When we started doing Close.io team retreats, there wasn’t much planning involved.
For the first three years, our entire company consisted of six people.
We’d travel to another city—all six of us—and get some work done. For the most part, we carried on as if it was any other week.
But as we’ve grown, things have gotten more complicated. We can’t just cram a bunch of people into a house and work side-by-side anymore. Today, we’re a team of 27—and we’re in 11 different countries.
To account for a larger team, we needed to get organized. We needed a system. And while it’s not perfect yet, we get better and better with each retreat. So let’s talk about how we design our remote team retreats so that we get the most out of our time together.
Want to organize your next team retreat like we do? Download our team retreat planning templates!
Retreats aren’t supposed to be typical work weeks
I often tell the team that they should expect to get less work done on retreats—and that’s okay.
There are two priorities at retreats, especially for remote teams:
- Create alignment. Get everybody on the same page. When your team works all over the globe, there’s always a chance for misalignment. This is your opportunity to rally everyone around a common goal, provide context, outline your plans for the future, and identify what’s truly important to you and the company.
- Build relationships. Thicken the social fabric. Spend quality time together. Get to know each other. Working side-by-side encourages cross-functional communication and understanding. Don’t waste an opportunity to develop and strengthen your team culture.
This may seem like a small thing, but meals are really important at Close.io retreats. They’re rare bonding opportunities for people who sometimes live thousands of miles apart.
We always book a hotel that has plenty of breakfast and coffee options nearby. We schedule one group breakfast—with no more than 3–4 people per group—but for the most part, we let everyone start their day however they prefer to do so. The early risers grab food together, while others head out for a quick, last-minute coffee before the work day begins.
Unlike breakfast, lunches are scheduled throughout the week. We typically find a few good restaurants around the coworking space, and order meals in advance. One week before the retreat, we send out a spreadsheet with links to each day’s menu.
We eat lunch in small groups. If you’re an engineer, you’ll eat with people from marketing, support, and sales, and we rotate groups every day. We do this because, when we’re all together, we tend to hang out with the people we know best, the people we interact with most often. So we try to counteract that as much as possible.
We typically have two big team dinners—one on the first night, one on the last night. We schedule small group dinners the rest of the week. At the small group dinners, we like to give everyone something to discuss, as a way to kickstart conversations.
It may seem corny to dictate a conversation, but we learn incredible things about each other at these dinners. Recently, we encouraged everyone to share something about their parents. I’ve worked with some of these people for five or six years, and the stories they told that night really helped me connect with them on a new level. I understand them so much better now. It was a really inspiring conversation.
Since we don’t share office space throughout the year, and we don’t go out for drinks after work, this is our opportunity to cram a whole bunch of bonding into a short amount of time.
At the end of the retreat, after the last dinner, we all go out for the night. This is a completely mandatory event. You don’t have to drink or dance, but you do have to hang out for a while, spend time with us, invest in your team. We’re all getting on flights the next day, and we won’t be together for six months. This is our last chance to take advantage of our limited time together.
Obviously, we spend a lot of time thinking about this stuff. We don’t leave anything up to chance. Meals are some of the most important moments of the entire retreat. When we break bread, we come up with our best ideas and solutions. We generate meaningful discussions that carry into the following weeks. We grow stronger as a team.
Choose a motto
You need to summarize the focus of the retreat, so that everyone is aligned for the week.
At our most recent retreat in Dublin, the motto was: Getting back in touch with our core customers.
I’d noticed that, for a number of reasons, there was a growing distance between us and our end-users—the salespeople who actually use our product every day. As a result, that distance created some small problems that I wanted to correct immediately. I chose this motto so that we could get aligned on how to solve these problems. That entire week, we talked about the ways we could make our product, customers, and company more successful by focusing specifically on our end-users. By the time we left Dublin, we knew exactly what we needed to do to make that happen.
Invite your customers
We’re huge proponents of customer intimacy at Close.io. The closer you are to your customers, the more you understand them, and the more value you create for them. That’s why we like to invite customers to participate in our team retreats.
We’ll often visit with local customers during that week. We like to bring people who don’t usually meet with customers in-person. It’s really inspiring to walk into a customer’s office and see people actually using the software you’ve developed. It’s something you can’t really replicate in a dashboard.
Sometimes we’ll also invite customers to give talks or conduct Q&A sessions at the retreat. If there aren’t any customers in the city we’re visiting, we host a video call with a customer in the same time zone. These are great opportunities to learn from the people who use our software most often. And it’s an opportunity for them to provide feedback, and ask about specific features and workflows.
