thederek

So there’s no playbook for planning a startup team retreat or offsite. And despite heavy Googling and Quora-ing, I still haven’t found anyone sharing what’s worked for startups our size (15ish people) nor with our limited resources (total budget = as little as possible).

But the good news is I’ve now lead two overnight and a handful of day-long team retreats at my startup and it’s seems like we’re starting to figure things out a bit. The intention to make each one better than the last, along with the enthusiasm and ideas of terrific team, means we’ve managed to pull off one after another successful retreats (we call them “gretreats” because of the company name, Greatist) or at least that’s what we think! The purpose of this post is to share the best what I’ve learned—the best advice and activities—so your startup’s retreats start even better than mine did. Hope it’s helpful!

Advice

Set Specific Goals

A team retreat can’t be simply about “team bonding.” Because that’s not goal, it’s a part of the journey. So what are you really trying to accomplish? What’s “success” mean for this particular team retreat? On our first overnight retreat, one goal was to create a community contract that contained all our cultural values. On our most recent retreat, one goal was to get the team completely aligned in terms of the priorities for the in quarter ahead. Another was to walk the team through a “necessary strengths” and “tolerable weaknesses” hiring exercise, then make it our own. This was inspired by a mentor of mine, Andrew Heyward, and his advice to focus on something tangible and communicate that to the team was so right on. The clearer success is defined, the more likely the retreat will truly move the team forward.

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2 - Find a Special Place and a Cheap Way to Get There

If you don’t have the money, don’t spend it. Our first time around we used AirBnB to rent an amazing cozy home in Garrison, NY for a terrific price. This past retreat we managed to finagle our way into the unbelievable New Life Hiking Spa in Killington, VT, which has basically taken over an empty Ski hotel in Vermont and created wellness-based programming, food, treatments, and festivities on top. It was a dream. For our day-long retreats, we’ve managed to rent out big rooms at far-away hotels and public parks. We’ve taken public transportation, rented cars, or even borrowed them. Every time we’ve planned something special without shelling out crazy amounts of cash. A memorable getaway doesn’t have to drain the budget—show your team genuine care through planning, not spending.

3 - Prepare Right

Planning? Get serious about it! We set up a master Google Doc and start putting all information and scheduling in there. Fill it in completely, hour by hour, assignment by assignment, drinking game by drinking game. The more comprehensive the doc, the less you leave to happenstance and the more you can simply enjoy the trip along with everyone (not easy to do when you’re scrambling to remember what’s next). We work with the team to create it (often asking different team members to lead an activity themselves) and then print it out beforehand for everyone to know exactly what’s going on.

Also, set up a fun vacation responder. Seriously. Here was ours from last year:

Hey friend, thanks for the email! I’ll be away from my inbox for a few days — Greatist is headed to Vegas (er, a small town in upstate NY called Garrison) for our first annual team retreat! We do our best to live the life we champion, and that means taking a few days offline once in a while. If you absolutely need to get in touch (like, really really need to) before Monday 9/24, email vegas [at] greatist.com!

I set vegas [at] greatist.com to forward to my personal email in case of emergency.

4 - Don’t Forget to Include LOTS of Free Time

That said, it’s easy to over-schedule things (especially given how we treat our normal schedules) so don’t forget the importance of free time! People need their alone time (I know I do). People will want to try something you didn’t expect was an option out (a few of us once spent roughly two hours chopping wood for fire with an axe, for example). People will need extra time getting ready or cleaning up. So factor free time in big time—make sure everyone has room to breathe and then some.

5 - Establish Expectations, Especially in Regards to Cell Phone Use

At our first dinner, I made an announcement about how I wanted this to go. Though we had a pretty set schedule, I emphasized that this retreat was about relaxation, unplugging, and enjoying ourselves. No rush to stick to the schedule—everything would work out. And that cell phone use, for the most part, was frowned upon—especially during any sessions (though outside of the sessions everyone was obviously free to use it.) I also made clear that I wouldn’t be doing any work—so no work was expected from them, either!

