It was finally time for our first (annual) team retreat and I was pumped. Planning events like this get me excited: I wanted to be sure the whole team (then at a record of 13 people) not only had a restful and positive time, but also that we moved forward as a company— in both culture and strategy. No easy feat. In preparation, I did my Googling & Quora-ing, but wasn’t successful at finding things that had worked before for startups of our size (and not to mention with limited resources). So I started mostly from scratch— and, quite a few months after the terrific retreat, have finally found a chance to put everything I came up with and the best advice I heard together into useful tips so others can do it way more awesomely. Our itinerary is also included below. Hope it’s helpful!




Make Your Goals Really Clear

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 contain all of our cultural values; come up with an idea for a potentially viral landing page idea that’s fun and easy to execute; discuss and get on the same page in terms of our long 5-year vision; etc…

Find a Cheap-Ass Place & a Cheap-Ass 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. Use AirBnB (we did and found an amazing cozy home in Garrison, NY for an unbelievable price) and ZipCar (if someone already has an account), rent a car, or ideally you’ve got one already. A few members of the team even took the MetroNorth.

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 will work!

Sweat Together

For a health & 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 activity together every couple weeks (we call them “gractivities”). 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.

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 well! 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 & asked the leaders to come up with some sort of plan for it. We had all kinds of stuff: group meditation and arts ‘n crafts, baking competition 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.

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 together to begin with. Or haven’t really given each other a chance. I assigned pairs in advance for nearly every activity—and think it worked really, really well.

Cook 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 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 Super Stop ‘n Shop to purchase everything we needed (two HUGE grocery carts-worth) so we’d be ready. Cooking, eating, and cleaning up together is a magical thing. Don’t overlook 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 I’m not sorry).

Do a 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. Based on another brilliant idea from Andrew Heyward, I asked everyone to bring a personal item (could be an object or just a photo on their phone, so no stress) that shared something about who they are that most or all of us didn’t know already — something totally not work related. Over breakfast one morning, we went around in a circle and told our stories. It was super moving and one of my favorite moments of the entire retreat.

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

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. 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!


Preparation Beforehand:

-        Find a place and figure out transportation. Obviously.

-        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

-        Set up a cooking & cleaning Google Doc as well. Make sure there’s a column for a shopping list!

-        Finally, set up a vacation responder. Seriously. Here was ours: “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]!” I set vegas [at] to forward to my personal email in case of emergency.

Supplies Needed (other than food & drink):

-        TONS of markers & crayons.

-        Two Post-it Tabletop Easel Pads with Dry-Erase Board. I love these. We ended up un-sticking the sheets when working in pairs, then putting them up on the wall when presenting.

-        Lots of printer paper.

-        Equipment as-needed for any activities (interval training timer, e.g.).



Day 1 (Thursday Night):

Travel via car to the home in two separate rides, a few took the train.

We arrived & while some people familiarized themselves with the home, a few went shopping for food and drink supplies. All of the travel and shopping took far longer than anticipated, so people were super hungry (plan in advance!)— but everyone was in awesome spirits.

Chicken lettuce wraps for dinner.

Dinner announcement setting the expectations for the retreat. (See above!)

Short-term brainstorming. Had everyone split up into pairs, then draw on a big sheet of paper their ideas. This was hugely productive— each team presented, then we briefly discussed. Invigorating start to the trip and really put everyone in the right mindset, I think.


Day 2 (Friday):

Optional morning run.

Baked goods & fixin’s for breakfast.

Morning meditation.

Free time.

Burrito bowls for lunch.

“Think Wrong” brainstorm.

 “Martha Grewart” challenge (basically a baking competition).

Free time.

Veggie quinoa and chicken salad for dinner.

Community Contract creation. We shared the values we think are important to our community—and the habits that are important to each of us (from “wash your own dishes” to “overcommunication.”) We put that on the whiteboard and continued adding until we were all out.

Core Values Interview Questions. Taking Greatist’s Core Values, we worked together to come up with standard questions that answer each of them.

The “Newlywed Game” and drinks (lots of drinks). Finally, the leader of this activity had collected some funny but true answers to a set of questions in advance—and then put us all to the (hilarious) test.


Day 3 (Saturday):

Crispy potatoes with green beans for breakfast.

Show ‘n Tell with personal items. (See above!)

Epic team hike.

Roasted veggie quinoa + tofu and chicken for lunch.

Stress ball arts ‘n crafts.

Stage combat class. Hi-ya!

Interval/strength training class.

Viral landing page brainstorming in pairs + presentations. Some brilliant ideas, some hilarious ideas, and some ideas we’ve already put into action (see InstaMotivation).

Tofu + chicken sesame stir fry for dinner.

Long-term brainstorming. What do we want to be doing in 5 years? Split the group into two (because then, in smaller groups, everyone speaks and then their opinions have been validated/confirmed by someone else already before it turned to the larger group).

Drinks, s’mores (!!!), and more.


Day 4 (Sunday):

Optional yoga class.

Spinach + tomato egg bake for breakfast.

Discussion, “around the horn,” on why Greatist & why each team member is at Greatist. Inspired by the idea of cultivating “stories of self” from an Inc article that discusses the Obama campaign—we do this relatively informally, but never enough.

Then, after some tears (just kidding), everyone headed home.