Essential Tips for Planning a Successful Company Retreat

Megan Bianco
March 28, 2023
May 31, 2022
7 min read

"Some of the best conversations and bonding happens over an impromptu walk during a break or a “feet in the pool” moment while folks are relaxing."

Going has been remote since day 1. While we love being remote and we’re really proud of the culture of collaboration we’ve built virtually, in person time has proven to be critical  to our innovation, growth, and team harmony.

We get together twice a year as a whole company. In previous years, we’ve gone to Mexico for an all-inclusive experience, in April 2022 we went to Wild Dunes in Charleston, SC, and in September, we’re heading to Zion National Park! We learn something new with each retreat, so we’re sharing a few of those lessons with you to ensure your retreats can be as successful as possible.

Set goals

Like any good project, you should have clearly outlined goals or measures of success. Your retreat is no exception. What are you trying to achieve? What is the purpose of your retreat?

Our goals for the most recent retreat we had in April were as follows:

  1. Celebrate the success of each other and Going over the past six-months.
  2. Create and build stronger and more meaningful relationships through in-person collaboration.
  3. Build trust, rapport, and shared understanding between team members, explicitly & implicitly.

Clearly outline expectations for work

We’re a consumer brand with millions of customers, so we’re committed to continuing to provide them the service they expect from us during our retreat. While we scale it back, we work with managers to outline “keep the lights on” work.

For some teams this means “inbox power hours” or QA-ing scheduled deal emails in the morning, for others, it’s a 20 minute check in at the end of the day to ensure candidates in the pipeline are well communicated with.

Provide space and time

It sometimes feels like a good idea to plan every moment of a retreat to keep everyone entertained all the time - fight that urge. Some of the best conversations and bonding happens over an impromptu walk during a break or a “feet in the pool” moment while folks are relaxing. We strongly encourage inclusion on all activities. If there’s a last minute event or something impromptu, a message should be sent to our retreat Slack channel so folks can join if they want!

Also keep in mind that reflection is important and some folks are drained by constant interaction. Be sure you’re providing time and space for your team to refill their energy and step away from the group.

Find the balance of work and fun

We used to do “all fun” retreats, but we actually received feedback from the team that they craved a bit of work time. Work conversations end up organically happening and structuring space for them has been effective.

We now dedicated 1-2 days for work while we’re at our retreat - for full company trainings or functional team days. Some teams take the time to record new TikTok content, some do in person retros of the past six months, some brainstorm how we can improve our member experience. We leave the agendas in the hands of the teams as success is going to look different for everyone.

Mix up the events, but don’t overdo it

This is a lesson we’re still learning. We’re a group of people who love all different types of activities. We have a tendency to try to do everything all at once because we want to experience all the place we’re visiting has to offer. However, folks have a tendency to sign up for every event, overexert themselves, then end up being too tired to do the next activity or join the team event at the end of the day. Limit the options, make them voluntary to join, and don’t try to pack a full day. A lot of times, folks end up just wanting to go for a long walk together or sit by the pool. Flexibility is key!

Set a budget

We set a budget of $2,500 per employee. The bulk of that budget is made up of accommodations because one of our requirements right now is that everyone has a private room with a door that locks and a private bathroom.

In April, we had 44 attendees to the retreat and our budget was as follows:

  • Accommodations: $44,621
  • We go for 4 nights, so this broke down to about $250/pp/night
  • Food & beverage: $25,882 (more on this later)
  • Flights: $17,199
  • Excursions/Activities: $7,425
  • Transportation: $4,745: If we’re not in an all-inclusive, we always rent at least one car - mostly for emergency use. We try to rely on Ubers or local transportation (Zion has a great bus system!), when necessary.
  • Swag & prizes: $3,000

Get crafty with food plans

The logistics for food is always one of the more complicated parts of planning a retreat. In order to support our budget, we try to do a mix of venue catered meals, which are typically the most expensive, flex meals for folks on their own, and small group meals. We’ve learned that the team generally prefers a smaller group setting for mealtime. We ensure each group has someone with a corporate card and set a per diem budget for each meal. If folks do a meal on their own, they’re responsible for staying within the per diem and expensing the cost.

Be sure to ask about food allergies and restrictions ahead of time. It’s important to confirm that folks can actually eat what meals you’re providing and if not, you plan in advance for that. For example, we did a low country boil on our last day; however, we have a few vegans in the mix and folks who are allergic to seafood - no biggie! We had the hotel provide us vegan meals and the low country boil made a separate plate without the seafood. Most caterers and vendors are willing to work with you, but they do need advance notice.

The other thing we do to try to mitigate costs when we can is make a Costco run! We keep snacks and drinks in someone’s room and have folks stop by in the morning or evening to pick up what they want. This helps keep our costs down but also ensures folks aren’t reaching into their own pockets for that afternoon pick me up as much as possible. One day we did a “grab and go breakfast” with muffins, eggs, and plenty of coffee and one day we ordered pizza and salads for lunch. Get creative as much as you can, but also be sure you’re not burdening your planner in having to cook or organize meals for everyone each day. 🙂

Measure success & reflect

No matter how many retreats you plan, each retreat is different so it’s important to gather feedback on what went well and what could be improved. We always send a post-retreat survey the week after while the experience is still fresh in our memory.

The survey consisted of nine Likert scale questions and three open-ended questions that asked what their most and least favorite parts of the retreat were and a question for any additional comments such as where they’d like to go for the next retreat. The best feedback comes from open-ended questions because each attendee has the opportunity to reflect on their their experience. Fight the urge to ask too many questions and try to keep the survey short! We keep our public retreat Slack channel active for folks to chat and reminisce about the retreat too. Here’s what we learned about our April 2022 retreat from the survey:

  • 98% of attendees felt we accomplished our retreat goals.
  • 100% of attendees feel closer to the Going team.
  • 86% of attendees thought the working day was useful and productive. (It was our first working retreat so this is a great starting point!)
  • 98% of attendees were able to find things they enjoyed doing during the retreat.
  • 98% of attendees felt the Operations team did a good job communicating expectations and to-do’s for the retreat.
  • And 100% of attendees had a great time at the retreat!

Post-retreat surveys are a great way to measure success, especially over time. However, the biggest measure of success is seeing the team bonding & engagement from the retreat shining through in the weeks that followed. Teams were excited to work cross-functionally and our fun Slack channels were buzzing!

One of our values here at Going is Continually Improve, so we’re excited to keep doing just that with every single retreat and seeing what lessons will be learned from our upcoming Zion retreat!

What lessons have you learned from your company retreats?

Last updated
March 28, 2023
Last updated
May 31, 2022
Megan Bianco
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