Planning a company retreat

Illustration of a team around a pool with laptops, sticky notes, and a white board.

We just got back from our 10th Wildbit retreat. It was clearly one of (*Tim Cook’s voice*) Wildbit’s best retreats to-date. Why do I say that? Because we went to Disney! Okay, there are more legitimate reasons, like we brought together 23 team members from all over the world, and had a productive, fun, and relaxing time. Yes, it’s totally possible to accomplish all three, but it takes a ton of planning. It requires preparation—lots of it. It also requires thinking about every possible detail and scenario and having a plan for it. But to pull a successful retreat off you must be extremely flexible because plans don’t always go according to plan. 

Maybe I should first tell you a little about myself, I’m Britt. I am the get-it-done, magic maker, behind the scenes elf at Wildbit. If it doesn’t have to do with development or design, chances are I had a hand in it. I manage the office, onboard new team members, and take care of non-product focused logistics, including retreat planning. This is the 4th retreat I’ve planned at Wildbit. So how do I do it?

  • Who: The entire team, minus one who couldn’t make it because of extenuating circumstances. 
  • What: Wildbit yearly retreat 
  • When: 7 nights in April (I explain how to select dates later)
  • Where: Reunion, FL - We had to stay in the U.S. this time because of some VISA issues (this is the flexibility I was referring to). We stayed in two houses, one we dubbed the main house (pictured below), and the other was just across the fairway. 
A photo of the main house we used on retreat.
The team was large enough that we had to have two houses, but we did all of our team activities in the main house which was larger and better for accommodating team activities.

But before I get to the why and how here is a fun infographic to help you visualize what a Wildbit retreat is like! Did I mention we went to Disney?! I try to plan one big excursion to get everyone out of the house. It just so happened Disney had a special event going on at the same time, allowing us to enter the park at 7pm and stay for extended hours. We closed the park down at 2am and were 23 out of 500 people in the park. It was a really amazing experience, although I’m sure the team members with children probably got some side eye when they got home. 

Total cost: $40,204.70, Flights: 60, Dima was the record holder for holding his breath under water at 2:47, and said you have to have patience, and make it past the shaking, Space Mtn: 82, Free Ice Creams: 36, Post its used: too many to count, Cups of coffee: 387, Beer: 516 bottles, Wine: 23 bottles, Trips to the store: 17 Impressions of Trump: countless, Broken French Presses: 1, Loads of Laundry: 34

Why? 

We go on retreats for a multitude of reasons, but the most important in my opinion is getting the entire team together in one relaxed space where no one has to stress over day-to-day tasks. It’s a time where we put names to faces, get to know each other's personalities in real life, and of course plan for the growth of the products. There is just something magical about getting the entire team together.  

What's the budget?

Who goes? 

At Wildbit our whole team goes, but families do not. We use this time to dig a little deeper into the difficult discussions, like how we communicate at Wildbit, product roadmaps, and larger collaborative meetings that can’t take place when we have our heads down in the products. 

How many days should it be?

We’ve found that the sweet spot for retreats is 7 nights. Most vacation home rentals prefer a Saturday to Saturday stay. It helps the people traveling a long way adjust and get over the jet lag, as well as give the team time to warm up to each other. The seven days really work out to 5 days of meetings and actual retreat time, because day one and day seven are for travel. We’ve had longer retreats, but have found that by day seven we’ve accomplished what we needed to as a team, and everyone is ready to get back to their families and their own bed. 

What should we spend per person? 

On average, we spend $2000-$2500 per person for destination retreats and try to remain in that budget as our team grows. When we bring everyone to headquarters it’s less than a third of the cost. This Orlando trip worked out to $1,748 a person, even with Disney! On average the housing and flights account for at least 50% of the budget, food and beverages 25%, and the remaining 25% for ground transportation, excursions, individual travel expense reimbursements, and incidentals.

When should we go?

Consider seasonality.

Picking a location depends on the time of year, and seasons. Make sure to research the area and find out what the weather will be like when you plan to go. Of course, you can book a tropical location in the offseason to save a ton of money, but is it worth it if your team is stuck indoors for the duration of the trip? We’ve made the mistake of searching high and low to find the perfect house with an amazing pool, only to get there and realize it was too cold to swim. 

When was the last retreat?

You’re asking your team to leave home and family obligations so it’s important to space retreats out, and be considerate of everyone's personal lives.  Make sure you aren’t going just to “go,” plan retreats when they are necessary. We’ve found that yearly seems to be working well for us, and when needed we bring in smaller teams to HQ. For instance, we had the Customer Success team in Philly in January. 

