How We Designed Our First Groovy Gathering

Designing a team meetup to balance connection, inspiration, and focus.

The Groove Team. Virginia, 2022

The Groove team gathered for our first time all together in person the last week of November in the Blue Ridge Mountains of Virginia, where I’m based.

If you lead a small team or remote-first company, you may be asking yourself: When’s the right time to gather in person? Is it worth the time and resource investment?

We wanted to share our approach, which may help as you work through these questions.

(But before we begin, a special thank you to Peri Rothman, who pulled this whole event together in just three weeks!)

Why Meet IRL?

From its inception, Groove has been a remote-first team. And while that has a number of benefits, one of the main challenges any remote team faces is building a strong company culture.

We want our team to:

• Feel connected to one another, even as we work across time zones
• Feel a strong sense of alignment in our day-to-day work

While weekly team meetings, voice notes, emojis and gifs in Slack, and of course, Grooving together, add a sense of humanity to remote work, we knew that it was time to host our first Groove Gathering, to really create a strong sense of culture and connection.

When is a Good Time to Gather?

The best advice I got when I realized we needed a meaningful offsite came from one of our angel investors, who said ‘There’s never a good time for an offsite. And, it is still critical for you to make one happen.’

With that in mind, we picked a date, confirmed with the team, and jumped right into planning.

Our Gathering Design Approach

The first thing we did in designing our meetup was we asked our team “What would you like to come away from this gathering with?” It came down to a few core aspects:

1. First and foremost, the team just wanted to get to know each other better. They wanted to feel like there was more of a rapport that could be leveraged in the day to day.
2. They wanted to help understand Groove’s vision and goals.
3. They wanted to understand how their work as individuals fit into that vision.

It felt like the best way to answer these questions was to take the team on a journey that felt very Groove. One of our investors shared that the gathering should be an extension of our brand. Whatever you do, should feel like you. It shouldn’t be a cookie-cutter experience.

Our Groovy Gathering: A Playbook

Groove is driven by our values, our mission, a strong desire to see our impact in the world, and our love for a good time. So that shaped how we shaped the journey we wanted the team to go on.

The final schedule for our Groovy Gathering 🕺🏼

Each day of the gathering had a different theme that guided the day’s activities.

Day One: The Core of Groove. Value. Heart. Vision.

Morning Hike
We kicked things off with a morning hike. This was a chance to find a flow with each other in person. Taylor, our Head of Community, led a great exercise with the group: we divided into pairs and told one another the story of our lives in ten minutes our less.

Value Session with Tova, Co-Founder & Chief Design Officer
The core session of the day was discussing our own core values as individuals, then how we can bring those together to shape Groove’s values. In a growing team, values shape every decision whether explicit or implicit and we wanted to start to make the shared values more explicit for the team.

This was our process:

1. We each wrote down values on index cards that are important to the person.
2. Everyone told one story connected to a value that was most alive for them.

Then we shifted to collective values…

1. We clustered the values that came up often.
2. Then we were all given 10 votes to put on cards
3. We filtered down to 10 values (ended up being 11 — it was more about the process of becoming connected to shared values than a final set of shareable values)

Finally, we brought them to life with a vision board with magazines to cut up, stickers, paints, markets, and fabric.

Groove’s 4' x 4' vision board, built around the team’s values

Our own take on Fuckup Nights

Over dinner, we shared stories of some of our fuckups in life. It was a meaningful time to learn about each, be seen, share reflections, and laugh a bunch too.

Day Two: Where Are We Going?

This day was all about getting a shared sense of where do we need to be in a year from now to raise a Series A round and ownership of how are going to get there.

I kicked off the day with a session about how Series A investors think. We covered

• Basic Fund Mathematics (stolen from a session at Camp Resolute)
• What signals are investors looking for?
• The process of fundraising and what constitutes a good story
• In the current market am I hearing signals of where we need to be as a business to raise.
• Our Senior Ops, Joe, presented 3 scenarios of an operating model that could take us there.

We broke up into 3 teams (there’s 10 of us) with a pretty even split between engineering, growth and ops on each team. I then shared a slide deck based on Sequoia’s pitch deck outline as a prompt for the teams to develop pitches. The pitch exercise was assuming they were at investment committee with a series a fund, 12 months from now. They had to project what we had accomplished over the next 12 months and where we are going from there.

They were given 2 hours to develop a full pitch. An impossible task, seeing how the teams came together, and focused on areas they thought would be most important for investors, whether the story, traction, momentum was powerful.

Each team pitched after dinner in a light and casual way. Importantly though, people felt the size of the task at hand and it felt more possible than ever as each team mapped out how we could get there.

Afternoon interlude

My wife also led a session on how to build a fire outdoors (in the cold) with one match. Small groups tried to build a fire without success and then we learnt what the key to making a successful fire is. I mention this session not just because it was pretty cool that my wife was teaching the team how to build fires, but because it became a powerful metaphor for decision-making at an early-stage startup.

When you want to build a fire, there’s a useful framework of “breakfast, lunch and dinner” — you start with super small dry leaves or cardboard as the breakfast, letting that catch fire first. Once it’s strong enough, you add “lunch” — slightly larger kindling like think sticks. Once that’s going, you add “dessert” — big logs.

