ConvertKit Retreats: Why We Go & What We Do

Matt Ragland shows ConvertKit's twice-yearly retreat in Oceanside, where the fully remote team does support work and roadmap planning alongside surfing, paintball, and escape rooms. The real focus is communication: building trust through vulnerability, using I-statements, and getting comfortable with productive conflict.
Chapters
Hey, what's up everyone? This is Matt. Let me readjust. Light isn't what I thought, but hey, how you doing? It is Friday morning and I'm here in Oceanside, California, just outside of San Diego, about an hour. Let me show you where I am real quick before we kind of really get started. It's out here right on the ocean. It's the Pacific. Beautiful day. Getting ready to head out. We've had a great week. Week here at ConvertKit doing a— twice a year we get together, twice a year we get together and have a retreat. We're a fully remote company, and so having a time and a place that we can all get together and have some literal face time is really important for all of us. A handful of us live in Nashville, handful live in Boise, Idaho, and then scattered across the world. I mean, people from several different countries have made big trips to get here. Our spouses, our significant others make sacrifices to allow us to be here. And yeah, so we really, we really take advantage of the time. So I tell you why we do these besides just having the FaceTime together. There are some things that even for a remote company, even everything with video and we use Slack and Basecamp to get our work done and communicate with each other, Zoom calls, there's still something special about being face-to-face in person with someone. And that's what we get to take advantage of. It's also a great time where we get to really talk about where we're going as a company and what, what our vision is like as employees. We get to hear a lot from the directors, from Nathan, the founder, and just We all have time together, which when even if you're working, when you're working remote especially, when you're working with any people, you don't always have like those in-between moments that can be really powerful and just going to give you more context for everyone as people. And literally living together for a week will fill in a lot of that context for how we understand each other as people. And so that's That's why we, we get together again twice a year, and it's, it's some of the most special time each year for me. Okay, what do we do? What do we do during this time? We get together, obviously, and we do a lot of work. We have some fun. I'll talk about that in a second, but we are still spending time responding to the day-to-day support questions of customers. We hash out some bigger features, or we look at our product roadmap and discussed that quite vigorously as a team, and you know, everyone has a voice here, and I think that's one of the best things about ConvertKit is that I feel like everyone's voice is heard, and that's, that's a really important part. We also, we also do have some fun. So on Monday, half the company got massages, myself and the other half of the company, and were massaged by paintballs. And so a bunch of us, I think, along with some of our local customers, got together and went and played paintball, and a bunch of people got massages here at the house. That was a lot of fun. And then on Wednesday, half of us went to surfing lessons. So got to surf for the first time down there, Surf Ride, Surf Rider surf shop. Did the lessons. They They were fantastic, stood up on the board several times, and that was, that was a lot of fun. There's something really cool about feeling yourself glide, glide along the water. And so we do have some fun. A bunch of people went to an escape room, went on a hike, and we all went to dinner last night at name of a restaurant that I can't pronounce over in Del Mar. So we just got on the 5 and went south. And then got on the 101 and headed to this restaurant. And it was great. So, you have to let me know how I did with that. Where? This is, again, we do these all over the place. This one is in Oceanside, California. And last one was in— hey, Alexis! Last one was in Boise, just outside of Boise in McCall. And that was a lot of fun. Also, 'cause we're at the beach, we've been at the mountains, we'll probably go back to the mountains next. And so we get to, and the biggest thing is just being together. And it's beautiful and wonderful to be in such a pretty place that's very, like, I draw a lot of energy and inspiration from the landscape around me. So that always helps. But really the biggest thing is being together. And there's just no substitute for that. One of the things that has come up a few times that some of us has said is that we're committed to being a remote company. And everyone loves that flexibility, but this is the kind of company that you would move somewhere for. That's how I feel. And so it is kind of funny that we just all love spending time together. One other thing that I want to bring up in terms of a big takeaway that I have is that we talked a lot about team communication on this retreat. And it's really important. It's important whatever kind of relationship you're in. If you're in a working relationship with someone, you're in a romantic or family family or just friendship with someone, the way that you communicate with them is incredibly important and powerful. And we talked about that a lot. It's something that you have to be really mindful of as a remote company, but no matter what kind of relationship you're in, it's important. Like, I came away thinking of ways that I could communicate with my wife better, that I could communicate with my siblings, my parents better. The two biggest things on that, when you're giving feedback to someone, so let's say you have the the courage, you have the trust, you have the vulnerability with someone that you go to them when there is a conflict. And I think we all have to be more comfortable with conflict. Okay? Because when you know that the person that you're in conflict with, when you know there's that baseline of trust there, then you can go into conflict because you know it's not going to change anything. All right? And it'll probably help strengthen that trust and resolve and vulnerability that you have with each other. And when you go into that, instead of saying like, well, when you said this, it's a, it's an attacking point of view, right? And it puts the other person on the defensive. They're like, whoa, I did not mean that. I can think of several times that, you know, I've done that. I've said that. Instead of that, go to it and say, I heard this, it made me feel this way, and A lot of times a person will be like, "Oh, that wasn't my intention at all. I'm sorry." 99% of the time, that's how those conversations go. And even if there's still a, "Well, it did make me feel that way," or, "That's what I heard," you can, with enough time, you can kind of work through that. But instead of— again, try it next time you're in conflict. Of going into the conversation instead of saying like, "Well, you said this," or "You did that," you know, instead of like pointing the finger, you know, just like, "Hey, this is how I felt. This is what I heard. This is the way that I understood." So instead of it being you-facing, turn it around into I-facing. Again, that takes a lot of trust. That takes a lot of vulnerability to be able to do that. It takes a relationship, but that's what we're all in even though, you know, we work together. We are building, we want to build a culture, a community of trust and vulnerability and long-term relationships for the work that we're doing. Okay, we got to finish cleaning up. We got to get out of here and get to the airport. Long day of flights ahead. Shout out to Danny Stewart, flying buddy for today, and can't wait to get home, see my wife, little guy, little son, my dog. It's going to be, going to be a good day. So safe travels to everyone. Hope you're all having a great day, great weekend, and I'll see you tomorrow. Take care. Bye.
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