How much work should you do on a team offsite?
The Tuscan village where remote-first company Doist is holding its 2023 team retreat

How much work should you do on a team offsite?

As the founder of a business that unapologetically champions the value of in-person human interactions, I spend a lot of time thinking about the best ways to run team and company away days.

From the off, I should explain that I’m not in favour of those that I would call ‘contrived’ away days. These are the familiar and well-trodden ‘stick-your-team-in-a-forest’ type of events, where these poor souls then have to build a bridge across a small river, or build a boat (or similar endeavour) to, for want of a better word, ‘bond’.

To me, these activities are simply not relatable to the world of work at all. Sure, you learn how to build a bridge, but how is that really going to help you work with someone to devise your marketing strategy for the coming year?

I recently read a blog by Chase Warrington , head of remote at Doist , which consists of 93 people representing 41 nationalities in 39 countries and 75 cities. The company works on a fully remote basis.

(Our team uses Todoist to manage our work - it's a great piece of software

Warrington describes how he’s been thinking about what he calls his IRL (In Real Life) strategy. In questioning the purpose of in-person gatherings, his philosophy is to prioritise what he calls ‘building social capital.’

For him this means “emphasising connection over productivity, building trust over building stuff,”; in other words, it means barely doing any work at all.

In a second post, Warrington expands on this thinking further, and even publishes the exact breakdown of the retreats he creates. For 50% of the time they comprise ‘free-time’; for 30% of the time, there are activities [social activities, not raft-building ones], with just 20% left for doing work [brainstorming sessions, presentations by the CEO, hackathons etc..].

I say ‘just’ for a reason.

While I admit that I don’t have all the answers myself, my gut feeling is that this sounds like a lot of time being spent as tourists (the all-expenses foreign-trip events cost $350,000 annually for the 100-plus staff that go on them).

This could seem more like a group holiday, with time spent visiting museums and doing other touristy stuff like that.

Don’t get me wrong. I understand the importance of building relationships, and creating psychological safety and trust, but this 20/30/50 ratio allows for only a few sessions devoted to talking about work.

Warrington argues that his way “maximises the return on our in-person time together,” by creating “a better understanding of your coworkers, and long-lasting friendships are formed, which we can lean on as a business for many months and years to come.”

But I still think that, at the end of the day, these sorts of events need to weave a sizeable chunk of ‘work’ into them. I wonder whether instead of the tourism, there could be more purposeful ways to integrate work – in a way that this also translates back the business.

Warrington says he “didn’t want to simply replicate what takes place in an office,” and I agree - there would be no point travelling to a different location together and then sitting writing emails and Slack chats and having recurring meetings.

Should these gatherings have more of a specific purpose – be it a business problem that needs to be solved, or another type of problem that needs to be wrestled with. For instance more time spent in workshop-style activities could help teams focus with intent on their key priorities and brainstorm new solutions, with the in-person aspect bringing a higher quality to their interactions and ideas.

I can't help but think that a more curated approach needs to be taken, and there's a risk the ‘tourist’ strategy leaves too much to chance.

Or, by empowering and trusting team members in this way, will it naturally work out that the topics that need to be discussed, get discussed?

I don’t know if I’m right; I don’t know if Warrington is right; and I do wonder if there’s a happy medium between the two.

What I do know, however, is that in-person team events (particularly as we become more remote) will need a much more thoughtful approach in the future.

I’d be interested to hear your views.

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