The REWORK podcast

A podcast about a better way to work and run your business. We bring you stories and unconventional wisdom from Basecamp’s co-founders and other business owners.

EPISODE 0043

How Buffer Meets Up

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Even remote companies need actual face time every once in a while. That’s why Basecamp holds companywide, weeklong meet-ups in Chicago twice a year. Fellow remote tech company Buffer has 85 employees across the globe that get together once a year for an annual retreat, and they’ve visited countries from South Africa to Iceland. On this episode, Carolyn Kopprasch of Buffer talks about the kind of work that gets done during this time, helping introverts manage energy during an intense week, and her favorite parts of Retreat.


The Full Transcript:

Jason: [00:00:00] All right. It’s award time. Peer awards, and the first one is going to be presented by Michael.

Michael: [00:00:09] Is this thing on, Shaun? Oh, sorry. was just testing it and giving you some levels.

[00:00:15] Broken By Design by Clip Art plays.

Shaun: [00:00:19] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Shaun Hildner.

Wailin: [00:00:23] And I’m Wailin Wong. In May, we at Basecamp held our semiannual meetup. Twice a year in North American fall and spring, we fly everyone to the Chicago office for a week of face-time. Basecamp is a remote company with people based in places like Rio and Hong Kong, so the meetups are important for getting to know new employees and making connections with colleagues that hopefully carry through to the remote work we do together the rest of the year.

Shaun: [00:00:49] We’ve been meeting up like this for many years now and mostly in the same format. Monday is sort of this state of the company talk. Tuesday, we have an all-company dinner and Wednesday is when we recognize our coworkers with a little award ceremony. But more importantly on Wednesday we play Dungeons & Dragons and eat pizza that night. In between all this planned stuff, it’s basically free time for small teams to get together or just to hang out and play board games. It’s pretty unstructured.

Wailin: [00:01:16] I thought it would be useful to talk to someone at a different remote tech company about how they do their meetups. Today on the show we have Carolyn Kopprasch from Buffer. They do one big gathering every year that they call a retreat and they do things a little differently from Basecamp.

[00:01:31] Carolyn had some advice that’s useful not just for a remote company meetups, but for any kind of all hands gathering. So here is my conversation with Carolyn.

Carolyn: [00:01:44] I’m Carolyn Kopprasch. I am Chief of Special Projects at Buffer. We’re a software company. We build products for companies to help build their brand and what we primarily focus on is social media. So we help people publish to Twitter and Instagram and Facebook and things like that.

Wailin: [00:02:01] Does Buffer have an official headquarters?

Carolyn: [00:02:04] We don’t anymore. We had one in San Francisco for a while, but it was extremely expensive, as anyone who has ever rented space in San Francisco can attest. We had the experience of not a lot of people going to the office and so it was a little bit of a waste and we are remote first and we believe that very firmly. So, we decided to do away with it.

Wailin: [00:02:25] So how many employees does Buffer have?

Carolyn: [00:02:29] I think right now we’re at about 85.

Wailin: [00:02:31] And how long have you been doing your Buffer retreats?

Carolyn: [00:02:34] Oh, good one. We’ve been doing retreats since the beginning. When we started it, I don’t think we knew that it was going to be quite such a tradition, but we were just a group of people spread out all over and we realized that we needed to get together.

[00:02:48] We first met in San Francisco, that was our first one and we immediately saw the benefits of that and we had so much fun. And so it became a thing that we did after that first one. So yeah, it’s kind of been a part of our DNA since the beginning.

Wailin: [00:03:02] And has the location moved around or is it always in San Francisco?

Carolyn: [00:03:07] It always moves around. We try to alternate between a North American location, a European location, and somewhere in sort of Asia/APAC region. So we’ve had retreats in Hawaii and New York and Thailand and South Africa and Madrid. And we have a dedicated people team and they do a lot more than just planned retreat. But there’s one teammate in particular whose whole job for at least the three to four months before retreat is planning. And then it’s a huge percentage of her job for the rest of the year. And she often does a scouting trip in advance. So she will go to the location a couple of months in advance and go to the hotel and walk into the conference room and test the Wi-Fi, and check out local coffee shops and talk face to face with the hotel manager and whatever. So that’s a really, really big help in planning.

