Last week, the Oso team went to Hemlock Neversink in the Catskills for our annual team offsite. We were excited to use the time for team bonding, reflecting on the year behind us, and strategic planning for the year ahead.
Why Offsites Matter
It’s easy to get caught up in emails, meetings, and deadlines in the daily grind, but there’s something special about a change of environment that helps foster deeper connections and break down silos. The casual atmosphere of a retreat allows us to be less guarded and express ideas freely when we are not confined by the formalities of the office.
Designing a Gathering
This was my first true offsite ever. Previously, I had participated in offsites within NYC, in an office space for a week with colleagues—quite literally an “onsite”. So I wasn’t sure what to expect. After all, who enjoys a corporate-mandated “fun” session with some lazy team-building games, right?
Last year, I read (and loved) The Art of Gathering by Priya Parker. The book emphasizes the importance of intentionality in bringing people together, advocating for meaningful, purpose-driven gatherings rather than simply gathering for the sake of it. Parker argues that how a work gathering is designed can profoundly influence its success—in other words, what you put in will determine what you get out. We agree.
Paloma, our EA, did a fantastic job designing our offsite. Whether it was team dinners, HIIT classes, candle-making workshops, hiking with goats, or a Tai Chi session, everything was thoroughly planned, well-thought-out, and fulfilling.
Montana and Ege dj’ed for the last day’s party, I tattooed at night, Ash had his first s’mores around a campfire, and we all got our birth charts read.
What Craps Can Teach Us About Access Control
One night, some teammates and I visited a casino about twenty minutes from the retreat, where I learned to play craps for the first time—and promptly lost more money than I’d like to admit. Shared wins build camaraderie, but shared losses? Even more.
Craps is all about managing risk, applying the right rules at the right time, and adapting to changing conditions—just like authorization. That’s the only reason I went, obviously: to become better at my job.
Team Building
Throughout the offsite, I found myself appreciating the diverse skills and perspectives everyone brings to the table while getting to know them on a personal level. Here’s a brief list of some things I learned about people I see every day:
- Even though Ash is from the UK, he’s never tried blood sausage.
- Montana’s laundry soap smells amazing.
- Greg is currently reading “How to Be Both.”
- Stephie cuts her kid’s hair herself.
- Carl’s mom is a ballet dancer.
- Fernanda likes bananas.
- The majority of our team enjoys deep tissue massages so intense they feel beaten down, crushed, or run over by a truck rather than the typical gentle Swedish massage.
A good team is built on trust, respect, and shared values, creating a sense of unity and purpose. If you don’t know each other well, you won’t know how to make each other feel appreciated, and cared for. When you understand teammates beyond just work—recognizing their motivations, and struggles—it fosters genuine trust. You’re more likely to assume good intent in conflicts and support each other during challenges. It’s easier to stay motivated when you feel like your teammates truly care.
Strategic Play
We also dedicated time to focused work. We had marketing, developer relations, sales, and engineering workshops where we brainstormed and solved complex challenges.
We also participated in a Crucial Conversations workshop, designed to help us navigate high-stakes discussions with confidence and empathy. The session focused on mastering dialogue in situations where opinions differ, emotions run high, and outcomes matter. We were encouraged to come prepared with real conversations we were struggling to start—whether with colleagues, managers, or even outside of work. Through guided exercises, role-playing, and group discussions, we learned how to recognize when a conversation was turning crucial, stay in control of our emotions, and create a safe space for open dialogue.
It was an eye-opening experience that equipped us with practical tools to approach difficult conversations with clarity, ensuring they lead to productive, rather than confrontational, outcomes.
The Offsite That Authorized Stronger Bonds
We reflected, recharged, engaged, and returned to work with a renewed sense of focus and motivation.
If you want to be in the next offsite, we are hiring. At Oso, our guidance has always been to "build authorization around the application, not the other way around." We apply the same approach to our team: building the team around the product, not the other way around. We are doing the hardest but also the best work of our lives, with the best team possible.