Designing a successful IRL meetup for a remote team

Automattic is a distributed company so we don’t get all that much time together.  This means that whenever we do I am always really mindful of how to make the most of it.

Team meetups are one such opportunity: we fly in from different parts of the world for a week or less to brainstorm, ship a project and connect. How does one design a successful meetup for a remote team?

I’ve led two, one of which was last month in Lisbon and while it’s fresh in my mind I decided to share a few ideas and learnings around how to make the most of IRL time together.

Start planning the agenda early

For both meetups I’ve led, I have felt enormous self-imposed pressure to make it productive, fun, a good use of company finance, the best week of people’s lives etc.

Honestly, it’s made me a little anxious!

Something that has helped allay my anxiety both times is planning out a detailed agenda and starting to do this quite early. I leave it open in a tab and it’s something of a work in progress that I chip away at and iterate on as I have ideas. When I think I’ve made headway I share it with my lead for input and then share it with my whole team so the planning is collaborative.

The other option is to plan it all out yourself, and perhaps that works for some people, but for me arriving on a meetup and embarking on a mission we have planned collaboratively (and is therefore owned by the whole team) is a lot nicer.

A full fridge saves time and money

Having a fully stocked fridge won’t guarantee you a successful meetup but it might help keep the budget on track and afford day-sleepers a little more shut-eye. Instead of everyone needing to trek out, breakfasts on our meetup were DIY at the AirBNB which meant a 9am sharp start was realistic each morning.

Scope out a grocery store near your accommodation before arrival and secure help to carry bags. I constantly re-learn the lesson of not being able to carry ten full bags at once.

Of course folks can (and should be encouraged to) buy their own snacks and expense them – but having a full fridge saves time and money and feels homely.

Kick-off with some positive individual feedback

Meetups for remote teams can feel kind of alien.

A collection of people accustomed to working solo and conversing asynchronously suddenly find themselves sitting around a table. This can be a little intimidating.

Warren, my lead, has always kicked off our meetups with some positive feedback for each person and I have adopted this ritual.

I write up something about each person, and read it aloud to them in front of the rest of the team. An honouring, encouraging starting point helps put everyone at ease, feel included and sets a good tone for the rest of the week.

Preparing this in advance is important – I don’t think doing it on the fly is wise – so that what you share is considered and meaningful.

Pick a deliverable project everyone can contribute to

My team is responsible for WooCommerce marketing operations and we’re a mixed bag of skills and foci.

Day to day we often end up working in parallel lines, or in huddles, or handing things over to one another in something of an assembly line. It’s rare that all of us work on something simultaneously (especially because we’re scattered from South Africa to London to San Francisco).

Meetups present a wonderful opportunity in this regard.

There is something about an all-hands-on-deck sprint when everyone is in the same room that builds morale uniquely.

For the two meetups I’ve led there has been an open floor in the lead up to suggest a project and the two we have chosen have been things we could all get stuck into:

In February when we met up in Barcelona we shipped the WooBookings Bundle including picking which products would be included, how to market them, creating the listing, creating supporting content, setting up ads and remarketing and communicating internally our plans for launch. This meant everyone in the (then) team could contribute.

For our meetup in Lisbon last month we responded to the call across our broader growth team to tackle ‘freemium conversions’ and spent our week shipping a number of email automations that we believe will drive the needle there. Kevin did a bunch of important ground work so by the time we arrived the research and scoping was complete.

The time we had IRL was spent divided into two teams tackling various chunks of the work – and by end of week we were able to put the automations live.

Choosing a project together with clear deliverables and then working hard alongside one another IRL to achieve them? The gold at the end of the team building rainbow.

Balance work and play

Being a bit of an A-type perfectionist the danger for me at a meetup is pushing everyone a bit too hard.

Doing work is good. But an equally important goal of meetups is the mystical bonding that happens while you’re kicking back and relaxing together (as much as I love bonding over work!).

In February when we had our meetup in Barcelona some of the feedback I got was that it had been a little exhausting. Second time around I made sure to plan in some more activities: mid-week we spent an afternoon and evening on a little coastal adventure with time on the beach and eating pizza overlooking the sea.

Balancing work and play on a meetup is important.

And beyond that making sure to understand and accommodate different idea of ‘play’ – because we all relax and connect in different ways.

Democratize meal and activity planning 

One way to ensure your meetup is inclusive and factor in different relaxation types is to democratize the planning.

As the lead you will probably need to do the boring things like budgeting and bills and bookings (all of the B’s) – but when it comes to meals and activities, get the team involved!

For both meetups I’ve led I’ve been lucky to have enthusiastic folk help out and share the load.

If there is someone who knows the city your meetup is in even better! Lean on them for local knowledge.

For our Lisbon meetup, Kat – who leads WooCommerce Documentation – was a star in helping us plan Lisbon dinners, lunches and outings. And Kevin, who had been there on a previous meetup, was also a source of good ideas and tips (although we never did make it to karaoke!).

Remember the introverts

Something I didn’t get right this meetup was planning in time to do: nothing.

I think we had a better balance of work and play this time around, but I didn’t include any time in the schedule which was for solo pottering, resting or snoozing. It’s not something I need, and it didn’t occur to me that others would.

So – when you’re structuring your week, remember to plan in some downtime.

Success will look different for every team

From what I can glean the two meetups I’ve led were mostly successful with some definite room for improvement in a few of the ways I have shared.

In closing: I think the surest way to ensure a successful meetup is deciding together what success looks like and setting your sights on that.

That’s it for my meetup learnings to date, I’m already looking forward to the next one!

#remote-work

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