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6 - Power of Pairs

Two people is the perfect size for cooking/cleaning/shopping groups. It’s also perfect for brainstorming and presenting. A partner provides drive, feedback, and confidence. And it doesn’t hurt to think about assigning “strange bedfellows” together. No matter how or small your company, people who don’t really jive together often simply haven’t worked all that much together to begin with. Or haven’t really given each other a chance. I assigned pairs (or groups of three) in advance for nearly every activity—and think it worked really, really well.

7 - Cook/Eat Real Food

Don’t just order in pizza or Chinese. The food your team eats has a big impact on how they feel and act—and so we either plan each meal in advance (preparing, cooking, and cleaning ourselves) or emphasize the importance of healthier options wherever we go. We’re a health-minded startup, so it’s probably not surprising that many of our team members have food sensitivities: gluten-free, lactose-intolerant, vegan, etc… and that we tend to look for meals that are healthy and simple. If there’s a kitchen, we create a shopping list in advance and purchase everything we needed in bulk. If there isn’t, we coordinate food options beforehand. That doesn’t mean we suffer. Just the opposite! It means bringing the right kind of snacks, sneaking in some s’mores (this may be my personal bias, but a retreat without s’mores is more like a lame-treat—yeah, I said it.), and indulging in New Life Hiking Spa’s epic banana puree sundae.

8 - Show ‘n Tell in which People Share Something Personal

Our team is made up of some truly special people, people who are very much more than just their job title. For overnight retreats, I ask everyone to bring a personal item (could be an object or just a photo on their phone, so no stress) that helps them share a story about who they are that most or all of us don’t know already—ideally something totally not work related. We go around in a circle and tell our stories and each time it’s emotional and moving. It can be big or small, from a family member’s art that’s important to you or a funny tradition your childhood friends still share, but it brings people close together through sharing authenticity and vulnerability. It’s always among my most memorable moments.

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Activities

We’re constantly tweaking the activities we end up doing throughout the retreats and we actually gather feedback on every activity post-retreat and use that to inform what we do next time. We also always mix things up, trying new things on top of what have become classics that the team looks forward to. Here are some of my favorites:

1 - Viral Landing Page Brainstorm

The best way to get the creative, collaborative juices flowing is to just start. So we split into small groups, charged with coming up with a fun, simple landing page that we could launch. Then each group presents it to the team. It’s quick and effective and really put everyone in the right mindset, I think. And we take the ideas seriously, too! One popular landing page we created called InstaMotivation came straight from this exercise and now it even sits prominently on our homepage.

2 - Fictitious Competitor Exercise

Another interesting activity to get people thinking is one we call the Fictitious Competitor Exercise. I come up with three fake but plausible “competitors” (and write a paragraph about their strategy/approach) in advance, then assign each to a different group. Each group works to create an action plan for how to respond and then presents to the team as a whole. Of course, there aren’t any wrong or right answers with this—and in many ways it’s just an activity to clearly communicate how our company is already different, but the “reaction” is always illuminating and fun to think about.

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3 - Quarterly Priorities & Goals

Probably the most important activity we do now, the Quarterly Priorities & Goals is an exercise we’ve developed to address goal-setting as a team, making sure everyone is aligned and aware in terms of what the next three months will bring. We do this really differently than most and it’s evolved quite a bit over time, but it ultimately started from an exercise I did once with the very awesome BJ Fogg for deciding which new behaviors to pursue. What we do is give out lots of post-its to everyone, then for 10 minutes have them all write down what they believe the priorities should be and then stick those big sheets of paper for each of our departments (creative, tech, etc…). Then, each department meets and talks through which 3-4 to continue on, led by the department head. Finally, we create a big wall-size X/Y graph of “Impact” versus “Feasibility” and go one-by-one putting post-its on there. We go through in order until everyone is more or less satisfied with the results, have some chances to appeal and debate why something needs to be moved (but at this point a change needs a majority vote), and then finally come out with a  stacked list of team priorities. We also look back on how those priorities have shifted from the last retreat and whether we made good on the priorities we intended to follow-through on and why we did/didn’t. It’s a powerful, important exercise that keeps us all on the same page. It isn’t perfect (and every time we tweak/improve it), but it’s a start!