Wailin: [00:03:58] Have you found that like certain kinds of venues work best for like this kind of a retreat and a group of your size?

Carolyn: [00:04:07] Yeah. It depends on who you ask.

Wailin: [00:04:12] I’m sure. 85 people in company, yeah.

Carolyn: [00:04:12] Right. There’s probably an island cohort and a city cohort. The biggest thing that we’ve learned that has been really consistent in terms of this works and this doesn’t, is temperature and climate / also relevant is time of year. So when you’re coming to a warm place or at least a warmish place, it’s more relaxed. There’s less stress about traveling, people get sick less often. There’s just kind of this general better experience when it’s someplace warm. I mean, not to say that we haven’t had wonderful experiences in some of the colder locations and it’s actually still a dream of ours to do like a ski trip. So maybe some sort of very cold location. But, at least for the big companywide trip, warmth is the key.

Wailin: [00:05:09] Does the team that plans it, do they take employee suggestions or is it more of like an executive decision?

Carolyn: [00:05:16] We used to just kind of like pick a couple places and then all vote. And that used to work well when we were like 15, 20, 25 people because it was always easy enough to find a place that could accommodate us. Now that we’re 85, we are a little bit more limited in terms of the places we can go and the types of hotels that can accommodate. What we ended up doing, usually, is that the people team and the planning team will choose like three or four or five locations that might work and really, really vet them and figure out, okay, really what’s the budget here? And start negotiating with hotels and map out the travel costs and all that and get it down like roughly three choices. And then the whole company votes on that. And if you think that you don’t have company participation in surveys, get them to vote on where the next retreat is because that’s usually 100% participation. Everyone is excited about that poll.

Wailin: [00:06:13] Oh, I’m sure everyone’s got feelings, too.

Carolyn: [00:06:16] Many. All the feelings. Yeah.

Wailin: [00:06:20] So after that very first one when you’re like, oh, this is great, we should do this all the time. Was that when you kind of put in more of a formal structure to how those retreats would go? Or did that structure evolve over time?

Carolyn: [00:06:34] It definitely evolved over time. We were so small at first, like when we did our first retreat, I think we were eight, nine people. So it was very informal. There was certainly no one on the team dedicated to planning and executing. It was just kind of all of us pulling together. Someone handled hotels and someone handled… or actually at that in the early days, we used to do AirBnBs. Someone would handle booking a restaurant for us for dinner.

[00:07:03] And at a certain point we started trying to achieve a very specific thing at retreats. So probably in the mid years, we would set this big ambitious goal and then all work toward it. And as the team got bigger and bigger and as we reduced the frequency of retreats also, which used to be two to three times a year and now they’re once a year. We decided to just have it be a time of reflection and looking forward and kind of just being together and working together and not necessarily trying to have this big ambitious goal for the week. And so that’s when we ended up with a pretty traditional schedule where we do a couple of days of companywide focus and a couple of days of team focus and like a little bit of playtime.

Wailin: [00:07:49] Before, when you had a big goal that you wanted to accomplish at the end of the all company retreat, would that be like launching a new product or perfecting something, like finishing something that everyone had been working on? Something like that?

Carolyn: [00:08:03] Yeah, exactly. The example of our Thailand retreat was that we launched an entirely new product. Our engineers just cranked on that all week and everyone surrounding them was just kind of trying to support that effort. And giving advice and all that. And that was a really cool experience and something that I recommend doing probably when you’re very small. But the thing that we realized is that we flew to Thailand and saw the inside of a conference room the whole time. Like we didn’t really do much other than work. And so when we all flew home, we were like, we could have probably just done that in San Francisco. So that was kind of, that was like a really cool bonding moment. But we also had this moment of thinking, okay, we probably don’t need to do that on retreat. We can do that at other times that we can like really push on a goal other times in the year and not necessarily make retreat about that.