Record and stream everything
It’s always a good idea to revisit a retreat in the months that follow. That week is pretty intense, so it’s difficult to absorb every single thing that we discussed. That’s why we try to record everything—team meetings, customer interviews, brainstorming and planning sessions. We keep everything—all the photos, videos, presentations, and documents—in a shared Dropbox folder so we can access them whenever we want.
As our team grows, it’s hard to get every person to a retreat. No matter how mindful we are about schedules and locations, there’s always one or two people who can’t attend. When this happens, we try to set up video streams for the big meetings, presentations, and interviews. A couple retreats ago, four people couldn’t join us, so we created a satellite retreat during the same week. We found a city they could all easily travel to, paid for their hotel rooms, and they joined as many live sessions as the time zone difference would allow.
What does the retreat schedule look like?
Every day has one—and only one—big meeting. There’s a lot of other stuff that fills up our day: customer visits, internal meetings, one-on-ones, etc. So we don’t want to bog people down with unnecessary team meetings. In truth, we only really have three hours a day to do normal work, so we have to be careful about schedules. There just aren’t enough hours in the day.
- Day 1: We have a kickoff meeting, where I welcome everyone, set expectations, talk about the retreat’s motto, guide them through logistics for the week, and look back at the last team retreat. In that review, I summarize goals, what we discussed, the decisions we made, and what’s happened since. This sets the stage for the week ahead.
- Day 2: We focus on company values and culture. We have another member of the team lead a session on our core values, and we have others share stories of how we live those values. We also evaluate whether these values are still relevant, and take time to talk through those ideas.
- Day 3: We have a product roadmap meeting. The product team talks about what they’re working on, and they usually share a demo or plans for future product developments.
- Day 4: We focus on the week’s motto. This is a pretty lively conversation, where people bring a lot of great ideas to the table.
- Day 5: We reaffirm the vision for the company. What are our goals for the next six months? What are we trying to accomplish? Why is this important? How can we all help the company succeed? I also lead one final Q&A session. Throughout the week, people send me questions, and I curate that list and address anything we haven’t discussed throughout the week.
Depending on the schedule, we also like to do a sales workshop. This is especially useful for new hires and anyone not on the sales team. We want everyone in the company to have a high sales IQ, so we try to carve out some time for a quick tutorial on the ABCs of selling and our sales philosophy.
The retreat is also a good opportunity to have one-on-ones, whether they’re quarterly check-ins or performance reviews. To this day, no matter how much we grow, I try to have a one-on-one with every single person in the company, just to see how they’re doing and what I can do to help.
Survey the team regularly
Check in once a day to see how the retreat is going for everyone. If they’re upset about something, or they want to discuss a specific issue, it’s good to find out sooner, rather than later.
Early on, we surveyed the team a couple weeks after the retreat, and they brought up some really great questions that we absolutely could have addressed while we were all together. It’s important to iterate throughout the week and get feedback, so that you provide tons of value to your entire team.
Take lots of photos and videos
For the last two retreats, we’ve had someone on the team create a slideshow that we shared at the last meeting of the retreat. It’s a cool way to remember all the fun stuff that happened during an insanely busy week. We also add photos and videos to our recruiting page, so that candidates get a sense for how we all work together. It’s a great recruiting tool for us.
Check out this video that Alberto put together after our most recent team retreat in Dublin, Ireland:
Plus, we all get retreat withdrawals, so it’s therapeutic to share photos and videos when we're back home. It helps to look back on all the positives from that week. Those good vibes carry over, and really energize us for the next couple of months. It’s a hugely inspirational time for our company.
Sweat the details
We’re lucky to have Mary, our queen of culture, oversee nearly every aspect of that week. In fact, she does most of the heavy lifting. Without her, our retreats wouldn’t be nearly as amazing as they are.
Why is she so great? Because she sweats the details. She manages our itineraries and flights, hotel and restaurant accommodations, transportation within the city, and generally makes sure everyone’s taken care of. She even leads a discussion or two during the retreat. Seriously, she’s a rockstar. If you don’t have a detail-oriented person on your team, who you trust implicitly to own the entire retreat, go out and find one immediately. To pull this off, you need a Mary.
Retreats are a huge part of our culture
If you’re a remote team, retreats are your best opportunity to get aligned, set the course for the next six months, and strengthen your team culture. Yes, the planning can get complicated, but the time and energy you put into planning these retreats can absolutely make you a stronger, closer, and more motivated team. And that’s all that really matters.
Want to plan your next team retreat like Close.io? Download our retreat planning templates!