What do your products need right now?

If the previous retreat left the products in a position to move forward for the year, and the direction doesn’t need to be revisited, once a year is totally fine. Sometimes it’s necessary to have a retreat two times a year, and sometimes not. 

Do we have a lot of new team members?

The direction of your products might be stable, but you may have just hired six new people since your last retreat (Wildbit is in this boat). Having a remote team, it’s important to get the everyone together in person. Knowing each other in real life helps the development process, and online dynamics/communication.

When does the team have the most availability? 

We understand people have lives outside of the office (kid’s birthdays, vacations, anniversaries etc), so picking dates means we have to take into consideration the schedules of each of our team members. I suggest trying to keep retreats in the same months each year, and at least six months out placing a “hold” on two separate weeks with the team so they can plan ahead. 

This is part of that flexibility I mentioned at the beginning of this post. Having two weeks set aside saved us this year. We were all set to book a house, and in the half a day it took me to find a second home to fit the rest of the team, the main house was booked by another group. Because of this, I asked the team to hold next April as our retreat month, and we’ll narrow the dates down as we get closer.

Where should we go?

Where are there homes large enough?

We try our best to give everyone their own room, and we try to all stay in the same home, so our downtime is spent bonding, and relaxing. Having a large enough space with seating for the entire team for meetings and meals is also important. 

Is it near a major hub?

Try to stay near a major transportation hub, so the majority of the team can get there quickly, and so we don’t have to spend hours after our flight getting to the house. Sure a remote island sounds amazing, but when it takes 10+ hours to get there you’ve already burned 2 days traveling.

Factor in VISAs for international team members.

Having a remote team sometimes means VISA restrictions depending on where they are from, so it’s important to know this ahead of time. I keep a list of restricted countries for our international team. I also reach out to them early on in the retreat planning process to let them know the location we are considering to see if there are any conflicts. I also ask them to check VISA processing times of the countries we’re considering. Some countries require you to travel to their embassy to have an in-person interview while others can be applied for online. Because there are so many variables, I really rely on each individual at Wildbit to be their own expert. 

Wi-Fi

Wi-Fi is important. We don’t work all day, but being able to help our customers, fix any issues quickly, and being able to reach our families is incredibly important. Even if the house says it has Wi-Fi, it’s important to have a backup plan. Even in Orlando we had to tether when too many people were online at the same time.

Transportation to the retreat and during the retreat

How long are the flights?

Some of our remote team has limited access to major transportation, so making them travel for 24+ hours is unrealistic. We try to keep total travel time as short as possible, for as many people as possible. If that’s not possible, we work around by having people who don’t have great flight options come to headquarters a few days before the retreat, and if necessary a few days after. This allows them to adjust to the time zone, relax, work with the team from Philly, and breaks up the travel time. 

Can we get direct flights?

To try to alleviate the long flight issue, we always try to book direct flights, the most direct flights to vacation destinations tend to be on Saturdays, so we usually book our retreats Saturday-Saturday. 

Try to have everyone arrive near the same time

This might seem like it’s not a big deal, but it actually is. Getting people in at the same time or in groups reduces the additional costs for transportation to and from the house/airport. If people come in scattered it requires a lot more on the logistical side for planning everything from check-in time, transportation, and meals. It could also mean someone is stranded for hours alone in the airport waiting around for the rest of the team. 

Rent cars vs. Shuttle 

This depends on where you are going, and what you plan to do while on retreat. Rental cars are a great option in a place like Europe where it’s very drivable and necessary to explore the country. If you are going to a location at a resort cars really aren’t necessary because everything is in one place. Figuring out and comparing the numbers and scenarios ahead of time can save a lot of money in the long run. 

Meals and accommodations

Convenience of hotels vs. camaraderie of a house

We fully believe that a house or two houses are hands down better than a hotel. The space to spread out, have meals together, swim, play games, and meet really helps foster the group atmosphere. Hotels just don’t foster the same type of environment.

“Until going on the retreat, I didn’t fully appreciate how much of a difference it makes being in a house together rather than individual hotel rooms. Having all of the rooms in close proximity to so much shared living space made for a much more serendipitous environment to hang out and spend time getting to know each other than if we had individual rooms scattered throughout a hotel.” -Garrett Dimon, Marketing

Eating out vs. eating in

Eating in is almost always more cost effective, and we try to do that as much as possible. If the house comes with a chef, they usually offer price-tiered menu options, so you can work in one or two fancy meals and still stay within your budget. Shopping at big box stores, and buying in bulk helps keep costs low. Also, if you are abroad, sticking with local cuisine and ingredients helps keep costs low as well. Eating in also reduces the stress of finding food or restaurants that can accommodate such a large party. It might sound silly, but knowing what you are eating and at what time is important. I include meal times and the menu in our retreat itinerary. Eating in also brings the added benefit of plenty of leftovers for when people are hungry between meals.

