For Offsites, No Plan is a Good Plan

Sandy Kwon
September 27, 2022

At Sym, we meet every 6 months for a week-long offsite as a company. We held our third offsite this past month in Belmont, MA, a few miles outside of Boston. We rented a large house and adopted an unorthodox approach to planning - by not creating an agenda. Fortunately, this isn’t a blog intended to mitigate any public relations nightmares. If you’re wondering what happens when you sequester a close-knit, highly motivated, and self-directing team with unlimited unstructured time, keep on reading!

Our Offsite Culture

We’re a bit unconventional in our decision to operate 5-day offsites. This is both a long time away from home and a lot of face time with your colleagues, but we’re fortunate to have a team that really likes each other and excitedly opts into it each time. We’ve found that 4 nights and 5 days works for us. This allots substantial time for organic bonding and free flowing brainstorming without the pressure of an overloaded schedule crammed into 2 or 3 days.

So with that said, here’s a non-exhaustive summary of how we spent our time…


We’ve historically incorporated a pre-planned strategy session or hackathon for each offsite, but this time we let the team decide if and when we’d have such an event. I’ll let our teammate Leslie share the impetus and outcomes for our “not-a-hackathon”.

“We knew that we wanted to dedicate some time to tackling the big, theoretical, brainstorm-heavy problems that are difficult to do asynchronously over Zoom. These sorts of collaborative brainstorms are difficult to do remotely because of all of the overhead that comes with video calls (it’s hard to hear people if multiple people overlap, it’s hard to think quickly because you have to wait for your turn, you lose focus because you’re staring at a computer screen).  

One of the cool things about the discussion was that we actively decided to not think about the constraints and boundaries of the current system. Instead we started from “what do we ideally want” or “what could the system look like” and worked backwards from there.

When you start a conversation by saying “ok, let’s not think about what we can or cannot do right now,” it gives you a safe headspace to throw out crazy ideas that seem impossible. And (as we experienced) you’ll find that when you dig into those crazy ideas, often you can identify baby steps that can take you towards a concrete solution.

One of the things that we wanted to solve was how to combine our Custom Strategy Framework and our AWS Lambda Strategy. These two strategies have really similar end-goals: to be able to integrate Sym with a system that isn’t natively integrated.

I personally loved that because we were in a shared space, we could move around and take breaks naturally, and the discussion felt organic, rather than a forced meeting with an expected outcome. We started the session in the living room by mapping out customer examples (who needs a whiteboard when you’ve got a massive 80 inch TV); and as we started to get restless, we started to move around to grab snacks and take a quick break. The big brain moments actually ended up happening around the kitchen island while nursing fresh cups of coffee! This honestly felt like the epitome of the start-up experience.

We came up with some really slick ideas that are definitely future-looking, but what’s awesome is that some of the things that we previously thought were impossible now seem achievable and we identified several things that can be done in the immediate future to get us towards that vision. Eliminating the pressure of a structured hackathon and the freedom to have fluid and boundless conversations created so much space for creative thinking and I can’t wait to see what we’ll come up with at future offsites.”


One exception to our unplanned offsite was that we knew there would be an in-person retro led by our two-for-one VP of Engineering and team coach, Nick. (Read more about his retro philosophy here). In his words, here is some context around our retro culture and a peek into how this offsite’s session went.

“One of our cultural touchstones at Sym is building an exceedingly safe work environment for our whole team. People are able to do their best work when they know it’s safe to say “I don’t know”, to ask for help when they get stuck, to try new things, and to make mistakes. One of the most important components of this focus on safety is retrospectives.

Every couple of weeks, we come together to openly and honestly discuss what’s going well and what we’re not so satisfied with as a team. We have an anonymous component to make sure there’s a safe way to share even the things that might feel a little scary to say out loud, but as our trust has grown, we’ve needed to rely on anonymity less and less to get those things into the conversation.

