Insights from Our Simplecast Offsite

(Or, Why Our Entire Team Spent A Week in Troy, NY)

At Simplecast, we love being a distributed team. The depth and breadth of diverse talent we’re able to bring on board because we’re all remote has helped build a company and a culture with incredibly smart employees from a wide variety of backgrounds. We’ve worked hard and are proud to have a team that is diverse in every sense of the word–skills, education, ethnicity, religion, age, region, politics, socioeconomic status, LGBTQ, veteran status, upbringing, “bubble”, personality type (as we learned this last week!), and in so many other ways.

But that’s not to say having a distributed team is without its challenges, that we don’t have to work incredibly hard at proactive communication and collaboration, or that we don’t need some face time every once and a while! That’s why we took planes, trains, and automobiles from New York, California, Texas, Maine, Michigan, Kentucky, Utah, Florida, Arizona, and Pennsylvania to meet up at the Troy Innovation Garage in upstate New York for a full Simplecast team retreat. Here’s some of our advice for how to have a super productive and successful offsite!

Get the Timing Right

There’s no “right” amount of time for an offsite. How long you should plan to spend together depends heavily on how often you get together, how big your team is, and what you want to accomplish with the time. We found that you do need to spend enough time together to get things done and have fun. But bear in mind you don’t want to spend so much time at an offsite that it hurts your business, people stop focusing, or the amount of time away from home is a burden on the team and their families. We spent Monday through Thursday together, and that felt just about right.

Let Yourself Focus on the Retreat

Our customer team normally does two webinars a week–they’re super important to us because they help us educate our customers, while also getting a window into their concerns. During the retreat, we did none. Did it feel a little weird? Sure. Were we able to focus more fully and be more present? Definitely. Consider shuffling around your team’s responsibilities for the week, setting a coverage schedule, or implementing a “sorry for the delay!” email auto-responder.

Make Big Decisions

Don’t just ask the big questions or have big brainstorming sessions–use having everyone in a room together to firmly nail down plans, next steps, and timelines. What does our product roadmap look like? Where do we fit in the ever-changing podcast ecosystem? How do we best work with our partners at Apple, Google, Spotify, Luminary & Pandora? What are the most important things we’re working on and how do we keep the main things the main things? What are our values as a company?

We needed to completely reset our focus from our recent launch of the all-new Simplecast our new big initiatives. So we wrote our mission, vision, and values (keep an eye out for those soon), prioritized the next things on our product roadmap, and outlined what we believe are the big needs for podcast creators now and in the future. Having everyone in a room together means truly getting into alignment and letting everyone have buy-in.

Mingle!

Incidental interactions–those tiny moments in an office where you hear some nugget of information another team is working on–are super important, and something we can miss out on because our team isn’t always in the same room. It was important for us to break down the silos that might be happening like between marketing and engineering teams, or our customer support team and our front-end team. Because of this, we made sure we had some unstructured hang-time–things like nature walks, game nights, chili cook-offs, and team dinners built into the schedule. Depending on how large your team is, you might want to formalize this by doing a company mixer, or group activities where you pair up employees that don’t normally interact with each other.

Have Tough Discussions

Let’s be candid: sometimes communication across a distributed team is hard. No matter how many emojis you include in that email, how many GIFs are in your Slack message, or how many times you encourage people to use video during your all-hands, some level of tone and intent is always going to get lost if you’re not face-to-face. It’s also just really difficult to build trust amongst distributed teams when people don’t have the same opportunities to get to know each other that often come through casual in office interactions and after work time together that happen when everyone works in the same office. That’s why a retreat is a perfect time to have tough discussions.

So, we talked it out. We talked about communication and what was working and what wasn’t. We talked about each other’s personality types, at work and outside of work. We talked about our values and who we want to be as a company and as people. We made community agreements about how we would show up for each other and how we can work together most effectively. We talked a lot about diversity at our retreat–what that means to us as a company, and how we will always be striving to do better and better. Part of the reason that these conversations were able to be so honest and generous was because we were all in the same room and because we had spent a good amount of time before these conversations becoming friends, not just co-workers.

Do Good With Your Local Community

You’ve got your whole team in one place–what better way to use your combined powers than for good? We joined up with Mission Accomplished, a local non-profit created to help teens transition into college. We put together “welcome home” boxes for returning students, including some of our favorite books! Sure, it’s important to do good for Simplecast at a company retreat, but it’s also important that we do good for the community that was hosting us!

The aim of our retreat was to energize, motivate, and inspire our team–and I’m happy to say we did just that. Did it take a lot of planning? Yup. Will we be doing it again? Absolutely! Thinking of bringing together your own distributed team? Drop us a line, or invite us on your podcast–we’re excited to help!

Many thanks to Josh Pigford, Founder and CEO at Baremetrics (and long-time Simplecast customer with his podcast Founder Chats) for his invaluable advice on how to have a successful offsite with a distributed team, Paul Sieminski at Automattic (the makers of Wordpress and one of the largest and most admirable distributed workforces) for always having helpful tips on how to build and foster cohesive distributed teams, and Hudson Valley Startup Fund for their hospitality and belief in us from the very beginning.