Cooking as a group vs hiring a chef 

Usually, we have a chef who prepares breakfast and dinner, taking the burden of what are we eating, when are we eating, and who is cooking out of the equation. It also helps save money in the long run, so you aren’t tempted to order out for every meal. For lunch, we have a bunch of options and people make their own sandwiches, salads. Or we cook as a group, taco Tuesday, hot dogs and hamburgers on the grill, etc. 

Food restrictions

It’s important to ask ahead of time if anyone has food restrictions, it makes planning a lot easier and takes the stress off those individuals.  Also letting everyone see the menu before retreat helps catch issues before they arise.

Work or play?

Structured meetings

Having a plan for meetings is extremely important. It helps everyone come prepared so we can be productive. We are very detailed with agendas, who should be in attendance, and what we hope to accomplish. The person running the meeting takes notes, and when we get back that person is responsible for posting a summary including any action items. We like to have days dedicated to products, so the other product teams can have side meeting or downtime. 

Group Meals

Everyone is expected to be present for meals. Sharing meals with the team helps bring everyone together in a relaxed environment. We try to create a family friendly environment and culture, and we like to extend our family lunches in our Philly office to the entire team on retreat. We tell funny stories, toast to successes, and enjoy each other's company. It’s also a good time to go over the day’s schedule and make changes as necessary because everyone is present. 

Unstructured downtime

We don’t fill the down time with a million activities, we allow the team to spend that time as they see fit. That could mean one person is napping, a group is playing poker, and another group is in the pool, and so on, which is totally fine because it allows the team to recharge and unwind. But you should make sure there are enough options. Our house on this retreat had a theater, poker table, pool, TVs and gaming systems. 

Planned Excursions

I try to plan one outing each retreat, and I try to keep it a surprise. Excursions can be expensive and a take a lot of time, so thoughtfully choosing something special for the entire team isn’t easy, but it’s worth it. I mentioned earlier that we went to Disney on this retreat, and it was a once in a lifetime experience. My original plan was to take the team to Epcot and play the beers around the world game, but when I called Disney to discuss ticket prices, they told me about the Disney After Hours event. The price was a little bit more, but it was so worth it! 

A lot of the team had never been to Disney, and being able to be in the park with only 500 people was amazing. There were no lines, so some of the guys rode Space Mountain 7 times in a row. A big group of us rode Splash Mountain multiple times without getting out of the boat.  All 23 of us crammed into one boat on It’s a Small World, which is a memory that will last a lifetime. The ticket included unlimited novelty ice creams, and bottled water, which we definitely took advantage of. The majority of the team was beside themselves with the magnitude of this surprise, I don’t know how I’m ever going to top it!

Photo of the team at Disney World.
The team excursion to Disney late night was a great chance to hang out and let loose.

What would I have done differently?

Although I think this retreat was pretty amazing there were little things I think would have made it even better. 

  1. Shuttles. When I started planning flights, I didn’t do a lot of research on transportation from the airport because the house is 30 mins away. I assumed it’s like Philly and the taxis would charge a flat rate, but that is not the case in Orlando. I had the team coming in at different times rather than in one large group, so a few of the of the guys had to wait for a while in the airport to take a shuttle with the rest of the team. 
  2. Coffee!!! I’m not a coffee connoisseur, but it turns out almost everyone else on the team is. The house came with a Mr. Bunn and a Keurig, which didn’t go over too well. I think next time I’ll either tell the team to pack their own tools (which some did), or bring a french press and good beans from home. 
  3. Menu design. I would have arranged the menu much differently by starting the week out with the heavier meals and making the meals lighter as the week went on. 
  4. Housekeeping. In the past the homes we’ve stayed in had some form of housekeeping, this one did not. Picking up after 23 people is a full-time job, so next time, if the house doesn’t come with housekeeping, I would probably schedule someone to come at least once or twice. 
  5. Bathrooms. Four dudes cannot, I repeat, cannot share one bathroom 😃 

If you’ve never planned a retreat, start small. You can always add more bells and whistles the next go round.  This wasn’t our first rodeo, so we’ve learned to factor in quite a few considerations. 

Here's the full history of our past retreats with links to more information where we have it:

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