How to Plan Fun and Productive Company Retreats

Leah Knobler | February 9, 2016

The company retreat, often imagined as a weeklong playground of corporate hedonism and zero work, is slowly getting a much-needed makeover.

At Help Scout, we’re taking steps to rewrite this narrative by meticulously planning our company retreats to result in thoughtful, effective getaways that spur productivity, juice up morale, and lead to more meaningful relationships. These types of details are critical whether you work together in an office or you’re a remote team, like we are.

Why retreat?

Like other remote companies, we rely on many tools to stay connected and organized as we work.

But there’s a special magic that happens when we get the entire team together in a room, on a ski slope, or in a bowling alley on our retreats.

Figuring out each other’s personalities face to face offers helpful information to take back when we resume our largely text-based communication. For non-remote teams, a retreat can help shake up the status quo and get creative juices flowing in an environment that’s not the staid, old office.

The past year at Help Scout has been filled with incredible growth, resulting in a fall retreat in Portland, Maine, that doubled in size from the previous spring. Planning a company retreat that leaves your team invigorated has its challenges, and with three under our belt, we’ve learned a great deal.

Planning the big event

One of the most useful things I learned as a high school teacher was the concept of differentiated instruction—not every student learns the same way, so the act of teaching benefits from a variety of approaches to present any given topic.

As I planned our recent fall retreat, I kept this idea in mind: How do I take 34 people with different tastes and successfully plan for food, fun, and ways to recharge that they’ll all enjoy? Much like differentiated instruction, differentiated retreat planning is the best approach—providing variety and choice will result in maximum happiness and a trip everyone will remember.

With this philosophy in mind, let’s talk details: setting a budget, picking a location, finding a place to stay, and structuring those memorable activities.

Budget:

Retreats don’t have to break the bank. To determine a budget, consider your company size and where you want to go. If your company has never retreated before, start small.

For our first retreat in September 2014, we rented a few houses in Provincetown, Mass., and kept things simple. After that, we stepped it up and stayed on a ranch in Colorado. If you’re a remote company and still concerned about the price tag, keep in mind that it’s less expensive to fly everyone someplace twice a year than to pay rent on an office space year-round.

Location:

While it might seem appealing to travel to a five-star tropical resort that’s only accessible by helicopter, we’ve learned that getting to the retreat location is as important as the retreat itself. Finding places near major airports and within a short drive helps your teammates feel relaxed and happy they’re about to spend time with their colleagues. And you’ll never know until it’s too late that someone on your team might get motion sickness, so the less time on a bus, the better.

Accommodations:

While costlier, staying in top-notch accommodations sets the tone for your retreat. An impeccable hotel that pays attention to detail will wow your employees, raise morale from the start, and encourage everyone to bring their A-game. While it’d be great to scope out accommodations ahead of time, that won’t always be doable, so relying on travel-review sites such as Trip Advisor and Yelp are essential.

We also prioritize allowing every employee a private room. Again, it increases the budget, but we’ve found that our team greatly appreciates some quiet time and the chance to recharge alone.

Structuring activities:

Unless your team is comprised entirely of extroverts, it’s important to schedule time to bond together as well as unstructured free time. Spending several high-energy days with your colleagues has the potential to feel draining, so providing your team with choices in how they spend their time will add to employee delight. Just be crystal-clear on which activities are mandatory and which are not.

Figuring out group meals can be one of the most daunting yet exciting parts of retreat planning. We’ve found that surveying everyone on your team before the retreat about food allergies or dietary restrictions goes a long way to ensure restaurant selections meet everyone’s needs. And it’s helpful to have these on file going forward (in case you someday want to send cupcakes to Amanda in Paris, you’ll know they have to be dairy-free!).

Enjoying some bonding time at Maine Craft Distilling, Portland, Maine.

While the main reason we retreat is for everyone to build deeper relationships, we also talk shop. We structure time for each team to meet and, for our upcoming spring retreat, we already have ideas for more cross-team interaction as well as spontaneous deep-dive talks in more casual settings. Scheduling team-meeting time is also great for big-picture visioning and strategizing, which energizes everyone to return to their remote offices with refreshed goals and attitudes to execute.

But all work and no play makes Jill a dull girl. In between the meetings and meals, plan a few non-business activities for your colleagues to participate in. Think of activities that are exciting, potentially out of the ordinary, and also accessible to the greatest number. No, I’m not talking about trust-falls or mandatory karaoke. While there’s nothing wrong with offering opportunities to drink, don’t make assumptions that your team is full of boozehounds. Trust your team to make adult decisions, but also set everyone up for awesome, safe fun by capping open bars or handing out drink tickets. In the event you do have people who are dying to sing karaoke, make it happen, but make it optional.

A smile-inducing trek to picturesque Portland Head Light.

No such thing as over-communication

Getting all of our non-Boston based employees to our HQ on the right day and time takes organization and patience. About a month before the retreat date, we share a document in Slack with all the pertinent info—location, dates, tentative schedule, etc. We issue each employee their own company credit card, so everyone is able to find flight schedules that work best for them and purchase them easily.

Leading up to retreat week, we create short video teasers to add some pre-retreat hype, as well as to remind the team of any updates. Part of the differentiated retreat planning involves sending information in a variety of ways, so the more the better.

As your company gets larger, getting your team where they need to be can feel like herding cats. To tame the pack, we give each employee an individualized retreat schedule in a fun goodie bag. We send the same schedule to everyone through email as well as on Slack. Again, reaching people in a variety of ways helps everyone get to the right place at the right time.

During the retreat, Slack can be a huge help to rally everyone in the lobby or to send schedule updates in real time. And to ensure variety, we aim to make one mini video update mid-retreat.

That’s a wrap

Organizing and executing a company retreat is equal parts exhausting and exhilarating. But once it’s over, quickly solicit feedback from your team to improve the next retreat while showing your team you value its input. Don’t take it personally if some people don’t love every part; differentiated retreat planning requires being at peace with the fact that everyone will enjoy things differently, and that’s great.

When planned with intention and consideration, a company retreat provides an authentic opportunity to boost employee happiness and build a strong, connected culture—and it shouldn’t require a six-figure spa bill to pull it off.


About the author: Leah Knobler is on the People Ops team at Help Scout. She spends her days making sure everyone around her is happy and set up for success.