pumpspotting is an MVF portfolio company which successfully designed and conducted their own corporate retreat to foster connection, creativity and cohesiveness. Given the nearly ubiquitous challenge of staying aligned and motivated in this digital age, we thought our readers would benefit from CEO Amy Van Haren’s story, which she skillfully captured below. Thanks Amy! 

How to Design an Impactful In-Person Retreat (And Why it Matters More Than Ever)

8 takeaways from the power of a well-crafted team retreat

As so many of us founders know, maintaining the strength and health of our teams is perhaps the single most important task. It drives everything from revenue to growth to living out our audacious missions, so it’s vital that our teams stay connected, aligned, and energized by the collective. Yet in this world of remote work and what can seem like ever-shifting challenges that connection can be vulnerable, fractured, hard to maintain.

I noticed those latter themes with our own team here at pumpspotting at the end of last year. We added new members, accomplished big wins, and found ourselves facing key milestones. We were achieving, yet it felt like we were operating in different keys. We needed something to bring us together; to remove the distance and restart our engines.

We needed a team retreat. A place to be together in person, to disconnect, dream big, and celebrate our wins. I could have booked us an event space, with hotel rooms and whiteboard walls, but chose instead to put energy into creating a unique experience based upon who we are as a company, and it made all the difference.

We shut down the day-to-day work for three days and headed to a big ‘ole Farmhouse in Maine with stunning sunsets, space to walk in nature, a kitchen to cook together in and sheep—yes sheep—to say hello to. While taking us out of the work, and our heads, for those three days seemed like a great ask of team time and budget, what transpired was transformative. It was the best investment I’d made all year.

Our retreat:

– Strengthened bonds (cross-connection vs silos)

– Fostered real relationships and allowed us to get to know one another as humans

– Brought a fiery return to the mission and re energized our focus on the work

– Set the stage for our culture and creativity

– Allowed everyone to be seen and share value

– Bolstered me as a founder and leader

Prioritizing time in person is more important than ever before. So is setting the stage for the time together in the right way. There is no one way to retreat but to me, mindfully shaping the experience makes for all the magic. 

Here are my best tips for designing a team retreat that delivers real impact and connection:

1. Set the tone by your company culture.

Show up on site the way you want everyone to show up in your day-to-day work. Use your culture as the theme and bring it to life. Our mission is to connect and nourish parents so we built connection and nourishment into every detail: Flowers in pump bottles, a team-curated Spotify list, colored pens in every size weight per team preference. No detail was too small from the warm beanies swag to the delicious and dietary-friendly food to giving the room with the comfy chair to the team member who would have to pump three times a day.

The more we considered the small ways we could bake our culture of connection and nourishment into every element of the plans, the more the team settled into the sense of what we are about.

2. Don’t be afraid to gather in.

Yes, I made everyone move into a farmhouse in Maine!

No it’s not the norm, and there was some initial uncertainty but here’s where the magic comes in: when you are physically all together for an extended period of time in one space, there is space for the small connections. The side conversations. The last drink before turning in or the first cup of coffee over the sunrise. You’re saying: “we are here as a team, and it’s not about work and retiring to your rooms, but rather work and exist as you are.” It sets the stage for work and real life to exist together always at your company.

3. Create space for connection (and keep it separate from the work).

Do come with a set intention and a clearly defined agenda. Section out each day and give it a goal or a purpose. Start with connection, end with intention setting, and sandwich the deep work in between. With clear delineation between when we worked on the business, when we were dreaming, and when we were strengthening relationships we accomplished much more.

I highly recommend Dave Bailey, The Founder Coach’s great insights on designing an effective strategy offsite and why it’s important to allow separate time for divergent (new ideas and possibilities) and convergent (analysis and decision making) thinking.

4. Don’t try to do too much. 

Make time to pet the sheep. Allow people to walk and reset. Put up a big piece of white paper for the parking lot and put MANY things there for next time. Also pay attention to the energy of the group and adjust for more space when it’s needed.

5. Give everyone the floor.

One of the best things we did was invite every team member to lead a :30 session based on their focus, obstacles, and wins over the past year.

This brilliant idea came from Leila Zayed, our VP of sales, and it had three powerful results: it allowed each person to be seen and valued for their contributions, it created amazing bonds across the entire group that have strengthened the collaborative work to this day (sales and lactation and product now help us build as one), and it gave us some great laughs. The varied presentation styles brought out the unique personality of every person on the team.

6. Celebrate strengths.

This is a time to put the teams’ individual and collective strengths on display. We did it formally, kicking off the event the first evening by sharing our Clifton Strengths and discussing each persons’ bring value to the whole group. We also recognized and rewarded them all weekend by wearing our strengths as stickers and yelling “donut!” every time we recognized Clifton superpowers coming to life.

And we did it informally, by organically celebrating people’s life strengths: margarita making skills, coffee curating chops, table setting flair, karaoke. (Just kidding that was the one thing everyone said don’t make me do on the pre-event survey!)

7. Bring it back to the day-to-day.

Make sure to make time to reflect on the experience together and call out what you’re taking back into the day-to-day work. Recommit to goals, both as a company and personally, and put them where the team can return to them to hold one another accountable throughout the year. Find ways to make the experience live on. (We still honor and call out our clifton strengths with a slack channel we call #donuts.)

8. Repeat!

We’ve planned for day-long quarterly reconnects and already have our sites set on our next annual experience. I’m not sure how I’ll top the sheep and sunsets, but I know we’ll all be fired up to gather in and connect, nourish, and crush it once more.

Amy VanHaren is a Mainer, mother, experience designer and the CEO and Founder of pumpspotting, a baby-feeding support solution making the world more inclusive for families.