Recap and Lessons Learned From Sandhills Development Team Meetup 2017

Dinner time!

Last month the entire Sandhills Development team gathered together in Keystone, Colorado for our annual team meetup. This was not the first team meetup for the company but was different than anything in the past for a few reasons:

  1. The meetup was for five whole days.
  2. It was not tacked onto a conference.
  3. All employees were able to attend.
  4. The team is much larger than ever before.

Sandhills is a distributed team of currently thirteen employees from New Zealand, the United Kingdom, Canada and the United States. Every single day we collaborate and chat with each other in Slack but we definitely value the occasional opportunity to be together in-person.


Another aspect of the gathering which was different than in the past was that this was planned with minimal involvement from our founder Pippin Williamson. When I joined the company full time back in April, Pippin and I discussed the early plans for another meetup and I offered to help. He accepted my assistance and we then worked together over the next few months to explore options and figure out where and when to assemble everyone.

We bounced ideas off each other for a while and Pippin expressed the basic experience he was hoping for. I took that information and a few of my own ideas and began collecting a wealth of information to help us make a decision.


My first time in the Rockies

One of the first things I did when getting started was read carefully as many team meetup recap posts from other distributed companies as possible. I compiled a pretty good list and used it for inspiration throughout the process. Some of the better posts I found included:

These recap posts were pretty helpful for getting ideas on setting budgets, cool destinations, successful activities, whether to include family and other such decisions we were faced with.

Time and location were the biggest decisions to make and they took a while. In fact we even built a pretty detailed plan during mid-summer which we decided to scrap entirely and start over. This set us back a little but was for the best in the end. It definitely made me appreciate the fact that we had started the process early as it did allow us to make such a radical change without inconveniencing anyone but ourselves or costing us any money.


One of my goals during this process was to make the plan simple and avoid bothering the team with boring details unnecessarily. I’ve had too many experiences with committees and groups producing next to nothing over long periods of time and also have tremendous respect for the important work everyone else is doing at Sandhills so interrupting that was highly undesirable.

This attitude put the burden of most decisions on me, with input from Pippin. Even so, we did want to make sure everyone’s needs were met and those who had opinions got an opportunity to share them. There were three or four times this year that I pinged every team member individually with a question and curated their responses for consideration.

In the future, I’ll likely continue with a similar approach. This time around I did end up pinging everyone at least twice with questions which ultimately were inconsequential, though I could not have known that at the time. I’m committed to only disrupting everyone’s work day when I truly need input.

Feedback was certainly helpful though, albeit not particularly surprising. A warmer destination was often requested and most everyone hoped for someplace new and exciting.


After many iterations and many spreadsheets of choices with costs, travel times, team input and even average local temperatures, we eventually settled on renting a house in Keystone, Colorado. We liked the fact that the house offered plenty of comfortable looking rooms and had some decent hiking trails right behind it. Many on the team enjoy nothing more than hiking in the great outdoors and this location looked ideal for such activities. Additionally, given that this was a first time meetup for one third of the team and it had been a while for the rest of us, we intentionally wanted to plan for spending most of the time together as a group. Because of this we intentionally scheduled only a few activities and kept our agenda light.

The Result

By all accounts, the meetup was a success. Against the odds, we were able to bring everyone in, even brand new employees and some spouses. Attendees consisted of thirteen employees and five spouses. Everyone arrived and eventually departed without any serious mishaps.

During the week, we spent the vast majority of our time at the house. We enjoyed great food, productive discussions, beyond-expectations hiking and generally enjoying one another’s company. We ventured out into the surrounding towns a few times for dinners, a brewery tour and an escape room (which was a blast).

Lessons and Reflections

This project was definitely a learning process and I’m more than a little excited about starting the planning for our 2018 gathering. Here are a few takeaways from this year:

  • I worked pretty hard on providing the team with detailed instructions and helpful information. I kind of thought while doing it that I was doing a little more than necessary. I now believe that what I did was actually only barely enough and any less may have proved detrimental. In the future I’ll be sure to at least maintain but preferably increase the amount of information I share with the team and level of detail I go into on our trip itinerary.
  • We considered scheduling numerous group activities during the trip but in the end limited to only a couple dinners and the escape room. I believe this worked really well for us as most of us wanted nothing more than to just catch up and chat informally. More activities may have been fun but weren’t what we needed or wanted. This time at least.
  • Soliciting help with some aspects of the trip is not a bad idea. I got a lot of help from Tyler with our meal planning and he absolutely hit a home run. In the future, I may consider being more open to help in general. Being so immersed in the planning process and taking responsibility for all the details for so long did result in feeling something that wasn’t quite, but did somewhat resemble, burnout when we were actually there together. I may be able to engage better and personally enjoy the meetup more myself if I focus on the big picture and avoid getting consumed by technicalities and logistics. We’ll see.
  • There is no denying that starting early helps a lot. We were able to keep almost anything on the table and even start over from scratch after a few months of planning all because we hadn’t procrastinated. The main danger of planning too far ahead for us is not knowing how many new people we’ll be including by the time the meetup takes place. This year we hired three new people and parted ways with one between the time we started planning and when the retreat took place.
  • Keystone was super cool, there’s no doubt about it. But it wasn’t a sandy beach or tropical paradise. Many of the retreat recap posts I read about featured poolside discussions, surfing lessons, ziplining, historic tours, scuba diving and other such exotic pursuits. For some reason though, none of us minded the fact that our flip flops and sunscreen were left at home. Spending quality time together is paramount. It isn’t a honeymoon, it’s a work trip and picking a location where the focus could be on growing closer and collaborating more with minimal distractions turned out just fine.

That’s all! 2017’s retreat was dope and it’s only going to get better next year.

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