This Is How We Offsite: Enhancing Employee Experience Through Effective (and Fun!) Team Retreats

When People Teams think about employee experience and employee engagement, they typically focus on objectives that fall within the confines of the office: When is the next happy hour? How do we create more facetime with leaders? What are our communication best practices?

But, just think—What could you gain if you pull your team away from their desks & their work and get them outside the office and out of their comfort zone?

As a member of the Employee Experience Team here at Greenhouse, I have a hand in organizing many events across the organization. One of those, in fact, was a recent offsite trip. Our 22-person G&A team trekked outside NYC to the Poconos for our first annual departmental retreat. Some participants were excited about spending time together; others were worried they would be forced to do trust falls; and one (me) was terrified that the trip would be a bust. Spoiler alert: We had a blast! And through the process of planning the trip, I learned a lot about what it takes to orchestrate a successful event and contribute positively to the employee experience. When you take employees outside the office walls, they can connect on a more personal basis, and this is exactly what we hoped for.

Below are 5 tips that will help you plan your own fun and most importantly—effective—team offsite!

1. Figure out what you’re trying to accomplish

Before you start planning your event, it’s important to create goals for your time together. Do you want to improve team communication? Increase bonding between new team members? Work on conflict resolution? Before we started planning the logistics of our offsite, our VP of People, Maia Josebachvili, and I sat down to map out the objectives for our time together. We determined that we wanted to accomplish 3 things:

  1. Co-workers get to know each other and build rapport. Our G&A team is split between our San Francisco and New York offices, and with all the growth we’ve experienced over the past year, we haven’t all had a chance to get to know new team members as much as we would like. Our SF crew was flying in for the event, making it a perfect opportunity to build connections across the two locations.

  2. The team feels like a “team.” There are many definitions of what “team” means. For the purposes of our offsite, we defined this as “an increased desire to cooperate and help each other out.” Simply put, we wanted the team to work well together.

  3. A sense that the event was “time well spent.” There is no worse outcome than team members walking away from an offsite feeling as though their time was wasted. We hoped our team members would walk away from the event feeling that the offsite was a valuable use of their time, and not a distraction or inhibitor from completing their work. I would argue that any event should have this goal!

2. Find the right time

Nothing dampens the spirit of an offsite quite like participants obsessively checking email, making phone calls, or rushing to finish projects in-between activities. If you are holding your offsite during the work week like we did, you won’t be able to completely avoid this, but with some planning and strategic scheduling, you should be able to minimize conflicts.

  1. Set a date at least 2 months in advance. How far in advance you need to give participants a heads up depends on the size and makeup of your team, but a good rule of thumb is more forward notice = more participation.

  2. Take into consideration the unique time constraints of your team. Inviting the sales team? Steer clear of the last few weeks of a quarter while they log those last minute sales. Finance team joining in? They are probably closing the books during the first few weeks of the new quarter. Each department has their own ebb and flow, so talk with participants if you aren’t sure about their schedules and make sure to plan accordingly.

Budget Tip #1: Accommodations tend to be cheaper during the week, as opposed to a weekend, and planning a few months in advance gives you more time to negotiate a deal.

3. Get (a little) uncomfortable

In 1974, Donald Dutton and Arthur Aron studied the effects of fear on attraction and found that individuals are more likely to be drawn to someone when placed in a scary situation. While I don’t suggest incorporating a fright fest into your agenda, this study taught me a lot about the effect of environment on connection. What I took from this study when planning the offsite is that lasting memories grow out of shared experiences that present a challenge. Each team will have a threshold for discomfort, and it is important to understand where the line falls. Not every group will benefit from trying to scale Mt. Everest or a walk over hot coals, but a few bug bites, bunk beds, or scrambles up a hill can actually help bring your team closer together and create lasting memories.

4. Give everyone a job

Team bonding isn’t all about the games. Planning an offsite provides plenty of opportunity for collaboration and teamwork. Here are a few jobs that we doled out:

  1. Food planning & prep. Offsites are a great opportunity to bring out some of the lesser known talents of your team members. For instance, our Recruiting Manager Jacqui Maguire is a former restaurant manager and pastry chef. Imagine our luck that she agreed to oversee all food planning and preparation at the offsite. With Jacqui at the helm, a team was assembled to prep and cook the food, which resulted in an incredible meal that we enjoyed together.

  2. Transportation. Executive staff are not exempt from getting to work at a team event. When we decided to rent two 16-passenger vans as the most cost effective option for shuttling the group back & forth from the cabin, there was no question as to who would get behind the wheel. Maia and our VP of Finance Pat Leahy not only transported us back & forth safely, but they also lead classic road trip games and raucous sing-alongs, making the 2-hour trip part a memorable part of our experience.

Budget Tip #2: The more DIY you can encourage, the more money you will save. We had all our ingredients delivered to the office the day before our trip and cooked everything ourselves. We also opted for renting passenger vans vs. a party bus or chauffeured ride.

5. Focus on team-building that doesn’t suck

If you’ve ever been in charge of planning a group retreat, chances are you’ve googled “team building activities that don’t suck,” and come up with very little usable content. We all want to avoid lame, cookie cutter games (and minimize employee eyerolls), so how do we facilitate awesome employee bonding and keep teams engaged through play? Here are 3 points to keep in mind:

  1. Be inclusive a diverse set of talents. What do an athlete, artist, problem solver, and movie fanatic have in common? They are all showing up to your offsite. Your team is comprised of unique individuals with different skills, passions, and experiences. When planning team building activities, make sure you incorporate events that take this into consideration and allow everyone to succeed and contribute in their own way, whether it be through athleticism, creativity, problem solving, or other talents.

