Stepping out of the office for time with your team isn’t exactly a new concept. But when most of your team has never actually met ‘in real life,’ gathering in person has an added importance and function.

CloudPeeps is a distributed team with members in San Francisco, Brooklyn, Seattle, Orange County and Berlin. As a distributed team, we work closely together daily using tools like Slack, Google Apps, Hangouts, Asana, Trello, InVision, and Github. These tools have changed the nature of work, but there’s something special that happens when you’re face-to-face. So, we set ourselves the task of making the most of a team retreat with the added challenge of keeping it on a scrappy, early-stage startup budget – under $2,500.

How we planned

Our first actions were setting a date and picking a location. We polled for dates by asking each person to add their name to the best weekend in our team calendar. To optimize for budget and time, we focused on locations near where the majority of the team is based (San Francisco). Beyond accessibility, we wanted a destination that was beautiful, close to nature and inspirational. Lake Tahoe was an obvious first choice.

With a two-month preparation window, we started by nailing down accommodation, transport and activities. We stayed in this Airbnb cabin in South Lake Tahoe, and it was huge. We had five people attend the retreat (yes, we’re still a small crew) and there was plenty of space. In terms of the activity agenda – while we wanted to leave ample time for serendipity and ad hoc conversations, we did schedule out the three days. This allowed our team to know what to expect, plan personal time in between the team stuff and for us to make the most of our time on the ground in Tahoe.

What we did

In the spirit of full transparency and over-sharing, here’s our agenda:

Day 1

  • Morning: Attended a breakfast event where Kate was speaking about ‘Women & Powering Your Bottom Line
  • Afternoon: Drove to Tahoe and had lunch at a great organic cafe called Sprouts
  • Evening: Had a team dinner at cabin courtesy of Tessa’s top-notch BBQ skills!

Day 2

  • Morning: Hiked to Glacier Lake (photo below)
  • Afternoon: Lunched at Rojo’s and played mini golf at Magic Carpet Golf
  • Evening: Had a big picture strategy session over wine and pizza at the cabin

A photo posted by CloudPeeps (@cloudpeeps) on

Day 3

  • Morning: Hiked down to Lake Tahoe’s shore and Vikingsholm Castle
  • Afternoon: Visited Heavenly Village and had lunch at Latin Azul Kitchen
  • Evening: Continued the strategy overview over a simple dinner at the cabin

Day 4

  • Morning: Drove back to San Francisco, stopped off at Battery Spencer to take photos of the bridge
  • Afternoon: Had lunch at Cafe del Soul and coworked at Kate’s apartment

This @cloudpeeps crew in blue is truly awesome at what they do. #cpretreat #icanrhyme #sunnysf A photo posted by Kate Kendall (@katekendall) on

What we learned

Create space for conversations

For our inaugural retreat, we focused on connecting as a team and realigning our purpose. With a flexible schedule, we were able to recharge as well as have enriching team strategy conversations. However, in this effort, we missed the mark to allocate the space for one-on-one conversations. Many of the places we visited had picnic tables or open outdoor areas that would have worked well for this.

Set a clear tone and expectations upfront

We circulated an agenda prior to embarking on the retreat in order to set expectations and allow the team to start thinking of ideas and personal goals for the trip as they relate to the team. We did set some retreat goals, but clearer guidelines to set the tone, behavior, and actions required during retreat would have allowed us a more structured experience and outcomes. We suggest being ultra clear about time and how it will be spent to encourage pre-planning with reading lists, discussion points, outlines, etc.

Expect the unexpected

Two team members came down with a gastrointestinal bug which left them very unwell and unable to participate for a part of the retreat. We missed their involvement, but it was a lesson in keeping a flexible schedule. We were able to give them the space they needed to get better and create the headspace necessary to prepare for our strategy sessions once they were feeling better. In the end, it all worked out — the team was forced to rest and we all still had time to work together.

Mix it up

We found that mixing in strategy sessions between fun, outdoors activities worked very well. This allowed the team to get their creative juices flowing while getting to know each other better, opening up our lines of communication online in the long run. Even when partaking in fun activities, we would talk about work-related topics, but in a different tone and context, which resulted in different and creative ideas.

A long weekend isn’t enough

To build in sightseeing, coworking, team building and planning, four days felt a bit rushed. For the next retreat, we’d consider arrival on a Sunday with the team staying through the following weekend and inviting partners to come along from Friday night for a wrap up event.

And the budget?

Here’s the total costs

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