Jun 21 · 6 min read

During a vacation in 2018, my wife and I met a striking woman. It was Mothers Day and we sat next to her at a restaurant her son was working at. We shared part of our dessert with her and got to talking. She was older, maybe mid 70s, and was actively running an impressive farm and residence in rural Maui. She managed to do this all completely off the grid, completely on her own. Blown away by her daily regimen and the understated, humble way she spoke about it, I asked if she had any advice on how to run a farm or a family.

“Front-load” she said. “Do the work up front, and it will pay off double on the back.”

Nearly a year later, I find myself in a restaurant at San Francisco International, possibly the most relieved person to sit over a bowl of airport ramen. My team has just finished a week-long offsite and we hit our goal and I’m contented. Offsites can go any number of ways and returning home with the output we wanted not only helps justify future trips, it puts every one back on the plane with what pep is possibly left in a post-sprint step.

Offsites are attractive for the obvious reasons — minimal distractions, team bonding, change of scenery, visiting friends after work — but they can easily dissolve into a sitcom-worthy wayfinding expedition if you’re not careful. If you’re planning a team offsite, here’s several things we did the the three days leading up to the trip that helped us be productive without sacrificing fun.

Day 1: Context before Concourse

Before we set out, we spent the two and a half days leading up to our travel weekend preparing for the offsite. To my surprise, making the agenda was easier than I expected. Turns out, if you just answer the questions most people have when they’re asked to endure airport security for work and order them in a way that tells something of a narrative, going from general to the granular, there’s a clear gravity that pulls together the focus of the trip:

  • What do we want to get out of the trip?
  • Why is this valuable?
  • How are we going to do it?
  • How do we know we’re on track?
  • Where do I come in?
  • When should I arrive and what does the day look like?

By clearly answering what we wanted to leave the trip having completed, it helped orient all the other questions. We were there to build 12 new web applications students would build off from as part of their weekly homework. We were also there to have some fun. While the latter reason was hopefully assumed, I think it’s always nice to confirm that we could do all we set out to accomplish and also take hour-long lunch breaks during the day.

While having a clear goal is important, perhaps the more important question to answer is why this output is valuable. Most people want more purpose out of a trip than to visit another co-working space. They want to know why it justifies the team’s single focus. We answered this question by answering it from different perspectives:

  • Why is this output valuable to the student?
  • Why is this output valuable to our team?
  • Why is this output valuable to the future of our product?
  • Why is this output valuable to you as a person?

I am fortunate enough to attract talented people who genuinely care about creating the best student experience. By explaining how the goal of the offsite impacts students, getting buy-in from your team is easier.

  • Why is this output valuable to our team?

While team-bonding is a given, it’s worth mentioning so that the team knows that the focus isn’t entirely about cranking out work, and that fun is a priority too. Ahead of of the trip, a teammate local to San Francisco got reservations at a brewery near our co-working space for one night and dinner reservations at a spot near their home the night after. Not only was this essential for the San Francisco food scene, it also showed that these experiences were valued as highly as the work we would be producing.

  • Why is this output valuable to the future of our product?

Sometimes answering the first two questions is enough. However, I’m again fortunate to have a really smart and motivated team of developers that needs more. Demonstrating how the output of the offsite contributes to an upcoming roadmap and a larger strategic vision beyond helped us create material that played nicely with upcoming projects outside our team, and moved our curriculum toward a future we are proud of.

  • Why is this output valuable to you as a person — personally and professionally?

People look for different things when they travel. It only makes sense then to share why you chose the location in the first place in order to show how their individual desires were considered. For us, San Francisco hit a number of boxes that appealed to our team:

  • Craft beer scene
  • Museums and history
  • Family-oriented
  • Nature
  • Tech
  • Likelihood of seeing friends outside of work
  • Unquantifiable cultural appeal

Aside from the physical location, offsites can be doubly impactful if the work being done is not only important to the team, but also enjoyable. Like I said, I’m super fortunate to have a team of ten engineers who are not only talented full stack web developers, but incredible curriculum writers who create industry-relevant online and classroom learning experiences. Although I lean much heavier on the learning and curriculum side, I know that my team sees themselves as engineers first, and that’s part of what makes them so good. I knew that our team wanted a break from writing lesson plans and modules and that technical work it takes to create the mock applications students would experience was the type of work that would be most satisfying to them.

Day 2: Rehearse over Recourse

On day two of prep, we went over what a day would loosely look like in San Francisco. We went over what role everyone played and what was to be accomplished at check-ins. Then, we did a dry run, following the same schedule to reach, just barely, a deliverable we new we needed to hit each day in order to achieve our end goal. Having cut it down to the wire, we knew there was a few things we needed to tweak before the following Monday.

For me, this was particularly helpful as it validated our initial thoughts on how our engineers would work together and whether our approach to feedback was good at nudging teams towards quality and timely work. For our team, I think it gave them some relief that what a daily goal was would be feasible when they got to it and had more repetition as the week progressed.

Day 3: Siesta before the Fiesta

On the third day of prep, the Friday before heading out, our team ideated what homeworks they could build in San Francisco. Using a rubric we developed to evaluate the learning design of our homework, we tapered the list of ideas down to a manageable list we were all excited about. Halfway through the day, we stopped work at noon so people could be with their friends and family before committing their Sunday afternoons to travel. While our team had the option to bring their partners and family along on the trip, it’s not always easy to make that happen. A team siesta, with plenty of notice before hand, hopefully let everyone get that time back with the people they love.

Let it Happen

Aside from one teammate getting sick, things went smoothly in SF. We followed our loose daily agenda, of kick-off, check-in, lunch, and scrum. We we’re constantly on but the pace was appropriately, even delightfully, Californian. With a lot of the work front-loaded, we were able to hold more substantiative 1:1s, do proactive planning, and even get some time to be makers again. A daily standup at the end of each day made sure the authors of each application considered vital questions addressing the student experience (how does it align with learning objectives? How does it support transfer? Is this feasible with their abilities? how is it appropriately scaffolded? Is there an advanced route for stronger students?)

Looking back on the trip, I’m amazed how well it went. As a remote team in a rapidly growing company, ambiguity and change is constant. Being able to focus on craft in the same space as your teammates and see San Francisco while doing it was just the work trip we needed. I’ll have to visit again to see the bridge.

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EdTech Product Design & Management

The Startup

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