For some, the thought of attending a weeklong sleepover with your coworkers sounds like a nightmare full of forced, corny team building activities.

But it doesn’t have to be that way! If you’re in charge of planning your company retreat, you have the opportunity to introduce new team building and leisure activities that are productive, memorable, and most importantly, fun.

So you’re having a company retreat

Planning a corporate retreat that goes beyond a boring, booze-soaked week of R&R on the company dime requires intentionality and attention to detail.

We’ve talked about the logistics of planning a corporate retreat before (Zapier also has a great guide to retreat planning), but once you’ve taken care of the basics, you need to figure out what your team is going to do. This can feel like the most daunting task since you’re trying to appeal to your entire team’s expectations, but fear not! It can be done.

Easy ways to use video to boost company culture all year round

After five company retreats, we’ve learned a lot — for example, people don’t like to be on a bus forever and ever (who knew?!) and prefer only one deep dive talk scheduled at a time, so nobody misses out on any of the brilliant ideas our team members have to share. The surveys we conduct after each retreat have helped us apply that feedback to the planning of future retreats, and our ratings have risen from 8.87 to 9.5 out of 10.

The recipe works. By sharing it, we hope to save you some major headaches.

How long should my company retreat be?

Our first four retreats were four-day, Tuesday-Friday affairs. We thought this would be enough time to work, bond and respect work-life balance. But while four days is probably sufficient for co-located offices, our remote team is spread out all over the world, which meant the first day was always lost to travel.

This fall we experimented with a full workweek retreat (Monday-Friday), and the post-retreat survey sings the results: Adding a designated travel day and three full days at our offsite was the perfect amount of time to get work done and have enough time to get to know each other.

Scheduling like a boss

Once you have a large group of people together in the same place, how do you keep everyone in the know about what to do and where to go during your corporate retreat?

We use Google Calendar for our meetings and events at Help Scout, so to keep things simple for our team, we create a “Retreat” calendar to share retreat events and their locations. We share the calendar two weeks in advance, so our team has all the necessary info and People Ops doesn’t have to answer the same questions over and over (not that we mind!).

Retreat activity schedule

Planning your corporate retreat activities

It’s critical to plan for the right mix of business, activities and free time. While talking shop is certainly a priority, the goal of our retreats is to relax and connect in real time. This may sound obvious, but you need to actually schedule opportunities for this to happen. Whether it’s gathering before dinner to hang out for an optional cocktail hour, having s’mores by a fire at night, or leaving the hotel for longer group adventures, it’s essential to offer a variety to please all personalities. After our most recent retreat feedback, our next retreat will have even more scheduled “free time” for more organic bonding opportunities.

Help Scout hikers

Some adorable Help Scouts take a hike

Business in the front

All-hands meeting

We kick off our first full retreat day with our all-hands meeting, when each team lead gives a big-picture talk about what their team has been up to and where they’re headed. The all-hands meeting is equal parts pep rally and important business updates, which sets the tone for our week together.

Team time

It’s critical for each team to have dedicated opportunities to meet and plan for the future. For remote teams, this face-to-face time is even more important. Even if your company is co-located, dedicated team time is still an important opportunity to brainstorm outside the office in new surroundings to inspire new ideas.

Team time

Deep dive talks

A few weeks prior to the retreat, I share a Google Sheet asking the team to nominate a speaker from the company and a topic they want to learn more about. After a weeklong nomination period, I take the top 10 suggestions, create a Google Form, and ask everyone to vote for their top five talks. The winners prepare a 30-minute presentation on their topic.

At the most recent retreat, the deep dives covered everything from the art of storytelling, to how to have difficult conversations, to our rebrand, to where we’re headed with the Help Scout mobile app. The deep dives teach us something new, and they shine a spotlight on team members in a special way that’s hard to reproduce once we’re back to our normal grind.

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Support power hour

You might be thinking, what happens to our customer support if the company is off galavanting in the hills of Quebec? If you’re like us, then you turn tackling the queue into a whole-company activity! We call it “Support Power Hour,” and we incorporate it into our retreat planning. We even dedicate a room to it and jump right in to help our customer team.

Retreat tip: Plan for customer support coverage during your company retreat and involve the whole company.

retreat support coverage

Party in the back

(Okay, so we really aren’t a partying company, but I wanted to continue the mullet metaphor.)

