Recap: Castos 2023 Team Retreat

I’m sitting in the Athens airport heading home from our 2023 team retreat.

To be honest there are a lot of emotions going on inside me right now. I’m all at the same time: grateful, happy, excited, proud, and scared.

To quote Ron from Harry Potter:

One person can’t feel all that at once, they’d explode.

Ron Weasley

Well, I haven’t exploded yet, but it’s a lot.

But, to keep this productive, I want to reflect on our 2nd team retreat in 2 years, and the things we’ve learned along the way. Hoping this helps you plan a more successful remote team retreat for your company.

Where

We chose Athens, Greece for our team retreat this year. Last year we were in Chicago, IL, USA, and it was great too. But honestly, Greece is amazing.

We chose Athens because WordCamp Europe is here this week. WordCamp Europe is the largest WordPress conference of the year, and with our deep ties in Open Source and the WordPress community, we wanted to attend this year.

Athens as a location was great. The weather was picture-perfect all week.

We’ve done a few different things with accommodations throughout the years with our 3 total retreats, and this year we stuck with a hotel setup. Same as Chicago last year.

We like that everyone is in one place, but everyone has their own separate (private) area. This is as opposed to renting a large AirBNB or something similar where we’d literally be living together.

Our hotel was right in the middle of the tourist area; an intentional choice on our team. I proposed a few options, and the team voted for where they wanted to stay.

Overall I’d say this was the one slightly weak part of the trip. The hotel was good but not great, and being right in the tourist area was good for part of the week, but eventually got tiring.

Next year we’ll not be right in the middle of the action.

Timing

The format of the meeting was:

• Arrive Monday – team dinner that night
• Tuesday: half day tourist activities, rented an office at a coworking space in the afternoon.
• Wednesday: Rented an office at a coworking space in the morning, flexible work/fun time after that.

All meals were together, so we had a lot of time to talk shop, and just as importantly to just get to know each other on a deeper level.

This is maybe the most important part of the trip: getting to know the WHY behind how we all are. As there are stressful or uncertain times at work (which, c’mon, there always are) it gives you that context through which you can frame someone’s behavior.

So, the retreat was 2 full days, a good bit of fun, and 3 dinners together.

I feel like this is a bit short.

Next year we’ll redo the format to be 3 full days, and have a good half the day planned for things like our annual Hackathon (more on this below), but then flex time in the afternoon.

In this flex time people can continue working on their Hackathon projects, do actual day-to-day work, or talk strategically about what the next 6-12 months will look like for us.

Working Sessions

Our two working sessions had very defined agendas, and were meant to maximize that productive period of our trip.

The Tuesday session agenda was as follows:

A ‘State of the Union’ talk

Here I highlighted our big wins from the last year, walked through our SaaS Metrics in the last 12 months, shared the financial investment of the retreat, and we had 2 working sections:

Playbooks

One thing we’re always trying to improve is our internal documentation. Playbooks are what we call them, and we spent time either listing out new Playbooks we want to create or updating existing ones. At the end, each team shared what they did.

OKRs

OKRs are a huge part of how each team’s weekly meeting goes, and as our meeting was early/mid June it was perfect timing to set our Q3 OKRs.

The Wednesday session was a bit different. Here we did:

Hackathon:

Each year we divide up into teams of 2-3 and work on creating something. This was anything from an MVP of a customer-facing tool, to internal processes, to a tool we use within the company.

Similar to the Playbooks, at the end everyone presented and a winner was chosen. Always has to be a winner!

Pictures!

We took team pictures this year with a professional photographer. Not bad, huh?

As you can see, we also got some pretty awesome swag for this year. Nice to show off Castos Originals a bit!

Attending WordCamp Europe

We have done team retreats that are associated with a conference and as standalone events.

Can’t say categorically that one is “better” than the other. They’re just different.

The plus side of doing the retreat right before a conference (I’d never do it after!) is that you pay for flights just once, and get to do 2 meetings.

The downside is it’s just a long time, and I probably wasn’t at full energy for the conference. I will be gone 8 days this week, and that’s just a long time away from my family.

In addition to WordCamp Europe, this year, we made the decision to attend the WordCamp Europe Contributor Day. As a company that participates directly in the WordPress space, I feel like it’s our obligation to give back to the WordPress community, and it was a great day.

Looking Ahead

I can’t help but start to plan the 2024 retreat in my mind. This week was honestly one of the most fulfilling 7 days I’ve had in a very long time.

There’s no doubt that everyone we have on our team is 100% the right person for their role. And the roles that we have 100% have the right people in them.

This kind of alignment is very rare in any company, and that’s where the Proud and Scared emotions come in.

I’m super proud of the company and team I’ve built, but at the same time very scared of messing it up. Particularly on the people side.

We’ve done a good job of hiring overall through the last 5 years of Castos, and it’s more important than ever to keep the caliber of team members extremely high.

Things We’ll Do Different

Not because they’re wrong, but because I want to have a bit of variety, next year a few things will change.

Format: next year we’ll do 3 total working days, with a half day structured session, and then flex work/fun in the afternoon. At most, we’ll have one structured non-work activity. Rest of the time I want people to be free to explore the area and their time with other team members. One thing we did last year in Chicago that I really like was an “Exchange” session where members of different groups would get together and work on a project. So a developer working with a marketer, etc. Cats and Dogs, I know!

Location: all 3 of our team retreats have been in large cities. Next year we’ll go to the countryside. Thinking about either Ireland or Tuscany. We’ll probably stay with the hotel model cause I think people like their space.

Onward

Overall, I’m just so happy. We leave the 2023 retreat as a tremendously unified team. Both in terms of what our company goals are, but personally connected and aligned.

This kind of ‘global’ alignment surely will mean some amazing things that we accomplish together in the next 12 months….until our next retreat!