4 - Draw Your Job

A really interest exercise we started doing is called Draw Your Job and, well, it’s pretty self-explanatory. We pass out blank sheets of paper and give 5-10 minutes to each person, then ask them to draw their job! Afterwards, they present what they came up with to everyone on the team. The goal ultimately is to learn more about each team member’s role at Greatist, but also to learn what take’s up their time, pick up on common frustrations, and see trends in what makes everyone happy and excited at work. It’s a fun and surprisingly uplifting (usually hilarious) activity, especially for people who say they’re bad at drawing.

5 - Stories of Self

Inspired by the idea of cultivating “stories of self” from an Inc article that discusses the Obama campaign, this activity involves everyone taking some time to write (1) why they’re at Greatist and (2) why what Greatist is doing is important to them. Then we go “around the horn” and share. It’s a poignant activity to do when a retreat is wrapping up and often ends with a few tears, but it’s well worth it.

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6 - Newlywed Game

On the lighter side, every overnight retreat we do an activity inspired by The “Newlywed Game” where the leader (not the CEO) collects some funny but true answers to a set of questions in advance from the team (usually an online survey, basically), picks out their favorites, and then puts everyone else to the test (for example, “Who on the team has the most tattoos?” or “Whose worst date ever involved an accidentally stolen car and Red Vines?”). We obviously do this over drinks, sometimes lots of drinks.

7 - Try Something New

Doing the same activities over and over again is boring, so we always add a couple new ones to the schedule. Sometimes these are inspired by new team members and, at other times, they stem from a team need (for example the hiring exercise I mentioned beforehand). Don’t be scared to try crazy stuff—just communicate this is something new to everyone and let them feel it out with you. A recent hit like this was what we call “The Song Game,” where there are two teams and each person has to say a word that the other team has to remember in a song lyric somewhere, then sing it. It’s harder than it sounds! We basically modified something we saw online, then tweaked the rules even more as we went, and landing on one of the most fun exercises we’ve done yet.

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8 - Do an Epic Event of Some Sort That Ends with a Special View

Finally, do a big event that ends with a special view or celebration. It can become the crowning moment of a retreat—and is always worth the time commitment. We’ve done epic hikes, but anything will work! For a health startup like Greatist, it’s maybe more obvious that fitness activities would go on the schedule but, in my experience it’s amazing how effectively sweating as a team can bring everyone together. On retreats, we typically have some kind of workout, morning run, and even yoga class on the schedule (led by either experienced, passionate people on the team or similarly passionate professionals). At New Life this past June, we went on a very special instructor-led 5 mile hike with an amazing view, then (in typical #imagreatist fashion) ate local ice cream afterwards in the cute 18th century town of Woodstock, VT.

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I wish I had known not to get caught up in “the way things are done.” One of the big benefits of starting a new company is being forced to do things with limited resources and knowledge because there aren’t any other options. Because you simply don’t know, you often come up with better, faster, simpler solutions. However, it’s easy even for entrepreneurs to get caught up in the way things are done eventually. I know I sure have. Just like investors are often driven by pattern recognition, founders too look to what other successful companies have done to succeed or look to their competitors to see what they’re doing more and try to mimic them.
Among many things [a mentor] has taught me are five rules for happiness. So the first one is living in the moment. The second is that it’s better to be loving than to be right, and if you’re in a relationship, you know how challenging that can be. The third one is to be a spectator to your own thoughts, especially when you become emotional, which is almost impossible to do. The fourth is to be grateful for at least one thing every day, and the last is to help others every chance you get.