Retreats are a rare time when spontaneous moments arise and hilarious memories form. The major reason we retreat is to spend quality time together in a beautiful environment. It’s all too easy in a remote company to stay heads down in our work, so we make a point to schedule plenty of fun time together, too.


On our fall retreat a year ago, some of us stumbled upon a bar that was having a karaoke night. What could have been an awkward evening turned out to be both hilarious and endearing — not to mention we learned we have teammates with serious pipes! This serendipitous night of song led to a planned karaoke night at our last spring retreat, where we hired a DJ with the equipment necessary to host our own karaoke party at our hotel. We repeated it again this fall, and now karaoke has become a beloved part of our retreat ritual.

Retreat tip: As with any activity you offer, make participation encouraged, but never mandatory.


Like many companies, we have a dedicated channel in Slack where anyone can share a compliment about another teammate, work-related or otherwise. We call it #WarmFuzzy and at our most recent retreat, we decided to have a spontaneous moment after our closing dinner to have an in-person #WarmFuzzy open mic. We weren’t sure what would happen, but sure enough, many people felt inspired to give thanks and praise to others in the room, leaving everyone feeling … well, warm and fuzzy!

The best part: Many shared sweet shoutouts to people not on their own teams, demonstrating just how effective a week of bonding has on cross-team culture.

The last hurrah

Since the first half of the week is dedicated to travel and business/learning, we leave Thursday open for one last big activity that requires a lot of time. Well before retreat time, I research what options exist at or near the hotel and then send out a survey to our team to gauge interest and popularity. Depending on the results, I offer the top 2-3 options so people can choose what appeals to them most. In the past, we’ve gone on long hikes, half-day sea kayaking treks, foodie tours to local producers, and high ropes course challenges.

Sampling food at a farm in Quebec. Pâté on! Some Help Scouts sample the goods from a farm in Quebec.

Dancing with myself

Even if you think you’ve figured out the most exciting activities under the sun, it’s important to remember there will always be a few people who might want to sit things out, and that’s okay! Spending every hour with 50+ other people, several days in a row, is certainly not everyone’s cup of tea. But the best retreats are ones with optionality; if you provide variety while allowing people to make their own choices, you’ll have happy teammates who feel rested and listened to.

Shake it like a Polaroid picture

Since corporate retreats typically only happen once a year, it’s essential to document those moments to inspire your team throughout the year. But company retreats offer more than just adorable photo ops; getting your teammates out of the office and into a fun, new location brings out the spirit of your company! Genuinely happy people make great team photos and b-roll, and yes, great assets on any “About Us” page. One of the best recruiting aces to have up your sleeve is to share a video that brings your company culture and energy to life. Not to mention, the photos make for adorable fridge magnets and gifts for your team.

Photo fridge magnets

A collection of Help Scouts from the past three retreats!

Help Scout Support Team

Despite what it looks like, we don’t do trust falls on retreats!

In the past, we hired a professional video crew to create a video of our company retreats. We even use it on our “About” page to share an insider look at our company and attract top talent.

And if hiring your own video team breaks the bank, don’t worry! There’s a good chance someone on your team has a passion for video and might want to put something together in-house. For example, I took over our retreat video after our most recent voyage to Quebec:

Retreat teasers

Because we’re a remote company, we can’t build hype about our upcoming retreats during in-office meetings or over the lunch table. So once again, we use video to entice our teammates to start the countdown to retreat time.

Retreat teasers are also a great way to highlight a fun feature about your destination. For our Austin retreat, I really played up the Old West theme. For our most recent trip to Quebec, I employed some gentle self-deprecation as I tried to tackle YouTube French lessons.

Don’t forget you probably have a wide array of personalities on your team, and they might have fun hobbies or gadgets they’d be willing to bring along to enhance the retreat experience. Special shout out to Brett who brought his drone!

After the show

Survey, rinse, repeat

We didn’t get to this formula alone. I survey the team after each retreat so I can continue what works and adjust what didn’t. I also love using Typeform for this since it’s easy to use and lets me do fun things like this — see how the professional photos come in handy?

Retreat survey

Until next time

Without thoughtful planning, company retreats have the potential to overwhelm and exhaust, leaving your valued teammates feeling annoyed and resentful. A successful retreat requires a schedule balanced with meaningful work time, a variety of activities, and plenty of free time. (Exquisite accommodations and good food don’t hurt, either.)

Leah Knobler

Leah Knobler

Leah is on the People Ops team at Help Scout. She loves building a talented, diverse team that puts customers first. Connect with her on Twitter and LinkedIn.