Wailin: [00:09:01] How come you scaled back from two to three times a year to once a year? Was it just a question of costs and logistics as the company grew?

Carolyn: [00:09:10] Yeah, it was partially cost. And it was partially… we introduced the concept of a mini retreat or an onsite, where smaller groups meet up. So with the entire company, it’s obviously really special and wonderful because you get to see everyone, but it can be a little hard to really get a lot accomplished with your individual teams.

[00:09:34] So, at this point now we do one annual companywide retreat and then we also do a team-wide meetup at some point during the year, usually roughly half a year after each retreat. So, you can kind of break up the time apart and those smaller ones are a lot more focused and very heads down and just mostly trying to achieve something or really leap frog a challenge. Whereas the companywide ones are more about just connecting and looking toward the future.

Wailin: [00:10:03] So then on Twitter, when you had posted a few, like kind of a thread of tweets about how you do your retreats, you had mentioned that on Mondays you have team-wide sessions that are more focused on long-term planning and vision stuff. Tuesday and Wednesdays are breakout sessions. Thursday’s a day off. And then Friday is kind of a lighter day of work. Can you talk a little bit about, kind of the wisdom that goes into structuring each day like that, kind of keeping into account… What I think about is like how tired I already feel by like Tuesday afternoon.

Carolyn: [00:10:39] Yeah. Yeah.

Wailin: [00:10:41] Can you talk a little bit about kind of like making sure that people have time to work but not kind of exhausting them too much?

Carolyn: [00:10:46] Yeah. So that’s a really good point. Managing energy is such a hard thing to do as a human anyway. And then you have this unique, highly intense, exciting, exhausting week. And managing energy becomes like the most important thing you can do as a company and probably as an individual. So we take that very, very much into consideration when we plan the week. So yeah, Monday, is kind of this high energy excited day. Everyone’s hopefully slept a little bit and is arriving sort of bright eyed and bushy tailed. And so we do a big all company day that day.

[00:11:26] Joel, our CEO, gives a sort of like a big reflection on the previous year and we celebrate goals we achieved and we look forward to the future and talk about our vision and stuff like that. After a full day of all being in the same room, it can be a little bit hard to walk back into that same room and do a second day.

[00:11:48] So what we found is that Tuesday and Wednesday we do kind of breakouts. So the engineering team gets together and the entire product team gets together and the design team, and the marketing team and they do kind of a mini, just like a focus day with their own team.

[00:12:03] Wednesday night, which is sort of like the halfway point or just past the halfway point, we do a big celebratory team dinner. We do a couple of things to kind of make that special. Like at some point in the night, every other person stands up and switches to another seat so that you can sit next to, not only two people but, but four people throughout the night. And then we have Thursday as a day off. But it’s like usually we explore the city a little bit. That was the lesson that we learned in Thailand when we flew home and were like we never left the AirBnB.

[00:12:37] And then Friday is all company day again, but it’s a little bit lighter. Like we do team jeopardy and that gets very competitive. And you know, we also do things like all hand support on that day. So the whole company does all hand support for two hours and tries to get the inbox down a little bit.

[00:12:52] And we end on a somewhat serious note, which is we do a gratitude session and this is probably, it might not be an exaggeration to say it’s one of my favorite days of the year. It’s certainly my favorite moment of retreat and, it’s a really, really special thing where we all sort of just pass the mic around and talk about things that we appreciate about individual people or the company culture or just anything that comes to mind. And then people start to filter out either Saturday or Sunday, depending on how quickly they need to get home.

Wailin: [00:13:29] And then you do a companywide day off on the Monday afterwards, right. Just to give everyone that extra time to recover.

Carolyn: [00:13:36] Yes, that’s a new addition and it’s wonderful. It’s just one of the best parts. Because otherwise you get back and you’re tired and your family feels like they haven’t seen you. And especially if you travel on that Sunday and if you have far to go, like you can feel like by the end of the week after retreat, you can feel like you’ve been going nonstop for three weeks. So that Monday is a good reset day. People can do laundry and kind of relax and reconnect with their routines. And that is a blessed gift. So that’s now one of our staples of how we do retreats.

