May 17, 2023

Retreats for remote teams

Having run 2 remote companies, I’ve found regular in-person get-togethers help remote teams work well. But they weren’t easy to get right.

At first, they were tweaked for productivity, but over time, I found focusing on them as a unique space for relationships to grow makes productivity take care of itself.

Even the least “worky” retreats easily pay off when compared to salaries. Two $10,000 retreats for a team of 5 who get paid $500,000 per year is a 4% cost, but easily makes the team 50+% more effective, just through the empathy and camaraderie that builds up..

What have by now been broadly labelled as “retreats” can be setup for a range of goals, from getting to know each other personally in a relaxed space, to planning projects, to co-working and getting things done. But trying to do all of those at once leads to unmet expectations.

Here are the 3 main retreat formats I found that work well, all with specific purposes.

The partners getaway (3 days)

At Founder Centric (four partners + 2 employees), we’d all go somewhere isolated and chill for 3 days, every 3 months.

Purpose: just to catch up as friends, hear about life, and to talk about how FC work fit our lives.

Rules: The main rule was no outside commitments, and no doing work, but talking about work is okay.

We’d leave with greater empathy about each others’ goals, life (including “lifestyle constraints”) and a few clear decisions about how we’d iterate our collaboration practices. (This lead to specific practices we’d want to try for the next quarter, see Remote Squads as an illustration) Generally there was no agenda, just nice dinners and hikes together, but we were expected to use this time to focus on each other.

We learned this needed to be a place away from home for everyone, but cheap and cheerful was really fun.

The Open Space unconference (1-3 days)

Source was much larger and amorphous, with ~30 on-and-off freelance team members. We ran a 10-20 person unconference for 2-3 days, roughly twice per year.

Purpose: This helped us sharpen our axes, but also brought us closer together in terms of working norms, because it enabled us to constantly experiment and share techniques.

The Source team could invite a few people each, and we’d have a combination of structured schedule where participants could propose skills-sharing, problem-solving or co-creation related to peer learning, and a few easily accessible group activities like castle visits, golf, spas, hikes, beach stuff.

We learned we shouldn’t invite anyone who was a client, potential client or basically someone we might feel inclined to impress. That shifted us from honest experience sharing to selling.

The prep week (4-5 days)

Purpose: The prep weeks were 2-3 weeks before the start of an educational program we were running.. When the actual program started, we’d be fresh, rested and confident. So investing a week together a few weeks prior was well worth it. Being together also remove a lot of back-and-forth questions, since our peer learning programs were highly interlinked.

We’d rent a big house somewhere for a week, and each day would have two 2.5 hour sessions for preparing some part of it, combining content, research, ops. The prep weeks would start with reviews of previous retrospectives, so we’d design the upcoming program with all of the previous lessons learned in mind (a great way to avoid carrying the same mistakes from iteration to iteration).

All in all, we’d do about 6 hours of focused work per day, so still have time to have chilled out breakfasts and dinners together, time by the pool or in nature, a few movie nights.

One of the tough parts here was because everyone had different projects (most of our facilitators were active tech entrepreneurs) it was important to schedule the same 2 hours per day for outside work. That way we could take care of those things but not miss the chance to spend time with each other.)

Where and when is a critical decision

A few useful tools for finding good meeting points:

A few factors to consider:

  • It has to be “away” enough for everybody so everyone is psychologically away their normal environment, and no one person gets obligated as the defacto host because they’re “the local”
  • We have to be fresh and in good spirits, so jetlag and multi-leg travel should be minimised. If your team is widely-distributed, invite the most jetlagged travelers to arrive a day or so earlier so they can relax and be fresh when everyone starts.
  • Also pay attention to accommodation costs (which can offset flight savings)
  • Driving time from the airport, and how people arriving at different times will get to the location

Trying to schedule a retreat around another event like a client project or conference is a recipe for cancellations and last-minute changes. It also communicates to everyone that the real goal of the trip isn’t for each other, but rather something else. Make the retreat 100% focused on the team by making the travel 100% about your teammates.

Finally, the biggest success factor I’ve found is to simply focus on creature comforts. Good food, good beds, natural light, nature and a range of physical activities set everyone up well. You can trust that people will do what’s needed to achieve the collective goal of the retreat without much structure.

The most critical factors I’ve found are: to have pre-agreed the purpose of the retreat, and to get everyone somewhere neutral and comfortable.

What am I up to these days?

I’m a new parent, and prioritising my attention on our new rhythms as a family. I’m also having fun with slow creative pursuits: making a few apps, writing, etc.

Work-wise, I’m trekking along at a cozy pace, with a few non-exec, advisory roles for cryptography and microchip manufacturing programs.

In the past, I've designed peer-learning programs for Oxford, UCL, Techstars, Microsoft Ventures, The Royal Academy Of Engineering, and Kernel, careering from startups to humanitech and engineering. I also played a role in starting the Lean Startup methodology, and the European startup ecosystem. You can read about this here.

Contact me

Books & collected practices

  • Peer Learning Is - a broad look at peer learning around the world, and how to design peer learning to outperform traditional education
  • Mentor Impact - researched the practices used by the startup mentors that really make a difference
  • DAOistry - practices and mindsets that work in blockchain communities
  • Decision Hacks - early-stage startup decisions distilled
  • Source Institute - skunkworks I founded with open peer learning formats and ops guides, and our internal guide on decentralised teams