How we make our team retreats meaningful

As an all-remote team, we know that we need to prioritize in-person time together. At the end of every quarter, we rate our happiness at work, trust, relationships, communication, and teamwork on a scale of 1-10. When we don’t see each other in person, there is a trend in our relationship score: It never seems to be higher than 8 or 9. But since the pandemic, we’ve noticed a big increase in that score during the quarters that we’ve prioritized seeing each other in person.

Since we discovered the link between in-person time and higher relationship scores, we aim to get the whole team together at least twice a year, and we are proactive about blocking that time on our calendars.?

The first time we saw each other this year was, of course, when the team surprised me in Houston in May. And the second time was . . . last weekend! The team and some of their families came to my home in Michigan. We spent five days together and had a pre-holiday celebration, complete with matching pajamas, holiday movies, board games, and lots and lots of delicious food. It wasn’t the fanciest thing we’ve ever done, and it wasn’t the farthest we’ve ever traveled, but it was the most calm, cozy, and restorative retreat I think we’ve had as a team. It really felt unplugged, and I just felt like myself. I didn’t feel like I had to put on a show or follow a strict agenda. And I think that’s what made it so valuable. That we could have time together to just . . . be.

Our in-person time together hasn’t always looked or felt like that. It used to be that retreats were the only time we did real strategy work together. We would cram all of these intense, big-picture conversations into a short period of time, and instead of leaving our trips feeling relaxed and connected, we’d feel tired and depleted. Even worse, we would miss out on spending quality, unstructured time together.

Now, our retreats are focused on connection, and we tackle strategy conversations on Zoom on an ongoing basis so nothing piles up. If work topics come up during a retreat, it's not that we don't talk about them; it's that we let topics surface organically. Instead of having retreat agendas filled with work topics, we have itineraries of activities focused on strengthening our relationships.

I understand that we might need a business purpose to justify a retreat, especially considering that it’s an expense. But what if the purpose is to connect and learn more about one another? To let conversations naturally evolve, and not to be so rigid and structured? The more connected we are, the better work we will do together.

I get asked a lot about how to plan a meaningful retreat, so I thought I’d share some of our best practices when it comes to planning our time together:?

• Proactively save and budget for our retreats: This year, we added sinking funds to our budget. At the end of each quarter, if we don’t use all of the funds allotted for business expenses, we reallocate the extra to sinking funds to get ahead on expenses that we know we will have in the future. In addition to our retreats, the categories that fall into our sinking funds include our team’s computer and office upgrade budgets and food and self-care budgets (we talked more about these in a recent post ). This allows us to have the money we need set aside before we even start planning our retreats, and it gives us a budget to stick to. The team can choose to have a smaller retreat with the budget we have available or let the funds sit and grow longer for a more extravagant retreat.
• Determine owners of logistics and planning: Not everyone loves planning, so we give each person the option of being involved in the planning process or just showing up to enjoy (and no judgment!). For example, I love making everyone feel special and coming up with the ideas for the sweet and personal touches. Monique is the queen of the details, so she creates things like the itinerary and the budget to keep track of all of our expenses during the trip.
• Understand how many times in-person connection needs to happen to keep your culture and relationships strong: We try to get the whole team in one place at least twice per year because that’s what we’ve learned works best for us, but every team is different. I think it’s impactful to have a conversation with your team and understand how connected or disconnected those on your team may be feeling. The goal with retreats is to be proactive about planning them so that you can avoid feeling disconnected. A really impactful question you can ask: “How would you rate our trust and connection on a scale of 1-10?” Depending on what the answers are, it may be an indicator that it’s time for a retreat.
• Extend invites to families and significant others: We don’t do this every time, but occasionally, we will include family members in our retreats. It makes it really special! It’s a great way to get to know each other and the important people in each of our lives. At our retreat in Michigan, we had a couple of spouses and Monique’s son, baby Atlas, join us. One time, we even invited our parents to a retreat—it was so, so special!
• Understanding that there may not always be “good” time: Sometimes, life is just busy, and we can’t take time away to unplug. The trip in May was a great example of that. We hadn’t seen each other in so long, and the team knew that I was so busy that it would be a long time before I could slow down and come to a retreat. So instead, they came to me. Though we had to work pretty much the whole time, we still made time for connection, and it was so much better than not seeing each other. After our time together in May, we decided to block out our next get-together as accountability of sorts and make sure we took time to slow down in even the busiest of seasons.

How about your team? Do you have enough quality, unstructured time together? Can you think of a way to bring your team together intentionally in 2023? It doesn’t have to be anything fancy. Start small if you need to: Maybe plan a meal at a local restaurant or rent a meeting room for a couple of hours. I do suggest that you at least get out of familiar surroundings (i.e. your own office) and go somewhere different together—that’s what makes this time together feel really special!

Speaking of taking time away, this is my last post before going on break next week. On our team, we take a few extra weeks over the holidays to disconnect, refresh, recharge, and spend time with our loved ones so that we can come back with full hearts, ready to dive into another year together.

Our break starts on December 19th, and we return on January 9th. But don’t worry: We have some jam-packed posts scheduled every week while we are gone to inspire you and help you get ready to tackle the New Year! Here’s a preview of what’s coming up in the weeks ahead:

• Dec 20th: My Quarterly Roundup, which includes a reflection of our Q4 wins, challenges, lessons learned, and more
• Dec 23rd: My Life Outside of Work Newsletter. This month’s topic is Money Mindset! (If you aren’t subscribed to that, you can do so here and click “Life outside of work.”)
• Dec 27th: The books and movies that inspired me most in 2022, in case you are looking for something to watch or read over the holidays
• January 3rd: A list of reflection questions to help you envision the year ahead, along with a roundup of content related to goal-setting and mindset

And just like that, I’m officially “signing off” from the blog until next year! I can’t believe 2022 is almost over. Where does the time go?!

I’m wishing you a happy, healthy, and safe holiday season. Even more importantly, I’m hoping you can take a little time for YOU to rest and recharge in the weeks ahead. You deserve it!

See you back here on January 10th. I can’t wait to do 2023 with you!?

Biggest hugs ever,

Kristen