Wailin: [00:14:16] Do you have a way, formal or otherwise, maybe more informal of capturing and organizing the ideas that come out of that retreat, especially if it’s… a lot of the work that’s done is forward looking and planning. Do you have a way of capturing all that so that, there’s accountability and understanding of kind of where you go after you’ve settled back into your normal work routine?

Carolyn: [00:14:39] That’s a great question. We don’t, actually, we probably should. It’s sort of expected that the individual team leads will take the lead on that. We also tend to take notes transparently. So as a company that values transparency, we often use a tool like Dropbox Paper so that anyone can access them anyway. So that’s a little bit of natural accountability. But we also, for the big session, we record it. We always have that running live for the people who are at home and we have it on video so that anyone can rewatch it.

Wailin: [00:15:15] I wanted to spend some time talking about energy management and then also emotional management. How do you accommodate introverts? And even extroverts who aren’t used to that much face to face time. Because I feel like I’m one of the most extroverted people at Basecamp. And then again usually by Tuesday, I’m like, I’m so tired.

Carolyn: [00:15:35] Yes.

Wailin: [00:15:36] And I don’t even have to travel. I live here.

Carolyn: [00:15:39] Yes, yes, yes. So that’s such a good question and it does depend a little bit on where you go and what you’re trying to accomplish. But we have a bunch of things that we do to try to help with that because it’s just a reality, right? Like it’s just going to be a factor that people are going to get exhausted and it’s kind of, it’s just such an intense and different week.

[00:16:01] Well the first thing is you just have to be prepared that like when 85 people take at least 85 plane rides, if not more, for layovers, like people are going to bring every illness from all over the world. So like retreat flu is such a thing. And so like we always tell people the week before, as much as you can, try to exercise, eat, eat well, sleep like set yourself up for the best possible immune system that you can.

[00:16:30] But outside of actual sickness, we try to manage this a couple of ways. One of my favorite things that we did this year was we actually delayed our start time by an hour. So we used to start at like 8:00 or 8:30. And then we went to 9:00 and this year we did 9:30. And that was heavenly. It allows people exercise or sleep in, or just have some introvert time in the morning.

[00:16:57] Some other things we do are just making it very acceptable to take introvert time. So we scheduled breaks very intentionally and we try to model the behavior of it’s totally okay to spend this 15 minutes like taking a walk or playing Sudoku on your phone or like whatever it is you do to have your brain not be in total full on mode the whole day. And to kind of give people a chance to reset and rest a little bit.

[00:17:30] And the one nice thing about this one in particular is that our CEO Joel is definitely… he identifies as an introvert. So he does this a lot and he’s pretty good about just going off and doing it and saying like, okay, that was a great conversation. I’m going to go take five minutes by myself. So Joel kind of models that behavior and then the rest of the company feels like they can do it too. And the only thing about that that’s kind of tricky is that you have to actually stay on schedule in order for the breaks to happen. So that’s something we’ve learned in 10 retreats also is, it’s not just about scheduling the breaks, it’s about being pretty disciplined about ending on time so that people can actually take those breaks.

Wailin: [00:18:08] Do you do anything special for, employees for whom it’s their very first retreat?

Carolyn: [00:18:15] Yes, we do. Good question. I often lack a little bit of empathy here because I’ve been on the team so long and I’ve been at every single retreat, so I just forget how hard it is to walk into that room on the first day. Like you know your teammates pretty well and you are connected to them and you feel like you’re a member of the team. But changing from a remote teammate to walking into a room with like 80 people is just… it just can be incredibly intimidating.

[00:18:48] It can also be hard to just like walk up to a group and say, what’s everybody doing for dinner? Like, we have a buddy system where every first-time retreater gets paired up with someone who’s kind of a vet. They kind of just look out for them a little bit. So, make sure that they had a chance to take a break and they feel like they have all their questions answered.