At our offsites, our retros are a little different. Instead of focusing on the last couple weeks, we’re focused on everything that’s happened since our last offsite. Instead of jumping straight into talking about good and bad, we start by building a shared timeline of the critical moments in that time period.  We inevitably spend some time along the way discussing those moments, but the best part of the timeline exercise is helping us all realize just how much we’ve accomplished over the last several months. It’s easy to lose that perspective in the day-to-day rhythm of a fast-moving company, so it’s really important for us to take a step back and give ourselves the credit we’re due.

We end our offsite retros by writing “kudos” for our teammates on post-its and sticking them on the wall. There’s always a bunch of post-its for individual things people have done, but there’s also things that land at a deeper, more human level, calling out an individual or group for who they are or how they’ve grown. We have big ambitions for Sym, and we’re convinced that building the kind of team that values each other as people, not just contributors to the business, is one of the keys to getting there.”

Customer Event

At every offsite, we dedicate one evening to spending time with our customers and partners. This gives us an opportunity to thank them, introduce them to the larger team, and connect with them on a more personal level. For this offsite, we were joined by our friends at HYPR, SaaSworks, some prospects that we’re excited to be working with, our blog contributor Brian Tarbox (check out his articles here!), and Don Luchini, a friend of the company and a Boston DevOpsDays organizer.

To prepare for our barbeque, Nick and Max planned the menu and prepped all of the food, while the rest of the team tidied up the house and set up our patio area with beverages and hors d’oeuvres. It was really touching to see how organically this teamwork happened, as not a single task was assigned to anyone. It also felt really special and personal to be able to prepare a homemade feast for our guests.

Our time was spent providing tours of our quirky house (did I mention it was previously owned by Mitt Romney?) nerding out about security, and my favorite part of the evening: the ritualistic bonfire.

Commence With the Burning of the Tech Debt!

At one point during the offsite, someone proposed the idea of burning Slack messages related to a project that we were excited to put behind us. There was zero intention of doing this in front of our guests but by this part of the evening, they had cemented their place as friends of Sym and we wanted to include them in this celebration.

It’s always rewarding to broadcast your wins with customers and prospects, who you’d hope would ingest these signals and get excited about what you’re building. And sure, signing contracts and exchanging products for services are the de facto indicators of support, but nothing tells you they’re bought-in like being able to transparently unveil your growing pains and have it met with unbridled encouragement and enthusiasm.

Bonding Without Even Trying

Neda treats planning like a sport and conscientiously thinks about every possible activity we can book to make the team happy. After having executed a couple of meticulously planned offsites, we realized that you could trap us together in a house and we’d still have a blast - which is exactly what we did. She invited everyone to creatively surprise the team with various (frugal) bonding activities and I was humbly reminded each night that it’s not what you’re doing, but who you’re doing things with.

On our first night, we played The Witch is Dead, moderated by our newly minted Tech Lead Ari. On another night, Nick and Max thoughtfully used their one-year anniversary gift stipends to treat us to a mezcal cocktail-mixing course (courtesy of Flix&Cheers… thanks Rebekah!). Adam also took us on a nature walk through the Middlesex Fells Reservation, where he reminded us that he was an all-star college athlete and really cool despite his nerdy penchant for bad dad jokes. Andrew, our resident gentle-person, introduced us to a couple of board games that brought out the aggressively goofy and competitive sides in each of us. We also finally gave Jon the karaoke night of his dreams and I’m pleased to announce that we are officially a karaoke company.

I’d need another 1,500 characters to cover the small, yet immeasurably meaningful moments from the week - like watching Tarek and Adam play ball in the front yard, or the lightning fast Product retro Max led where we realized we achieved all of our 2022 goals and then some.

It takes an incredible amount of trust, faith, and collaboration to pull off a week like this, and recounting our offsite reminds me why I’m so grateful and lucky to be able to call this my team. This also feels like an appropriate spot to insert a not-so-shameless plug, but we’re hiring. Karaoke skills are a huge plus.

And to wrap up this recap, here’s a photo of Max’s dog Pickles, who chaperoned us all week. We couldn’t have done it without her.

Recommended Posts