  2. Tie it back to the company. Offsites are a perfect time to test employees on essential company information, as well as bring new employees into the know about the history of the company. One of the easiest ways to do this is through a trivia challenge. Along with regular trivia questions, we peppered in some Greenhouse specific questions, like “What is DaJoCo?” (our company’s original name), “Which 6 attributes are a part of our culture credo?”, and “What year was Greenhouse founded?” We ended up calling Jon Stross, our company Co-Founder & President for the tiebreaker.

  3. Collaborative competition: There are a lot of strong feelings about the use of competition in team building. Alexander Kjerulf, founder of Woohoo Inc., wrote a great article about the detriments of pitting team members against each other, yet almost every list of “team building activities” is chock full of highly competitive events. When Maia and I sat down to talk through the activities list, we decided to marry both competition and collaboration. While we did divide our group into separate teams, and awarded points to event winners, we also created a set of secret “character cards” that would reward individuals for displaying good sportsmanlike behaviors towards opposing team members during competition, such as cheering on another team’s victories, helping an opposing team member, etc. These points were significant enough en masse that they could put teams in the lead. When it came time to crown a winner, we announced each team’s event scores, and then added on their “character score.” It is no coincidence that the team who won the overall games also had the most character points.

Budget Tip #3: Repurpose stuff you have around the office, and ask coworkers if they have supplies at home. Many of our team members brought their own air mattresses, games, or camping supplies, and we went through the closets to find many of the supplies we needed for our field games. (See the Appendix for the games we played and the supplies needed!).


Final thoughts

After the games are played, the marshmallows toasted, and the campfire put out, how do you know that it was all worth it? Since returning from our offsite, participants have told us that, because of our time in the woods, they feel closer to their co-workers, a stronger connection to the team, and more comfortable approaching our departmental leadership. We even have an internal Slack channel where we share photos, inside jokes, and, of course, the beginnings of a plan for our trip next year.


Appendix: 5 team-building games

1. Team Crest, Name, Motto & Fort-Building

  • Timing: 15-20 minutes

  • How You Play: Each group comes up with a team name and then creates a team “crest” that best describes them, their name, and their motto. If you are outside, they can also create a “fort” using materials available (sticks, cardboard, leaves, etc).

  • What You Need:

    • For Crest: large white cardboard cutout, art supplies.

    • For Fort: Cardboard, tape, scissors, art supplies.

2. Beg, Barter, Solve

  • Timing: 20 minutes

  • How You Play: Each team gets a puzzle that has some of the pieces removed. The removed pieces are distributed across the other teams. The goal is to complete your own puzzle first, but you must figure out how to get pieces from the other teams, whether it be bartering, point transfers, mergers, etc.

  • What You Need: Puzzles! We used 45 piece puzzles and removed 9 pieces from each puzzle to distribute to the three other teams.

3. Zombie Battle

  • Timing: 10 minutes per round

  • How You Play: Teams stand across from each other in two lines. Individuals pair off with an opponent across from them. Once the game starts, pairs stare at each other with a zombie face—slack jaw, grunting, drooling, etc.—it’s all fair game. The first person to smile or laugh is out and their opponent finds another person to pair off with. Eventually there will only be two people squaring off, which will decide the winner.

  • What You Need: Nothing but a solid zombie impression.

4. Trivia (of course!)

  • Timing: 20 minutes

  • How You Play: Teams get together to answer a series of questions.

  • What You Need: Trivia questions. Make sure you add in some company trivia, too!

5. Food Fight Relay Race

  • Timing: 20 minutes. Depending on your timing, limit each section to a few team members instead of every team member.

  • How You Play:

    • Citrus/Skip/Pass

      • Selected team members must traverse a set distance while passing a grapefruit that is held by their chin. No hands! Each team member must accept the fruit and then skip to the next team member.

    • Cheez Balls & Shaving Cream

      • One team member is the receiver and one is the thrower. The receiver must cover their hands or face with shaving cream. The thrower then throws cheez balls at the receiver, trying to catch them in the shaving cream. If the receiver is using hands, they cannot grasp the cheez balls but can move their hands up and down.

    • Salty Telephone

      • Selected team members eat three saltines, standing in a row. A ref will then whisper a phrase to the first team member. That team member has to whisper the phrase to the next team member, so on and so forth until the final team member is able to repeat the phrase coherently back to the ref.  

    • Dizzy Watermelon Snacks

      • Selected team members run around a bat 5 times (with head on the bat). They then need to pick up a baby watermelon and run to their team. Once they reach their team, the team (and NOT the person that just ran around the bat) must cut the watermelon up into slices. The relay ends once the whole team has a piece in hand!

  • What You Need: In general: Plates, cones to block off distances. For each team: a grapefruit, bucket of cheez balls, 1 can of shaving cream, 1 box of saltines, a plastic bat, small watermelon, watermelon cutter (or knife).


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Regis Wakefield Headshot1

Regis Wakefield is the Operations Manager on the Employee Experience Team at Greenhouse. She spends her time finding new ways to make Greenhouse an awesome place to work, both in and out of the office. After hours, you can find her adventuring, baking (& eating) cookies, and co-leading the Greenhouse Space Club. Connect with Regis on Twitter and LinkedIn.

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