A Western approach to choosing your next offsite location
Find an adventure that every one of your teammates will love
I’ve been called a cowboy, which is valid considering I’m from the West and spent much of my childhood on my grandmother’s horse ranch in Oregon. As I’ve grown, I’ve learned it’s best not to fight against my identity as a free agent embracing chaos on the open range of life. I’ve also learned the importance of a good fence.
As an adult, I’ve found my inclination toward adventure has afforded me skills in discovering unique locations and designing adventures for others. When company offsites really began taking off as Covid restrictions loosened in 2021, I was a busy freelancer, responsible for helping organize four of them each season. Now, as the Events and Employee Experience Partner at Medium, I’m planning twice-yearly offsites for a team of around 80, and I’ve found my appreciation for perimeters and parameters has helped me make sure every team member has a great time while in attendance. Here are a few things I keep top of mind when choosing a location for our team.
Know your team
Let’s start with the most important component of the offsite equation that will deeply inform the location you choose. Your team is the reason you’re even having an offsite, so before I even begin ideating, I like to do a little internal research and take some emotional inventory. First of all, what is the CEO feeling lately? Do a vibe check and let your exec team be your north star. Are there major accomplishments they’d like everyone to be celebrating? Is it crunch time and they feel it would be best to focus on work sessions? Keeping this research anecdotal is helpful. Meet in 1:1s, add a quick Q&A at the end of a staff meeting, check out the comments section in any of the culture surveys you may have done in the past. It’s in researching, discussing, and mentally logging those interactions with employees where you will find the color to paint your offsite canvas with.
Be strategic with timing
Offsite properties are almost always resorts and hotels that are open to tourists. There are high seasons where you might not be able to book even one person, let alone a corporate team. There is “shoulder season” when availability is more likely, like November in Cape Cod, and “off season” when you get the best rates, like April in Denver, and there is almost always availability. Seasons are different for every area of the world so take that into consideration.
One thing is universal: The hospitality industry is truly dynamic and has countless variables that shift and change daily, sometimes hourly. The best thing you can do to make finding a good offsite property easier for yourself is to start as early as possible. Plan a year in advance. I’m not kidding. I’ve found an absolutely perfect location before whose closest availability for a full buyout was 13 months away.
In addition to thinking about a location’s availability, you also have to consider the schedules and needs of your team. If you have parents of school-age kids, when is spring break? Are there dates that have a lot of conflicts, like early June (graduation season!)? If you’re an international team, what holidays or breaks do you need to consider? Send out a Google survey asking for everyone’s availability, differentiating between “works great!” weeks, “not ideal, but I could make it” weeks, and “definitely not” weeks. Once you see the clear front runner dates, let your whole team know which you’ve chosen to pursue. Then start asking for availability from properties. This transparency will save you time in the future and keep your team feeling listened to.
Be thoughtful when choosing flights
A large portion of your budget will go to flights.The parameters set by this aspect can be frustrating, and dedicating so much of your budget to something no one will necessarily enjoy isn’t fun. But there are ways to mitigate. Just like the hospitality industry, the airline industry has dynamic pricing, so the season you are headed to your locale will inform pricing here too. Also, depending on the days of the week you’ve chosen for your offsite, you can encourage your team members to travel on a weekday to save. But the number one best way to save on flight costs is choosing a destination near a major international airport.
Match the vibe
Taking into account that team research and inventory you did, what type of locale would work best for your team this time? Are you planning on focused, heads-down work time? If so, maybe a more remote spot with strong wifi and quiet nights are best. Are you wanting work sessions during the day and fun dinners at night? An urban setting with lots of options would probably be best. Locale selection can also be a great way to save on budget. A four-star property in NYC can be four times the price of a four-star property in Portland, OR. This goes for dining as well. I think of the team where the head of people and CEO wanted to throw a gigantic Halloween party for their staff of 200 to celebrate a recent milestone. I had to transform an entire ballroom from a space designed for a keynote speech into a spooky rave in an hour while everyone was at dinner. Luckily we chose a Sleepy Hollow-esque location that lent itself to the halloween aesthetic, while also providing the logistics of making it a possibility.
