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The Five Keys to a Successful Team Retreat in the Age of COVID

Team SPI group photo Denver silly

As you may know, Team SPI is completely remote! This means we don’t often get the chance to get together in person—except for our annual summits. During the challenging last ~two years of COVID, that in-person experience has been… hard to come by. That’s why this past summer, with vaccines finally a reality, SPI leadership felt it was important for morale and planning to get our whole team together in person safely if we could.

I’m Sara Jane Hess, and I am the senior production manager at SPI. It might seem odd that a production manager is talking about planning a team summit, but once upon a time I was the operations manager and planned several of our past in-person events. When our previous operations manager announced she was leaving, I stepped in to help plan this year’s summit and get all the details in place. This included finding and booking venues, restaurants, and activities, amongst other things.

In this post I’ll share the five biggest considerations that went into planning and executing what was ultimately a fun and successful retreat. I hope it’s helpful for you if you’re thinking about putting together your own in-person event for your remote team, especially in the era of COVID.

Table of Contents

  1. Pick a Great Location (We Chose Denver)
  2. Make Sure You’re COVID Safe
  3. Make the Most of Your Working Time
  4. Eat Some Great Food
  5. Have Some Fun

1. Pick a Great Location (We Chose Denver)

We considered a few different locations for hosting our retreat, including Columbus (where Matt lives) and San Diego (where Pat lives), but we ultimately decided to go with Denver, Colorado (which also happens to be where I live). 

We chose Denver for a few reasons, but the main one was that it was a more central location for all members of the team, given that three of our team members live in Denver or within a 90-minute drive of the city.

Choosing a place where employees already live isn’t a must, but it’s a nice-to-have for a few reasons:

  1. It makes planning for venues and restaurants easier as local employee(s) will be able to make recommendations.
  2. It allows the team to get to know the hometown of their fellow employee(s).
  3. It cuts down on some costs since local employees won’t need hotel rooms, flights, or airport transportation.

Again, having employees already living in your chosen destination is a nice-to-have. Once you’ve selected your city, you need to find a venue to host your team—a home base for all the activities of the retreat.

Why We Went with a Hotel

In years past we’ve had our team stay at large Airbnb houses. But because of the number of people on our team, we’ve required at least two Airbnbs, which adds complications like proximity to each other, who stays where, delegating a suitable common area for people to hang out during non-work times, making sure both Airbnbs are close to restaurants/other attractions… the list goes on.

We’ve had all those challenges with past summits, so this year we decided to use a hotel. I felt that it made more sense to keep everyone in the same place, give them their own private space, and still have them within walking distance of restaurants and attractions. Finance-wise, once the cost of multiple Airbnbs and additional meeting space are added up, they generally become comparable to a hotel.

 Here are a few key things to keep in mind when selecting a venue:

  1. Accessibility to the airport and other areas of interest.
  2. The venue should be nice—clean and comfortable with public gathering spaces (like a lobby, terraces, and/or rooftop deck).
  3. Cost. It needs to be affordable, obviously. We set a goal for the price range we wanted to stay within, then negotiated the price with the hotel, which was able to keep us in that range.
  4. Multiple offerings/uses in the same venue. For us, this was renting a conference room in the same hotel as the team was staying at. This allowed us to bundle costs, which allowed us to get a better rate for hotel rooms and the conference room, and allowed us to be in a location that limited exposure to people outside our group (and therefore COVID).

Speaking of COVID safety, our choice of venue was guided in large part by the need to keep the team safe while traveling and meeting up during a global pandemic. Let’s talk a little bit more about what we did to reduce our risk.

2. Make Sure You’re COVID Safe

I’m really hoping we won’t have to consider this in future years, but a lot of planning time went into making sure that we minimized our COVID risk during the trip. There were two main ways we did this: by requiring team members to be vaccinated, and picking a venue that would reduce people’s overall exposure. 

COVID Safety: Vaccination

We required that anyone who attended was vaccinated and could provide proof of vaccination.

We also made it very clear why we were requiring proof. It wasn’t because we didn’t trust people, but because we wanted to build trust among the team that we were trying to take care of each other as much as possible.

Those considerations went into choosing restaurants as well. I called all of the restaurants we ended up eating at ahead of time to make sure they had COVID policies in place like masking and distancing, and in some cases required vaccinations of customers or staff. We also ate outside whenever we could. That was a little tricky with the weather, but overall it went smoothly—and most importantly, no one got sick.

COVID Safety: Location

As I was planning the summit, I tried to minimize the number of locations our team would need to visit. So, we picked a hotel that was centrally located in the city, close to Union Station where everyone would be arriving and departing from. The hotel also had a conference room on site that we could use.

This accomplished a few different things. First, it gave people more time, especially in the mornings and the evenings before dinner, because they didn’t have to travel very far to attend meetings—essentially, just an elevator ride. It also kept them from coming into contact with a lot of different people.

