreat and yes, we helped her leading up to it and we took care of some tasks and we gave her input and made some decisions. But overall, all the heavy lifting leading up to the retreat, as well as at the retreat itself, Romina was the person that everybody looked to and I'm so glad we did this because it was far less stressful for Nicole and I. We weren't totally exhausted right after the retreat and Romina took care of it so well. She put her little flavor to it to put her own personality to it. And she reminded me that when you hire good people and you just tell them what you expect and let them figure it out, they'll surprise you. So delegate a lot of the logistics and the planning and implementation to an assistant is a huge, huge win. You should definitely do this because she has total ownership over this project. Less things will fall through the cracks. And of course we forgot a few small things or things didn't go perfectly as planned, but that would have happened regardless of who was doing it. And there weren't deal breakers. There weren't things that really would make or break the experience for the team. There you have it guys. I shared with you everything that went wrong and what went right with our team retreat. We are so excited for our next team retreat. We'll probably start planning it in a few weeks because all these great ideas are fresh in our mind. The experience is fresh in our mind. We know what to do not to do for the next time around. If you love this podcast, hit subscribe, hit follow on your favorite podcast app. By doing so, you get access to over 2,200 episodes in our archives. Thank you so much for doing that in advance. And if you love the podcast so so much, you can go the extra mile and share it on social. Go ahead and do that. Send them over to100nba.net so they can subscribe to the podcast. Before I go, I want to leave you with this. As much as I loved the fact that I got to know every single team member so well and bonded with them and and had memories and it was just a lot of fun, I'm even more ecstatic and happier that our actual team members got along with each other and got to know each other and built friendships and bonds. This helps your team work more efficiently, more productively, and of course, happily do what they need to do every single day. Thanks so much for listening. I'll check you in tomorrow's episode. Until then, take care.
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