If you jump right into trying to light big logs, you’ll never get your fire started.

We kept referring to this framework when figuring out what we need to focus on first as we try to reach our goals and get the metaphorical Groove fire burning bright.

Dinner activity

Sruli led us in reading Dr Suess’ Oh, the Places You’ll Go over dinner. That book is jammed packed with insights, values and ways to relate to the journey of building a startup.

Day Three: What Does Groove Need to Win?

After getting everyone to think big about where we need to be in 12 months, Sruli, Co-Founder & Head of Product, led us in a UX research exercise to explore some core questions and turn our dreams of yesterday into reality.

We interviewed each other in pairs for 30 minutes on these 7 questions

1. What does it mean for Groove to win the next 6 months?
2. What needs to happen for Groove to win?
3. What is preventing us from winning?
4. What energizes you most about how we are going to win?
5. What would be a key metric that show we’re winning?
6. How could we accelerate winning?
7. Anything else you’d like to add?

These core questions were a gold mine for uncovering themes, challenges and opportunities for us.

We are big fans of post-its at Groove

Each team member wrapped up the session by sharing a few line mission statement capturing the important themes from the day.

The recurring themes from the sessions were:

1. Ruthless prioritization
2. Urgency
3. User acquisition strategy
4. Clear messaging
5. Experimentation
6. Persona
7. Team support each other
8. K-Factor (viral growth coefficient)

We ended the day with a dinner with local Groovers LaShonda and Moshe.

The Groove Team & Groovers

Day Four: How Do Teams and Individual Employees Win as Groove Wins?

We kicked off the day with some coworking time in Charlottesville.

After lunch we learned the basics of cultivating mushrooms and then spent the rest of the afternoon in an important closing workshop.

We gathered as teams to reflect on the themes from day three, discussing where we performed well and where we have been weaker. Teams regrouped with the outcomes of those discussions. Three major themes emerged from those discussion which formed our Q1 priorities

1. The whole company needs to take ownership of finding our market. Tightening the persona and carving a path to sustainable user acquisition.
2. Create better culture & structure for collaboration between product/engineer & growth teams
3. Increase predictability and transparency of timing of product releases by the engineering team.

How the Gathering Impacted the Team

It’s been just a week since we’ve all returned to our normal WFH lives, but we’ve already seen a massive increase in our team’s quality of communication. We were able to share ideas, create alignment and see different perspectives, by holding the space to get to know one another.

Without this gathering, I think it would have taken us much longer to arrive at the place we are now. We’ve accelerated the process of building our company culture and creating a collective vision towards Series A funding and Product-Market Fit.

We’re ending the year with energy, with clarity, trust, and conviction. We’re ending 2022 ready to tackle 2023. Here’s what the team has to say about their work after our Groovy Gathering:

“I’ve always worked on Groove because our mission of helping people design and live the lives they want is near to my heart. But now I’m really excited about how we can make this change at scale. During one of our sessions, Taylor and I imagined walking through Central Park on a summer day, and we saw everyone on a Groove or doing a Groove-based meetup. In that vision, people aren’t scrolling and consuming. They’re connecting, they’re living, they’re Grooving. That vision has me fired up.” -Ash, Marketing

“I feel very energized after the sessions. I definitely look at it more from the values perspective now, seeing how mission-driven everyone is. Before over-engineering things and before jumping into the implementation of features, I ask myself: ‘Does it contribute to increasing the number of users, and to improving the stickiness of the product?’ I’m going to keep shipping features. But I also wanna put more effort into thinking about ways to improve our metrics.” -Kamil, Product

What We Learned

We were really excited to host our first Groove Gathering, so there was a lot of pressure to make every moment count. Team members from Brazil, Canada, Israel, Poland, and the Northeastern US were all under one roof, so the stakes felt quite high. Moving forward, I think it’s important to lower those stakes as our Groove Gatherings become a regular part of our year.

My advice for other founders planning meetups for their teams:

1. Don’t try to do context switching too much. Try to get a flow (a creative flow, a coworking flow, a learning flow). Ride that wave.
2. Don’t be too serious. Be playful with the activities, it will allow everyone’s brain to engage with the activities in different ways, and that will translate into more creative work on the other side of the gathering.
3. Look for interesting Airbnbs, or other places that you can come together. Make sure there’s decent internet and an adequate space for gathering. That central space will become your home for the duration of your gathering. Make sure it has a unique energy in its own right.
4. Get your team involved at every level of the retreat. We’re not a big corporation, and we never want to be a big corporation. So it was all hands on deck, all day. The team put on their own bed linen, cooked together, cleaned up after meals together — those small actions were actually creating a foundation of teamwork and collaboration. It helped the team realize, through action, that we’re creating Groove together. This was a small, but unique opportunity for us, and should not be overlooked by other founders.

We’re energized more than ever to close out the year and kick off 2023 strong!

Have you hosted a team meetup? What did you learn from it? Does this resonate with you? I’d love to hear about your experience. I’m also happy to chat through anything we did in more detail if you are planning your own small team offsite.

Looking for more Groovy Content? Check these out:

1. Meet the Groove team
2. Authentic human connection powers our best work (and lives)
3. Or, start getting sh*t done the fun way at groove.ooo 🕺🏼