Retreat Planning for a Remote Company
The why…
Running a remote company doesn’t mean you have to compromise on personal relationships. This is a core value at Knack, and we’ve crafted our culture to foster interpersonal interactions with things like our Knacktail hours (virtual happy hours), book club meetings, and “better know a Knackster” sessions. These can all help build a tight-knit team, but they can’t compare to the organic rapport building that happens when you meet in person and spend time together to work, play, and bond as a team.
This is why we consider our bi-annual retreats to be one of our best and most important investments. In addition to reminding us that our co-workers are actual humans and not Slack bots, retreats reinforce what we’re doing, why we’re doing it, who we’re doing it for (❤️customers) — while strengthening our team bonds and reminding us of what it means to be true fuchsia Knackleheads.
The how…
Knack started doing retreats when there were just nine of us, so planning was pretty straightforward. It was easy to quickly snag some flights and an Airbnb last minute for a small team retreat. However, as our team continues to grow the logistics have become more and more difficult to navigate. Eight retreats and plenty of mistakes later, here are some of the hard-won lessons that we’ve learned along the way:
Have the retreats during the same time every year: We always have our winter retreat during the last week of January and our summer retreat the last week of July. Having those time slots set in stone allows team members to more readily plan their lives around those dates indefinitely.
Run the retreat during a work week: We’ve found that having folks fly into a single location from all over the globe often means that we lose two whole days to travel — the day of arrivals and the day of departures. We’ve also learned that committing three entire days to retreating is the perfect amount of time to get good work done, but also to get in some quality bonding. That five day setup fits neatly into a standard work week and negates the need for team members to tap into personal weekend time to attend.
Pick a setting that will meet your needs: Setting is everything! Here at Knack, we like to keep it fresh by visiting a new location each retreat. We also try to make location selections with weather in mind. This mitigates travel risks and allows some of our teammates to escape the extreme weather conditions of their hometowns.
Perhaps even more important than the location is lodging. The accommodations you choose set the tone for the entire retreat. If the building is too cramped, the rooms unclean, the beds too small, or the noise pollution too loud, it’ll make the entire week way more difficult to navigate. Here are some key factors that we consider when evaluating potential accommodations:
- No bunk beds or futons
- No more than three people to a bathroom
- Ideally no more than one person to a bedroom (but definitely no more than two)
- All beds must be queen size or larger
- There must be at least one communal space large enough for all hands meetings
- There must be at least one communal space large enough for all team dinners
- There must be at least at least one indoor and one outdoor breakout space for smaller meetings (or, alternatively, two indoor spaces)
- The main property must have strong enough wifi to support 20+ connections (we often bring our own Google WiFis just in case)
As we’ve grown, it’s become nearly impossible to find a single rental home that is able to meet all of the above criteria. As such, we investigate the following types of accommodation setups:
- Ranches
- Small hotels
- Multiple co-located homes
- Large Airbnbs with nearby hotels
Don’t rush food planning: Catering to the dietary needs and timezones of 20+ adults can be incredibly difficult, but very rewarding. While some companies opt to provide each attendee with a per diem or reimbursements for food expenses, we’ve found that eating together at the venue makes it easier to flow between sessions and facilitates spontaneous interactions. To make group meals go off without a hitch, you must dedicate a large portion of your planning efforts to this facet of retreat planning.
We’ve learned that trying to plan three meals a day for people from varying time zones is impractical and quite costly. Instead we plan two meals a day: brunch and dinner. We make sure that the brunch menu is full of hearty options to keep folks full until dinner. Additionally we make sure it is laid out for at least two hours so folks can eat at their discretion. Dinner times may vary retreat to retreat, but we always try to ensure that there is no more than a six hour gap between the end of brunch and the beginning of dinner.
We’ve also found that gathering information about each individual’s dietary needs well in advance can go a long way in mitigation and planning. It informs our hunt for caterers, and allows us to include these details in RFPs so the caterer is aware of the team’s specific needs right from the get go. We also keep several snack and alternative food items on site at all times so folks can graze throughout the day and so we have some alternative meal options in case we overlooked a dietary restriction when meal planning. (This will inevitably happen at some point, but having other food items on site goes a long way in mitigating that risk.)