[00:19:10] And that can range from things like, okay, what do people normally wear on the Wednesday dinner up to like how should I approach this idea that I’m having? Like, who are the right people to talk to about that or whatever. And then on retreat it’s expected that that person will just look out for the new team member a little bit, like, make sure they have dinner plans or that they are taking the day off, the night off on purpose. So it doesn’t sort of end up being accidental introvert night. People are of course welcome to do that, but we want it to be by design and not because they didn’t feel like they could walk up to a group and join a dinner.

Wailin: [00:19:49] Do you provide support to employees who do not have as much experience traveling internationally?

Carolyn: [00:19:56] We do now. That was another lesson that we learned through time. So, I always think of the… of one of our earliest retreats. We went to South Africa pretty early and one of our American teammates had… I don’t think that he had ever been out of the country. And there’s one example from later where I think there was a teammate who maybe had never been on a plane before. That’s a good example of like why you need diversity of experience and background in a team. Because when it’s people who are all sort of of the same life background, like people who are of the same age and have had the same opportunities, we all just assume that this experience is going to be really comfortable for people. And then you realize that it is not.

[00:20:45] Now we really try to get ahead of it and say like people ask questions about vaccinations and how do get visas and how to update their passports or get passports. And those are all things that we try to help with now. And that was all lessons learned.

Wailin: [00:21:01] What do you personally get out of retreat that you find really special and different from, you know, working remotely the rest of the year?

Carolyn: [00:21:07] I mean, the most obvious thing is that it’s sort of a condensed kitchen serendipity that co-located teams have. I feel like when I worked in an office you would run into people getting coffee or having lunch in the kitchen and you would just have conversations that aren’t scheduled. And those are so hard to make happen remotely. We have all kinds of tricks for it and they work to varying degrees, but it’s just not the same as having five minutes really in person, next to a person who you can say, what are you working on or what’s going on in your life? Or even like how was your trip on your vacation? And that conversation turns into something where someone says, oh, actually I met so and so, and here’s an idea I had while I was traveling or whatever.

[00:21:55] Like those things are just, they happen in Slack and they happen informally, but it’s just not the same. So that kind of human connection and the serendipity that comes out of that is so, so valuable. And usually the couple of weeks after a treat, there’s all kinds of connections firing that that didn’t exist before. So an engineer and a person on that customer advocacy team realized that they’re approaching the same challenge from a different direction and they work together on it. And two people, two team leads from totally different areas of the company realize that they’re struggling with the same challenge. That sort of human magic that happens is really wonderful.

[00:22:36] Broken By Design by Clip Art plays.

Wailin: [00:22:38] Rework is produced by Shaun Hildner, and me, Wailin Wong. Our theme music is Broken By Design by Clip Art. Special thanks to Deena Prichep for her help with this episode.

Shaun: [00:22:47] You can find Carolyn on Twitter @CaroKopp, that’s C-A-R-O-K-O-P-P. If you want to learn more about Buffer’s, company culture, they blog about it all the time at Open.Buffer.com Carolyn mentioned that smaller teams at Buffer do their own meetups during the year and there’s a blog post about how they run those events. We’ll link to that in the show notes, which you can find at rework.fm.

Wailin: [00:23:21] I always miss that night too.

Shaun: [00:23:22] I wrote you into…

Wailin: [00:23:25] You did?

Shaun: [00:23:25] Yeah, yeah. So they discovered they’re like in this, haunted, massive—

Wailin: [00:23:28] Mansion?

Shaun: [00:23:29] —mass of ships.

Wailin: [00:23:30] Oh! Ooh.

Shaun: [00:23:30] You know, going from hull to hull and scrawled on one of the walls is Meghan Markle Sparkle was here.

Wailin: [00:23:37] Lady Mary Markle Sparkle.

Shaun: [00:23:38] Mary, that’s right.

Wailin: [00:23:39] Lady Mary Markle Sparkle. Oh, Man. Well, thank you for including me.

Shaun: [00:23:43] Anytime.

Wailin: [00:23:43] Am I a spooky ghost? Can I come back as a spooky ghost.

Shaun: [00:23:46] Uh-huh.

Wailin: [00:23:47] Now I’ll be Lady Mary (Moaning Myrtle) Sparkle Markle.