11 Tips To Make Your Team’s Next Startup Retreat Rock

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by Derek Flanzraich


When it was finally time for our first (annual) team retreat at Greatist, I was pumped. Planning events like this get me excited. I wanted to be sure the whole team (then at a record 13 people strong) not only had a restful and positive time, but also moved forward as a startup company, in both culture and strategy.


Turns out this is no easy feat.





In preparation, I did my Googling  and Quora-ing, but wasn’t successful at finding things that had worked when planning a startup retreat for a business of our size (and not to mention with limited resources). So I started mostly from scratch — and, quite a few months after that terrific retreat, have finally put together everything I came up with and the best advice I heard into a single set of useful tips — so others can do it way more awesomely, too.


How to Make Your Retreat or Off-Site a Success


1. Make your goals really clear from the start.

A friend and mentor of mine, Andrew Heyward, was an especially huge help in planning and thinking about the retreat. His biggest piece of advice was that the goal can’t just be “team bonding” because, well, team bonding is part of the journey, not the outcome.


Instead, focus on something really tangible and communicate that to your team. For example, ours included: create a community contract that contained all of our cultural values, come up with an idea for a potentially viral landing page idea that’s fun and easy to execute, and discuss our long five-year vision to get on the same page.


2. Find a cheap place and a cheap way of getting there.

If you don’t have the money, don’t spend it. The value of this isn’t a fancy-pantsy resort. Try using AirBnB (we did and found an amazing cozy home in Garrison, NY for an unbelievable price) and ZipCar (if someone already has an account), or rent a car, if you don’t have one available already. A few members of the team even took the MetroNorth Railroad.


3. Do an epic event of some sort that ends with a special view.

This seems obvious — but it’s easy to forget. We did an epic hike, but anything similar to that will work!


4. Sweat together.

For a health and wellness media startup like Greatist, it was obvious that fitness activities were going on the schedule. Outside of the retreat, we already do some sort of “greatist” activities together every couple weeks (we call them “greativities”).


On the retreat, we had an interval strength training workout, yoga class, and morning runs on the schedule — each led by someone different on the team. I’m always blown away by how effective sweating as a team can be in bringing everyone together.


5. Put every team member in charge of something.

You can’t plan and lead this all yourself, and you shouldn’t, either. The retreat should be as much a rest for you as everyone else on the team!


To turn our team members into retreat stakeholders, I had them each individually pitch a session to me and then put it on the calendar. Then, after some back-and-forth, I just added each of those sessions to the calendar and asked the leaders to come up with some sort of plan for it.


We had all kinds of stuff: group meditation, arts ‘n crafts, baking competitions and drinking games, a “think wrong” session, and even stage combat class (seriously). We used Google Docs to organize and manage everything, from assignments to hour-by-hour scheduling.


6. Utilize the power of pairs.

Two people are 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 big or small your company, people who don’t jive together often simply haven’t worked together to begin with — or haven’t really given each other a chance. I assigned pairs in advance for nearly every activity — and it worked really, really well.


7. Cook food that has substance.

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 made it a priority to plan each meal in advance, splitting into pairs for cooking and cleaning, and factoring prep time in advance.


We’re a health startup (and many of our members have food sensitivities: gluten-free, lactose-intolerant, etc.), so obviously, most of the meals were relatively healthy and simple. We even created a shopping list in advance and hit the grocery store to purchase everything we needed to be ready. Cooking, eating, and cleaning up together is a magical thing. Don’t overlook it or outsource it!





…but also have s’mores. This is my personal bias, but a retreat without s’mores is more like a lame-treat (sorry — OK, I’m not sorry).


8. Do a show-and-tell where people share something personal.

Based on another brilliant idea from Andrew Heyward, I asked everyone to bring a personal item (it could be an object or just a photo on their phone, so no stress) that shared something about who they are, that we didn’t know already — something totally not work related.


Over breakfast one morning, we went around in a circle and told our stories. Our team is made up of some truly special people, people who are very much more than just their job title. It was super moving and one of my favorite moments of the entire retreat.


9. Make sure there’s LOTS of free time.

It’s easy to over-schedule things (especially given how we treat our normal schedules), but don’t forget the importance of free time. People need their alone time (I know I do).


Your team will want to try something you didn’t expect was an option (a few of us spent roughly two hours chopping wood for fire with an axe, for example). They will need extra minutes getting ready or cleaning up. So factor free time in big time — make sure everyone has room to breathe.


10. Set the rules early, 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.


There was 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!


11. Finally, set up an email vacation responder.

Seriously. It will save you from having to worry about missing important emails, and stressing over not replying quickly enough.


Have you ever planned an off-site or team retreat for your startup employees before with success — especially on a limited budget? If so, I’d love to hear your tips!


A version of this post originally appeared on the author’s blog.


Derek Flanzraich is the founder and CEO of Greatist, a health and fitness media startup on a mission to make better choices easier for everyone. Also a fan of theme parks and theme bars.


Photo Credits

The YEC | Simon Howden | ponsuwan | FreeDigitalImages.net

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