Offsites#

I love remote work, but sometimes it sucks. Offsites can help.

Motivation#

Remote work empowers people to shape their work to fit their life. It also lets people focus on important work for long periods of time. Remote work is great for individual productivity, but makes iterating with colleagues expensive.

Slack and Zoom are useful for keeping up with colleagues, but not great at helping teams work through challenging problems, either technical or social. Over time remote teams accrue some alignment debt and interpersonal friction. Offsites are useful at rapidly paying down that debt, and aligning the team so that everyone can go off again and work remotely without expensive coordination.

The rest of this article discusses how I’ve been running offsites.

Small Groups#

I like groups of 5-10 people. Larger than that and logistics become hard, meetings become over-voiced, and people break up into cliques anyway.

Smaller groups can also assemble far more rapidly, allowing you to use offsites to handle emergent issues.

Ideally, offsites are also an opportunity to bring people together from different teams. I personally prefer mission-based offsites rather than team-based offsites.

Mission#

It’s useful for an offsite to have a specific goal that can be solved.

Ideally this is something that everyone present immediately recognizes as a pain in their side. This also has to be something that can be resolved either at the offsite or shortly after the offsite without requiring significant coordination. It’s powerful to have the group leave with a sense of accomplishment.

Even if the primary goal of the offsite is to align the team emotionally and reduce inter-personal friction I find that having a mission/goal is helpful.

Small Teams and Rapid Iteration#

When solving a difficult problem I expect to fail a few times. That’s ok, failing is good for learning, and once you’ve learned it’s often the case that you can find a 10x faster solution to the same problem.

Because of this, I tend to avoid pre-structured agendas and large team meetings. Those assume that I know what I’m doing, and I don’t. Instead, for me offsites are about getting a group of smart people to iterate quickly on a larger topic. Tactically, I do this with the following process:

  1. Get together as a large group for 20 minutes for a broad conversation

  2. Based on that conversation break up the group into smaller teams (or individuals) to work for a couple of hours on some component

  3. Congregate and share what happened. The team assesses the work, identifies issues, and then we redirect efforts

  4. Repeat at least twice a day

With a few teams and a few days this allows us to iterate through 10-20 stages of a larger objective during the offsite, which I’ve found has good success.

There are two anti-patterns that naturally evolve that we need to call out explicitly and work against

  1. Large group conversations during work periods

    People naturally congregate into larger and larger groups. They feel productive listening in on a large conversation, but this means that they’re only exploring one thread rather than several. I like letting these go on for a little bit (10-30 minutes) but then breaking people up again.

  2. Large multi-session efforts

    Often we find large and important problems and want to tackle them right away. However these problems can easily dominate part of the team for the entire offsite, and this work can often be done separately at home.

    Offsites are great to identify and align on larger work threads. Then when we go home we all know what we should work on independently.

Break#

It’s a normal workday. People should get in around 9-10am and be done around 5-6pm. Then they get to socialize more. It’s totally ok to not be working all the time. There’s a lot of value in all of the various breaks. I don’t think the offsite should be just about breaks / emotional bonding, but a healthy mix is good.

Buy nice food and beer and wine. Everything is free relative to employee time.

Beautiful Venue#

The team is undergoing hardship to travel to a remote location. It’s the company’s responsibility to provide a beautiful and engaging venue to compensate for the difficulty.

I prefer large organic spaces, like renting out a large house by a lake or ocean. This provides a more familial rather than professional ambiance, which I prefer.

Solicit Ideas Ahead of Time#

People will want to voice concerns that they have on a topic. Ideally they can voice these concerns asynchronously ahead of time, such as on a shared Google Document. This probably makes sense to send out a week ahead of time. Often people will forget about this document and so it’s important to trigger communication again before landing.

People need to voice their experiences and opinions. It’s better that they do so asynchronously (cheap) rather than in a large group in-person meeting (expensive). These are often important conversations, but they can dominate the entire offsite if there isn’t some work done ahead of time.

These ideas can also be sourced from the entire company, rather than just from the group that is attending. Ideally as much conversation happens on this doc as possible ahead of the event.

Schedule#

Typically people fly in one day, we have a dinner that day for people who arrive early enough. Then folks work for two full days, and then the following morning allowing people to fly off that afternoon (or stay the extra day in the beautiful location).

Invite Visitors#

Investors or collaborators in the area may want to join for a time. I’d encourage you to start the first day with just the team, but adding people over time can be energizing.