There is something I have to take a moment to address: tropical locations. Please consider your team members and their comfort level with wearing bathing suits around their coworkers. “If you don’t want to swim, you don’t have to!” you might say. Sure, but to me it’s a bit unfair to put all that in front of someone who may be apprehensive about being in swimwear with colleagues. I remember one team went to a resort with a lazy river. It was a huge selling point for the Head of People I was working with. He loved the idea of everyone swimming and laying by the pool. I think I only saw one person use the pool, once, that week. And it was during a work session they were skipping out on, no less.
How big will this place be?
I’m a firm believer in full buyouts. I think it was put best in Cris Beasley’s Medium article about offsites that our CEO Tony Stubblebine put me on to:
“Whether you have a group of 3, 30 or 300, your group should occupy the entire space. Size your venue so that you can rent the whole thing. A three-person team takes a regular house. A thirty-person team occupies a retreat. A 300-person team buys out an entire hotel or co-working space. What’s key is that anyone can walk up to anyone else at that venue and strike up a conversation, knowing they’re part of the same group. I cannot over stress the importance of this point. It changes the dynamic entirely to have strangers in the group. Everyone at the space must be a part of the event.”
Avoid forcing your team to have those awkward interactions with non-coworkers who happen to be at the same hotel. I remember one time at an offsite, someone just wandered into a happy hour, completely crashing the party. This person was staying at the hotel, so they thought it was just a happy hour for everyone (I can’t blame them). By the time they were discovered, they had already eaten some passed bites and mingled with a few folks. Spare yourself distracting interruptions like this by going with a full buyout. Trust me.
What is the design/layout like?
Consider your team. Would they like sleek, modern luxury? Are they more literary and would appreciate lush interiors with plenty of spots to curl up with a good book during down time? For me, it helps to envision individual team members interacting with the space. Think of a few of your colleagues who may be more introverted. Would they enjoy spending alone time there? For some folks, being away from home and their families is already intimidating enough. Hold space for the idea that the design of a location can help ease some of that stress. Is there a spot for folks to gather and play an impromptu game of Uno? Are there more secluded seating areas where meaningful heart-to-hearts can be had?
Consider your meeting space
Hotel basement meeting spaces with tiny little windows or (god forbid) no windows at all are my worst nightmare. They’re often drab and beige, a blank canvas for you to spend even more money on florals or tablescapes to avoid working in what would look like a prison cell without them. If your team is large (150+), you might have more limited options for venues, and there may be no way to avoid the bare-walled conference room. You’ll just have to get creative with decor and lighting. But if your team is ~60, you can really go wild. Consider taking over the hotel’s restaurant for the week, or maybe take a look at a nearby event space or another restaurant with some character that would be reasonable to buy out. I know it’s tempting to opt for the easy meeting space, but you’ve flown all that way to be together and you must make sure the precious time you do have is spent in an environment worthy of your team.
We booked our Medium spring ’24 offsite in Portland, Oregon. There were many factors that checked our boxes, but my favorite was that The Hoxton Hotel we are buying out is converting their restaurant into our workspace for the week. Huge windows with natural light, giant potted plants, and plush seating will be a feature our team members will get to enjoy all week instead of sitting in a hard chair at a banquet table in a basement.
Do a site visit
Lastly, visit the place! I’ve seen disasters happen. Teams do their best to vet a location via the internet, reading reviews, looking at photos of the space online, but when they arrive, it’s vastly different than they imagined, throwing the whole week off and ending in meetings with the hotel staff having to make concessions for how poorly things went. When you do take the time to do a site visit at an offsite property, ideas come to life. The room with the dark wood paneled walls? Perfect for a murder mystery night. The hidden basement bar? Perfect for a surprise late night karaoke party. Integrating your team’s wants and needs to the space will best be done by being in the space first. There is absolutely no way for you to confirm the space is right for your team unless you or a colleague has been there yourself. Considering how much time and money is going into your offsite, it really is worth it.
So much of choosing an offsite location has to do with attitude, intuition, and luck, but you can start by heading on out to the open range while keeping one eye on your fences.
