For all my advocacy of remote and asynchronous work, I’m a big believer in getting together as a team as well. Working remotely and asynchronously requires a bedrock of trust. Otherwise, you walk on eggshells when you make decisions or communicate in writing. Your own intellectual guards are up and you make fundamental attribution errors when judging other people. As DHH says, you can’t have good faith on a flat social battery. 

I recently went out for a mid-week retreat with colleagues on my new team and as a fortuitous coincidence, I was one of the event hosts. The experience brought back into view a few of my principles and practices when organising such an event. In today’s post, I want to share these thoughts with you.

Interaction heavy, work light

In the last several months, as the return-to-office (RTO) clarion call has gotten louder, I’ve heard that people need to be in the same place so they can problem-solve and brainstorm. First, this is a collaboration superstition. Second, show me a team that needs a face-to-face (F2F) for brainstorming, and I’ll show you the missing facilitator. There’s very little work-related collaboration that you can’t do online. It’s tougher, however, to build relationships while working async-first.

I’ll be honest though. Organising a retreat is seemingly expensive, though often a trivial cost in the larger scheme of things. There’s always the pressure to “look productive” and engage in some productivity theatre if only for optics sake. I think this is a waste of time. Our team has 19 people in it. You can’t do any productive work that involves all 19 people simultaneously. Period. You must divide and conquer. And if dividing and conquering is necessary, you’ll do that much better online. 

I prefer keeping retreats such as these, interaction-heavy and work-light. Building camaraderie in the team is a laudable business outcome as well. In fact, in the last few years; ever since the pandemic; whenever I’ve met people in person, it’s been primarily a social interaction. Being intentional about these social interactions has helped me build more trusting relationships with certain co-workers. However, there are limits, particularly those of calendars and geography, that I can’t get around as an individual. This is where a sponsored retreat comes in handy. 

Avoid the dysfunctions

In my career, I’ve been to many F2F meetings. They were far more frequent in the years before the pandemic than they are now. These meetings suffered from several dysfunctions.

• Since they were infrequent, we’d invite as many people as possible to them. We know that it’s almost impossible to have a productive meeting with over eight people in it, and yet these meetings almost always had many more people in them.

• By inviting so many people, we raised the stakes of the meeting. So we’d pack the agenda to “make the most of everyone”. Before you knew it, the F2F ended up being back-to-back meetings in a meeting room.

• Even worse, we’d postpone things we could handle as small-group, ad hoc collaboration, to be part of the F2F agenda. After all, we were going to meet in person in just a few days!

I want you to reflect on the evolved dysfunction here. Many of these meetings used to be what we call, “offsites”. We’d take people out of the office for a change of scenery. But the packed agenda rendered going off-site pointless. Why go anywhere, if all you must do is sit in a conference room? So the off-site became “on site”. After a long day of meetings, people would meet for some gossip over dinner and hit the bed to crash. Did we get any closer as a team? I don’t think so. 

Keep things relaxed

Now, of course, if you get a bunch of people together, you must have a plan. I suggest, however, that you keep the plan light. Make time for people to relax, especially if they’ve had to travel a long way to get to the retreat. Things will go wrong, as they did during our retreat when a car broke down and some of us got to the off-site three hours late. When you ditch the packed agenda, you guard yourself against Murphy’s law. 

The relaxed agenda also gives people time to open up to each other and have meaningful conversations. For example, some of us took a walk in the woods to catch the sunrise by a lake when we were at our retreat. By the lake and on our walk, we had some memorable conversations that helped us understand each other’s worldviews. You can’t achieve this outcome in a structured meeting. Isn’t that worth something? 

We enjoyed a few relaxed meals in each other’s company. Breaking bread is among the most primal experiences of human existence. We’ve done it since the start of our evolution. Over these meals, we talked not just about work, but about our interests and life stories. Would you trade that for an anodyne working lunch? Or a rushed breakfast where you’re in a hurry to go to the next 19-person meeting?

Our team played a game together for a couple of hours. It was a mix of work and fun. The laughter and excitement in the room were palpable and culminated in uncorking the wine we’d brought along. How does that compare to death-by-PowerPoint in a boardroom? 

Some of you may say that all this is ALSO possible in addition to work-related meetings. I disagree. As human beings, we have limited energy. Saying yes to something also means saying no to something else. It’s very hard to spend a full day in meetings and then bring your most authentic self to a dinner by a bonfire. There’s also the limitation of time. Even with a relaxed schedule, some of us slept only by 11:30 at night. How do you reckon things would have worked, if we had meetings all day long?

Sweat the small stuff

Part of organising a retreat for a team of any size is to pay attention to tiny details. Some years back, I was part of a team organising a retreat for all my Indian colleagues. It was a large group - close to 1800 people if I remember correctly. In India, we don’t have hotels that can accommodate so many people, so some of our colleagues couldn’t stay at the primary location. We recognised this inconvenience. Just to show our appreciation and to acknowledge the people who were staying away from the retreat location, the entire organising team generated a bunch of handwritten notes. We paired these handwritten notes with tiny goodies that we left on everyone’s beds before they checked in. The gesture warmed everyone’s hearts. We needn’t have done it, but the attention to detail made a sub-optimal experience, a memorable one for many people.

The same attention to detail comes in handy even when organising retreats for smaller groups. For this recent retreat, one of us organisers baked some homemade cookies for everyone. I offered a pop-up photo booth for anyone who wanted a photograph for their social media handles. The local team members picked up the out-of-towners from the airport or the overnight hotel and drove them to the off-site location. By themselves, these little things cost little. But together, they add up to people’s memories and experiences of the meetup.

The cost of remote work

The biggest pitfall of remote work is to enjoy the apparent benefits, footing none of the costs. So yes, you can hire people and staff teams from anywhere. You can get away with smaller offices and reduce your operating costs. People don’t have to endure soul-crushing daily commutes, so they can be more productive at work. They’re also happier if they can stay in a quiet suburb or closer to family and friends. That affects retention and people’s sense of well-being. As an advocate of remote work, I could list out dozens of other benefits that ultimately affect your topline and bottom line. 

That said, it’s unwise to take all these efficiencies and redirect them to a fatter bottom line. Leaders must, amongst other things, think hard about how to make the remote working experience more productive, connected and engaging for their people. Intentional, regular team retreats are a business cost that distributed organisations must account for. 

At the risk of sounding like a broken record, let me repeat myself - these retreats shouldn’t be productivity theatre. Taking a couple of days away from deep work, to connect as a team doesn’t represent a loss of productive hours. When we were all back in the office, we weren’t 100% productive for 40 hours each week. We punctuated work with chatter, gossip, coffee breaks and indoor games. When all of that goes away in remote work, people inadvertently work their butts off for 40 hours each week. Sometimes more, because they don’t know what to do with the time they’ve earned back from not commuting. 

Most companies are saving on office space even if they’re not 100% remote. Plough some of your savings from office spaces into such retreats. The value you get from the resulting camaraderie will stand you in good stead, beyond your next quarterly report.

The OGs of remote work - GitLab, Doist, 37 Signals - don’t advocate for remote work as a purely cost-saving work pattern. Many of the benefits they aim for, several of which we address on this website, have nothing to do with cost. I’m no finance dude, so I don’t intend to preach advice beyond the skills I have. I can, however, do back-of-the-napkin arithmetic. Organising three or four retreats each year costs a fraction of what it takes to lease, build out and manage office space for the same number of people. The value you get from the recharged social batteries far outweighs the cost.