The Magic of the Off-site

Every tribe, be it a business, a networking group or a family, needs focused time together to set goals, reflect on mission and spend time just being together. It’s how we dial down the noise of the outside world and connect with what is most important. It’s where dreams find the freedom to grow into big, audacious ideas. It’s how we decide who—as a team—we want to be, and how we can reinforce our culture’s values in everyday practice. Ironically, as virtual as we have all become thanks to the wonders of LTE and autocorrect, the need for (and advantages of) face-to-face human connection seems bigger than ever.

Recently, a question around off-sites came up on our Founder platform, and it kicked off a great discussion of techniques, strategies and best practices from many of the companies in the True portfolio. I shared our strategy and commitment to regular off-sites in our own startup called True, and we decided to share those secrets and practices here as well.

Off-site meetings and retreats have been a critical part of True’s cultural fabric from day one. It was at Stinson Beach for our formation retreat where we set the enormously ambitious goal of realigning the entire venture industry to support and empower the creative Founder. That week, we codified a set of norms that we still enforce and honor today (no devices, straight-forward feedback to each other and to our Founders, and no jargon or buzzwords, to name a few). We also created our off-site schedule and strategy. Eight years into our journey, we have stuck to this plan and realized huge benefits.

The True Team meets for four one-day off-sites per year (quarterly) and one annual Stinson Beach retreat. The formats are different, as are the objectives. But the importance remains the same. We keep coming back because these events are our most cherished time together as a team and allow us to tap into a collective creative space. Here’s how it works:

Quarterly:

• We usually hold these locally, at an event space or hotel in San Francisco. We like Hotel Vitale a lot as they have some nice rooms with outside space, which allows for fresh air breaks during the day. The space needs to be large, open and clear of distractions. We like lots of light. We also usually have AV and some easels with markers.
• It’s important that the location is central so the travel time is minimized and the team time is maximized. Our team likes good food, so a hotel or location that can serve a good breakfast and lunch is essential (naturally, we bring our own Blue Bottle Coffee, and Tony dazzles us with his barista skills).
• Start time is usually around 9 a.m. and goes through dinner. We have lunch brought in and generally work through it.
• Dinner is at a different location, and we usually have that be more on the “fun” side, but the good thing is that topics often bleed over into our dinner discussion.
• Dinners are a great opportunity to celebrate the big or little things in our firm. I generally believe we all don’t celebrate and share our victories or milestones nearly enough, and often these dinners are a great time for these moments.
• We surface topics about 10 days in advance on our internal WordPress blog, then surface and sync first thing in the morning on the day of.
• Objectives of each quarterly off-site are threefold:
  • Strategy check-in: we discuss and question specific issues we’re facing strategically. Is the market the same now or are there changes, are our products still competitive, are there changes to be aware of or respond to? How are we executing in the current environment? Are any changes needed? What’s working and what’s not working?
  • Deeper dives: in our case, this means portfolio or reserve review, or specific company opportunities we want to discuss. Sometimes a specific trend in one of our home markets takes this section over (Bitcoin, devices and sensors, infrastructure).
  • Sync up on planning for the year: True University, Founder Camp, True Entrepreneur Corps and other programs and events. Are we on track, and who needs support in what areas? What do we do less of next year? What do we do more of?

Annual Retreat:

• We take 3-4 days and rent houses on Stinson Beach in the summer. It’s harder to plan and organize, and the travel is an issue, but it’s important for this one that we get away. Sometimes we cook and sometimes we have a caterer. We have found that cooking breakfasts and dinners together works well, but we usually work straight through lunch, so having that arranged is helpful.
• We work in the morning and play in the afternoon. We have BBQ dinners where we usually discuss some of the bigger topics, and then we enjoy good wine and catch up for the remainder of the night.
• The longer format enables much more open-ended conversation (i.e. over a couple of days and usually around bigger strategy stuff).
• We set aside some time to do the same deeper dives into our portfolio, products, etc. that we do quarterly. Every once in awhile we’ll invite up a few Founders who are in the midst of a very big decision. In the past, some of our biggest and best moves have been made up at Stinson (Fitbit, WordPress, Assistly).
• We try to focus our time at Stinson on “thinking big,” or at least “bigger.” Past topics have included expanding offices to NYC or Europe and adding new products that our Founders might need.
• We surface topics in advance, and start the retreat by surfacing topics. We’ve once or twice had specific themes or facilitated exercises (Enneagram training as an example) at this retreat.
• We always bring a professional photographer out for one of the days or evenings to capture our time together. While an expense, this has been incredibly important for our team’s sense of history and lore.

These off-sites have scaled over time from 6-8 people in the beginning to now over 20. We (usually) capture all the notes then post them up on our internal blog. We also try hard to stick to no devices/no interruptions/no other things for these days. Focusing on the focus is extremely hard, but incredibly important for any team.

The quarterly meetings are more of a grind and less fun, but we still enjoy our time together and get through a lot of topics. The Stinson retreat is something that we all cherish and really look forward to each year. Stinson has proven to be a sort of cultural touchstone for us, not so much because of the place, but more because of the tradition and the memories. We have made some momentous decisions there on the beach, and we all come to Stinson with big thoughts and big dreams.

One theme that carries through every single off-site is “there are no bad ideas.” In our culture, boldness is rewarded and vigorous debate is cherished. Failure and mistakes are essential to our success, so while we debrief and diagnose them, we don’t use this time for blame games or moping. Issues are identified, solutions determined, and then we commit.

We are lucky to have a crowd of people who go way back and are comfortable in their own skin. While some teams get lucky enough to start out this way, in all teams, and in our case, it’s this culture of regular time together that has made us a stronger tribe. It sounds simple, but it has helped us dream up new programs, events and platforms that we would never otherwise think of. The collective creativity of our team never ceases to inspire me, and the time we share in off-sites allows us to celebrate that magic again and again.

In his book “Subliminal,” Leonard Mlodinow points out that the brain processes roughly 11 million bits of observed sensory data every second of every situation we are in. Sadly, our conscious brain only has the capacity to process a tiny fraction of this amount each second (a few hundred bits). While the mystery of what we are actually doing with this subliminal data will persist for some time, there is no question that when together in the same room, we communicate more fully, more richly and with substantially more throughput than we can over devices or remotely. It’s my belief that teams who share time together, regularly, in shared space can get to big breakthroughs, solve enormous challenges, and create steadfast alignment, trust and even love. Our experience has led me to believe that there is much power behind face-to-face group interaction, and the off-site is an essential part of our team’s success.

So book that room, grab a shoe box for collecting all of the devices in the beginning of the meeting, stock up on BBC, and recommit to the possibilities and magic of the off-site.