If you’re anything like us, you’re going to end up with a ton of leftover snacks and food at the end of the retreat. Instead of throwing it out, we’d recommend investigating donation options with local charities and shelters. Many of these organizations will be incredibly grateful you thought of them and it feels a lot better dropping your extra food off at a charity instead of tossing it in the trash.
Don’t overbook the schedule: Although working sessions can be highly valuable, at the end of the day the main goal of retreats is to build stronger relationships across the team. As such, it is vital not only to include “fun time” slots, but also “open time” windows in the retreat agenda. These windows allow for organic interactions that might lead to a mini-adventure into the nearby town, an impromptu game of Pictionary, or even just a chill conversation on the patio. Additionally, these windows give more introverted team members the opportunity to step away and recharge.
Leverage your team: Even if you’re a solo planner, it doesn’t mean you have to go it alone. Leverage your team, when possible, to take some of the logistical burden off of your shoulders. See what kinds of sessions and activities the team is interested in. Ask for volunteers to assist with on-site logistics such as grocery store runs or game setup. This not only aligns the retreat with team interest, but also helps expand the bandwidth of the planner.
Also be sure to leverage team feedback before AND after retreats. Once a retreat ends be sure to gather immediate feedback so you can improve the planning and execution of the next retreat.
Plan ahead: Once you have a few retreats under your belt you’ll be able to plan more quickly, but we’d still recommend starting the process well in advance. The earlier you plan, the better your flight, lodging, catering, and rental van options will be. Although we’ve been guilty of finalizing sessions and activities at the last minute, we always start our location and lodging search at least five months in advance.
Advocate for personal wellness and boundaries: Although retreats can be a blast they also have the potential to be pretty taxing for some members of the team. Let’s face it, folks that work for a remote company often don’t spend a lot of time outside of their homes interacting with large groups of humans. When you take those same individuals and put them in close quarters with 20+ other people for a week, it can be pretty overwhelming. To alleviate this issue, be sure to set aside some free time where folks are able to step away to recharge, rest, and/or call home as needed.
Over communicate: In addition to advocating for wellness, communication can go a long way in making retreat experiences less overwhelming. Over communication can also mitigate food and travel issues, surface questions for the broad team, familiarize newbies with the retreat process, etc. One tool that we’ve implemented to this end is a retreat travel brochure. Before each retreat we distribute a brochure that consolidates all of the finer details of the upcoming retreat for easy reference. These brochures include details about:
- Ground transportation
- The local airport
- The catering menu
- The lodging address(es)
- Rooming assignments
- Recommended items to pack
- Contact information
- Expenses and reimbursements
- Getting the most out of the retreat (see below)
Trust your work: Once you’re at a retreat trust all of the front work that went into making it possible, kick back, and have fun with your team!
Getting the most out of retreats…
Once a retreat is rolling we like to remind our team to:
Build some strong relationships and have fun doing it! Retreats are great ways to get to know members of the team that we may not otherwise get to work with on a regular basis. Make an effort to reach out across teams whenever possible. Sit with someone different at each meal; go on a walk with someone from the dev team; bounce big ideas off of one another.
Make it sustainable. We all want to maximize retreat time, but folks shouldn’t feel the need to sacrifice on sleep, or like they can’t call home, or bow out of something for some re-charge time.
Be respectful. As remote workers we are all becoming increasingly desensitized to social norms. If you’re up late, respect that others are sleeping. If you’re loud, respect that you’re diverting attention from others. If you’re used to pantless video calls, wear pants.
Leverage the fact that we’re all together. We should bias towards brainstorming, consensus, group execution, and strategy over getting typical work done.
Don’t be afraid to let our customers know we’re on a retreat in order to create reasonable expectations for responses. They will appreciate the fact we take the time to do large-scale strategy sessions to make a better product for them.
Have fun, get to know each other, and make some memories! This is goal numero uno. The absolute best part of each retreat is cementing the bonds we create remotely.
