Lessons Learnt On Receiptful’s First Retreat

Receiptful was only a couple of months old when we met up for our first team retreat in March this year.

At the time, we were 5 team members (now 7) who had never met each other in person nor worked together in the same space. Having regular team retreats was something that we spoke about as early as my initial hiring interviews, as we acknowledged that (as a distributed team) we needed to invest in team-building (which is huge component of remote work in startups).


Retreats were something that I was quite familiar with having experienced a couple of them during my time with WooThemes. I can remember our first attempt at this getting covered by Mashable, but also how misguided some of our decisions were… As an example, we didn’t get much work done on that first WooTrip and dealing with customer support in a timely manner was a particular challenge.

(The most recent WooTrip has definitely upped the game in this regard though. Also considering that it now needed to cater for 50-odd individuals, instead of six of us on the first iteration.)

Through this experience though, I knew that it would be important to avoid the many potential pitfalls associated with hosting a successful retreat. In that sense, Baremetrics’ retrospective about their retreat helped me significantly in planning Receiptful’s first retreat.

With the growth in popularity of remote working and distribute startups, retreats as co-working and team-building exercises will just become more popular. With that in mind, I’d like to share a few of our takeaways with the hope that the next startup organising their first retreat can improve on our decisions and experiences. :)


1. Setting goals and deciding on a schedule

Our primary goal for the retreat was to get to know each other and building those relationships. It’s no real surprise that Buffer (probably the most well-known distributed startup) places such high value on this: better relationships makes for better collaboration.

Beyond that though, I also wanted us to get some actual work done. This was partly because it would help in the getting-to-know-each-other stakes, but also because we’re a very young, growing startup that couldn’t ignore our to do lists (which is always bursting at the seams).

In that sense we had a vague discussion before the retreat about what the 5 days we were spending together would look like. What happened in the end though was slightly different to this.

We ended up mostly working for the first two days and then spending the subsequent two days team-building. That meant working a bit in the morning and evening to handle urgent stuff only.

I think in that sense the end result was better than it would have been had be implemented the initial schedule we had in mind, because the schedule itself became a collective decision and collaborative effort. It was also very flexible in considering our moods, needs and aims on any particular day, which we could not have done by having a rigid schedule that was planned months before.

Key Takeaway: Be clear about your goals and flexible about your schedule.

2. Picking an inspirational destination

The decision of where we’d meet up was interesting to say the least.

I’m based in Cape Town and my team members across Europe. So it made sense to meet up somewhere in Europe. My initial idea was to meet up in London, as I had other business to take care of there, so that was the most efficient choice. It was also a big city with busy airports, which made travelling there significantly easier and cheaper.

The team though were trying to get away from the shitty winter weather they were experiencing, which meant London (in March) was not a great option. This meant migrating as far south as possible.

The ultimate decision was Sicily, Italy, where we rented this beautiful villa on Airbnb:

Not bad.

This was out in the countryside and was about a 45-minute from the airport and Catania city center. To be brutally honest, I did not realise this when we booked the villa and was ignorant about the fact that it would require us driving everywhere.

Luckily we had planned to rent a van for the duration of our trip, so that didn’t end up being a problem. In fact, the driving actually meant that we saw a much bigger part of Sicily than we would have had we been based in the city center (where everything would’ve been too convenient and comfortable).

It goes without saying that a shitty destination would’ve resulted in a shitty experience. The combination of having mostly good weather (much better than London would’ve been) and being made to explore a new destination, definitely infused our retreat with inspiration and positive energy.

Key Takeaway: Don’t go mainstream and let the team decide where they’d be most inspired.

3. Food unifies

Great plans being concocted

There’s very few ways to bond that are better than bonding whilst sharing good food and wine.

We were really fortunate in this sense that our Airbnb villa had a spacious kitchen with a big table that could accommodate the whole team at meal time. It however doubled as our workspace during the trip too and we subsequently spent a lot of time in the kitchen cooking together, working together and eating together. This sparked so many great conversations (about work and other stuff) which created a solid foundation for the rest of the retreat. (This was also augmented since we had a native Italian on the team who showed that he is equally adept at cooking Italian meals as he is with Javascript.)

Beyond our own kitchen though, we had similar awesome experiences when we were having meals on the road. Many a great idea was sparked as a result of enjoying equally great pizza. I remember a particular discussion over lunch in Syracuse, where we planned out the whole analytics section of Receiptful.

I also had a new experience on this trip which was different to any time that I got together with the WooThemes team in the past. Woo tended to have quite a boozy culture, which meant many late nights and a lot of beer. And along with my co-founders we were the leaders of that pack.

The worst side effect of this was always the odd hangover the morning after and generally this was just part of our DNA. It was also much less about actual alcohol and more about fun.

In contrast, we didn’t do a lot of drinking on the Receiptful retreat at all. This actually meant getting more sleep, earlier mornings and having deep, philosophical conversations (like the freedom to choose not to work and live on government grants). This wasn’t necessarily better than WooTrips, but it was different. I’m mostly glad having skipped any hangovers, but I also missed those crazy experiences that one remembers vividly years after they happened.

Key Takeaway: Sharing good food and wine is the catalyst to great conversations.

4. Create personal space

Since we were based out in the sticks, we were limited to doing everything together. If we were based in the city for example, I’m sure we would’ve individually snuck out to grab a coffee or Cannoli.

This meant that we were in each others’ space for most of the time during the five days we spent on retreat. Luckily there was no negative experience as a result of this.

I did however get the feeling though that were we to spend longer than five days together, it would’ve gotten quite tiring not having your own space and autonomy.

Key Takeaway: Make a plan to create personal time and space for team members.

5. Delegate to beat leadership fatigue

As founder I make a lot of decisions on a daily basis. This means that I sometimes seek the exact opposite: not making any decisions (especially as I’ve burnt out in the past).

To this extent, I tried to delegate as many of the decisions on the retreat itself to the team. Things like deciding what we’ll do for team-building, where we’ll go for day trips or where we’ll eat lunch / dinner were decisions that I didn’t make (on my own or at all).

This was refreshing as I could take a break from the normal decision-making mode. But it was also great seeing how the team made decisions as a collective and how individuals within the team would take the lead on those decisions.

Key Takeaway: Founders and / or managers don’t need to be the only leaders on the retreat or make all of the decisions.

6. Don’t try to quantify the experience

The natural thing after an investment such as going on a retreat is to try quantify the value one derived from it. This is especially true for startups where budgets and resources are normally constrained and thus need to be optimally invested.

Tallying the numbers after the retreat, I know that we spent almost $10 000 USD to bring the team together. There’s however no way for me to say that this investment has generated a ROI of x%.

What I do know though is that we’ve made great progress (as a company) since the retreat and that there’s definitely a sense of togetherness and shared purpose in our communication.

I’m also reminded on the effect that in-person meetups had for me during my time at WooThemes where I’d meet up with my co-founders and spend time together. Whilst our communication and combined decision-making wasn’t always perfect or easy, it felt much more natural after we’d spent time together.

That value is hard to even try quantify, but that should not detract from the fact that getting together and going on retreats offers significant value to startup teams.

This sometimes makes it hard to justify to stakeholders or investors, but that should not deter you from hosting your first retreat.

Key Takeaway: The benefit of a retreat is obvious, but don’t try to quantify it.