I’ve run a distributed team — nominally the same team, though through people joining and leaving I am the sole original band member at this point — for almost 8 years. And about 3 years in was the first time we were sufficiently spread and had enough money to spare to warrant flying everyone to the same place for one week per year. We have been doing that ever since. Every year, it’s an exceedingly enlightening and pleasant experience.

And this year was the first time that we did not one but two team meetings back to back: first with my core team running education services at City Network, in the Hellerup neighborhood in Copenhagen, and then as part of the complete City Network all-hands meeting on the island of Tjärö in the Blekinge archipelago.

So here is how we do these things.

Accommodation

Except for the very first team meeting we did in 2014 when we put everyone up in hotel rooms, we’ve always rented a house. I’m a believer in small team sizes — 5 people being the maximum number of direct reports a leader can realistically have —, so that means that we can still find houses where everyone has a room to themselves, and nobody has to queue for a shower.

I consider both of these things extremely important. Many, many people working in tech are introverts, even more so for people working from home in tech. Many of us find the experience of constantly being around people emotionally draining, and we need solitude to recharge. Also, privacy. Our personal lives don’t stop while we’re having a team meeting, so you might want to have a room in which you can talk about your kid’s health issue with your spouse, without concern about colleagues overhearing the conversation.

Price-wise, since this puts us in an accommodation category that can qualify as a penthouse or mansion, this won’t be significantly cheaper than hotel accommodation — but it won’t be more expensive either, and it’ll be a much nicer experience. Particularly if you also have the joy of interacting with an exceedingly pleasant, nice, and helpful person for a host.

As for who scouts the accommodation, my rule has always been this:

  • In case we have a person on the team who lives, or has lived, in the city we’re going to, and who thus is very familiar with the locality and surroundings, I delegate the search to them. You can never beat local personal experience.

  • Otherwise, I do the scouting on the web, and I usually run it by the team — after I have made the booking, but while we can still cancel or change.

Arrival

Whoever did the scouting for the accommodation travels a day early, gets the key, settles in, and reports back. This has multiple purposes:

  • If they are local and so is the host, of course that’ll facilitate matters a lot. Particularly if we’re in a country where that one team member speaks the language, and the rest of us don’t.

  • If there’s something seriously wrong with the property, they can still cry foul and we can make other arrangements while we’re not all congregated in the same spot. (This has never happened to us, but just in case.)

  • That person is our support backstop who can field issues and customer questions, while everyone else is in the air.

  • That person can also meet and collect people at the airport or train station, if getting to our accommodation is nontrivial or difficult. Also, this is particularly helpful when we have a new team member who is perhaps less travel experienced.

First day

I normally don’t schedule any formal work sessions for the first day. People will be jet-lagged and fatigued from travel, we are often re-meeting in person for the first time in a year, and there is a lot of catching up to do about family, hobbies, recent travel, and all sorts of things that are not work. Somebody might be new and we might see them for the first time ever, in person.

And then of course people might be delayed in travel, may have had flights cancelled, or may have missed connections. So that means if you’re actually planning the first day to be full of “work” sessions, you ran a significant chance of your schedule getting wrecked by a flight delay. So we just don’t do that. Instead, we try to make the first day as relaxed and as enjoyable as possible, including a nice first group dinner.

And then sometimes, as happened this year, a remarkably serious and productive discussion over work issues ensues over a glass of wine in the evening. But that’s not part of the expectation.

Work sessions

We tend to have half-day work sessions these days, where we focus on one topic for 3-4 hours straight. These can get intense, and sometimes heated, but they are nearly always very, very productive.

We typically use a place like our house’s kitchen (if it’s roomy, and has a table), or patio (if it’s bearable outside), or sitting room (if it’s cozy) for work sessions. They are usually quite analog, with frequently just one person — the assigned record-keeper, often me — with a laptop open to take notes and record the discussion and its outcomes. I’ve found that on occasion, when discussing complex issues, working with a roll of brown paper and thick felt-tip markers (“sharpies” for you Americans out there) can be much more useful than with anything pushing bits.

Food

I enjoy food, and I’ve never worked with anyone who doesn’t. So we make that part enjoyable in whatever way we fancy. We might go for lunch to the neighborhood bagel store that our host recommended for their excellent pastrami. We might jump on a train to get to a street food spot, or head out for pizza or tacos or curry.

And I’m buying. These meetings are for work, my team is traveling for just that purpose, so whenever we eat together (and we practically always do), the tab is on me. What I can put on the company and what comes out of my own pocket is my job to sort out later, but we’re definitely not going Dutch.

Interesting things

Our meetings are usually in an interesting city with art, architecture, and history, and not seeing any of that would be a bit of a waste. So there’s usually maybe two to three things that we just go and do. It could be a harbor or river cruise, a visit to a castle or palace, a bicycle tour criss-crossing the city, or a museum visit. Depends a bit on the weather and a bit on individual interest.

Epilogue: going larger

So what works for a 5-person team clearly doesn’t work for a whole company, not least because you’ll be hard pressed to find a rental home with 40 bedrooms — I guess such a dwelling would be appropriately referred to as a palace, and last I checked the Queen wasn’t on Airbnb.

But you can take a page out of City Network’s playbook and do something else, which is to book an island. Yes, you read that right, immediately after our team meeting we packed up and boarded a train to join our company all-hands meeting, in which we had an island practically to ourselves.