The location we’d originally considered for our work time during the summit was a really cool coworking space that in normal times would have been perfect. But I’d been to that location before and knew that it was a maze of offices with a lot of people crammed into a small area. I knew that if our team met there, we would be coming into constant contact with any of the few hundred people who might be working out of there on a given day.

I felt it wasn’t a risk that was worth taking, so we consolidated everything to the conference room of the Rally Hotel. This ended up being a perfect solution because we were within walking distance of not only Union Station, but also some really great restaurants and bars.

I was really pleased with how it turned out —and I think the team was too. If we ever do another summit in Denver, I would definitely consider following this same game plan.

Related Reading: “5 Ways Entrepreneurs Can Conquer Loneliness and Feel More Connected

3. Make the Most of Your Working Time

Our team has the benefit of having run several in-person retreats in the past, and we’ve seen what works and doesn’t when it comes to the schedule and format of the business portion of the event. This year we tried a slightly different format from past years, and I think it was a success.

Our summit ran Monday to Friday, and Tuesday and Wednesday were devoted to working time. We typically use these working sessions to recap the year and start planning for the following year.

This year, Matt recognized that in past years we hadn’t accomplished as much business planning as we wanted to in these sessions. This was in large part because a lot of our meeting time typically involved leadership presenting to the team.

To counter that, this year we tried to “democratize” things by having each subteam (marketing, production, solutions, and leadership) run their own portion of the meeting to identify problems and opportunities in their respective areas. We also made these sessions interactive, so the whole team was involved in brainstorming ideas and solutions for each area of the business.

Scheduling was also important. It’s also difficult to carry the attention of the entire team for a long period of time, so we broke up the schedule with different activities and some downtime.

So what format should you choose for the business portion of your next retreat? It’s all about knowing your team and the goals you have for your time together so you can make the most of it. The best format is not going to be the same for every team, so my advice is to consider what’s worked (and not worked) for your team before.

4. Eat Some Great Food

Another challenge for us was finding restaurants that appealed to everyone. Our team includes people with dietary restrictions for gluten and dairy, as well as a vegan. So it was quite the process to go through and find restaurants that offered those options and also had a larger menu so everyone could find something they liked.

Thankfully, with Denver being a diverse culinary city, it wasn’t too difficult to find those kinds of restaurants. It had been a struggle in the past in other cities, but Denver offered a good spectrum of dining options. As a plus, I didn’t feel like any two meals or menus were the same, which has not always been the case.

What’s the key to a successful dining experience for your whole team? The main thing is just doing a ton of research. Talk to locals and find out what their favorite restaurants are. Also, for the people on the team with dietary restrictions, I presented the restaurant options to them first and had them give the okay before I announced the options to the entire team.

5. Have Some Fun

Especially after the past almost two years we’ve all been through, it felt super important to enjoy our time together. It’s important to plan in some time that doesn’t require much brainpower and allows people to get to know each other a bit more. In addition to our dinners out, which were great for team bonding, in the evenings some people did karaoke on the hotel’s rooftop deck, and one night we visited a “barcade.” We also took a whole day to visit Rocky Mountain National Park and had a great time hiking and picnicking.

One of my favorite parts of planning summits is to come up with gifts for folks on the team. It’s a lot of fun to figure out what people might enjoy and use again and again that would also remind them of our time together as a team.

In past years we’ve done tote bags filled with T-shirts, stickers, and pins. We kept with that theme this year, but we also gave some gifts that would come in handy during the trip, especially since we had a lot of people coming to Denver (5,280 feet above sea level) from lower altitudes. First-time visitors to the city (which several teammates were) don’t always think about the importance of adapting to the altitude, as well as the high levels of sunshine.

So things like water bottles, sunscreen, and chapstick were excellent additions to the gift totes we gave everyone. They’re all not only great gifts, but actually benefit the team and their health, especially in the first few days as they’re adjusting to the climate and terrain.

An In-Person Retreat Is a Lot of Work—But It’s Worth It

As you can imagine, a trip like this is a lot of work to plan and pull off.

It’s also definitely a large monetary expense. I was conservative in my budgeting and gave extra buffer to things like meals, which paid off since we came in under budget (which had never happened before!). And thankfully the payoff, which is measured mostly qualitatively, has always been worth it.

Also, knowing how much to plan is a balancing act. I tried to plan for as many things as felt appropriate, while also leaving time for chaos as team members’ personal preferences (like after-dinner activities and non-team meals). If you plan every single detail, the whole event can feel constrained and inflexible, which is never fun, so I try to only plan what I need to.

As for unforeseen hurdles, there really were not many, which was a little shocking. One that comes to mind is one of our team members joining virtually. It worked mostly well, with hiccups from a sometimes poor internet connection, and it was hard for her to hear teammates talking in the conference room. Beyond that, though, everything ran incredibly smoothly.

I hope this post was interesting and helpful if you’re thinking about planning your next—or first—in-person team retreat. I might go into more detail on how to plan and successfully pull off a team event in a future post, so stay tuned!

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