Why a location scouting trip is a must for a great remote team retreat

As a remote team, we’re very intentional about coming together once a year for a week of bonding, relaxation, and good plain fun. We find a lot of value in operating as a distributed team (hire talent from anywhere! set your own schedule! work-life integration!), but one of the biggest struggles is keeping everyone engaged with one another as people, beyond just as colleagues and coworkers. To that end, this annual in-person time goes a long way in setting the tone for team energy and collaboration throughout the rest of the year. For many, it will be the first time they meet the rest of the team outside of Slack and Zoom!

There’s a lot riding on this week. Planning a meaningful, memorable retreat is somewhat of an art–and we treat it as such. Last year, we wrote a recap of our 2018 retreat detailing much of our planning and thought process. This year, we’re taking you even further behind the scenes with a series of posts.

First up: why you should take a scouting trip to your intended retreat location. If your goal, like ours, is to host a smooth, fabulous retreat for your hardworking team, then trust us when we say a scouting trip is a need to have—not a nice to have—part of your planning process. Photos and reviews online are one thing, but there’s just no way to really understand what the layout, energy, and quality of a place is like without visiting it.

After evaluating maybe 35-40 properties (more on this in a separate post!), we narrowed in on the Dunskey Estate in Scotland.

Just me and the friendly neighborhood sheep out there!

Successful scouting trips require you to organize your thoughts in a few areas to make sure you get all the information you need. Without some pre-work, you can very easily just show up, look around, and say, “I dunno, looks nice, I think this will work?”

To keep myself on track, I spend some time before I go listing out any questions I can think of that relate to three overarching areas: travel, accommodations, and activities. While I’m on the trip, I jot down anything and everything that I experience in my notebook (yes, I’m old school like that–Moleskines are life), and then use those notes to present a recap to the rest of the team before we make a final decision on whether or not to commit to that particular location.

Travel

What’s it like to get there?

Our overall goal here was to evaluate not just the logistics of traveling to Dunskey, but also how that travel actually felt. Keeping the energy of your team members in mind at all times is a big part of designing a successful retreat. For travel, this means contextualizing the logistics within the emotional/physical experience of those logistics. You can have the world’s most glamorous accommodations, but if it takes 45 flying hours, eight layovers, and an additional bus/train once on the ground to actually get there, your team probably isn’t going to be in a great mood.

More specifically for this trip, we wanted to answer the following questions:

  • How are we getting to the area?
    • What’s the best (cost-wise and time-wise) way to get everyone to Scotland?
    • What are customs like?
  • How are we getting to the venue?
    • Once in Scotland, do we need to take a train or a bus to get to Dunskey?
    • If so, what is that train/bus like? Are any amenities included?
  • What does the travel feel like?
    • Most team members will be switching time zones. How does the jet lag feel?

When evaluating travel, particularly if you are yourself a frequent traveler: try and put yourself in the shoes of someone who rarely, or never, travels. Every time I found myself thinking, “well, that’s not great but it’s doable,” I’d make a note.

Riding the rails is charming, but turned out not to be right for our team.

For example, on paper it looked a lot cheaper, though slightly longer, to have our team fly into London and then take the train up to Dumfries in Scotland. Though tempting in order to save on travel costs, when I actually tried out the route I found it to be cumbersome and exhausting. If I, someone who travels dozens of times per year, felt like something was merely tolerable, it’s likely a team member who doesn’t enjoy travel might find it horrifying. My notes on this area were very helpful upon return, and made our decision to choose the more convenient but slightly more expensive route for the rest of the team a lot easier.

Accommodations

What’s it like to stay there?

We wanted to be particularly mindful of not simply comparing/contrasting this accommodation to places we had previously hosted SkyTrips. Part of the fun of these retreats is getting to experience something new and different with your team! Each new retreat should stand on its own. That said, we have some basic requirements for our accommodations. To make sure Dunskey would meet those, I focused on the following questions:

  • How comfortable is it?
    • Are the bedrooms/bathrooms good quality? Do they provide ample private space for each team member?
    • Are there toiletries provided or will we need to supply our own?
    • What are meals like? Will we eat out at restaurants or will they be catered? What food options exist and how does the food taste? What about snacks/drinks in between meals?
  • What will it be like to work from the venue?
    • Is there a big enough space for all of us to spread out with our laptops?
    • Is there a room or area that’s good for hosting our large group sessions?
    • What is the internet like? Is it fast enough to support our work? Is there coverage throughout the venue? If not, is there a suitable backup option, like relying on a hot spot?
  • What is the overall vibe of the venue?
    • What does it feel like to stay there?
    • What different types of gathering spaces are there?

I was very lucky to able to spend a weekend at Dunskey with Anne and Ali, the most gracious owners and hosts. This length of time was ideal to relax into the experience, and take plenty of notes on everything. They even hosted a small dinner party with a few of their friends so I could experience the delicious creations of their in-house chef!

Post-dinner photo; I was way too excited and forgot to take a photo prior to our delicious meal!

If you’re not able to stay at least a couple days/nights at your location, ask the owner if they’re willing to let you spend at least a morning or afternoon. Doing a guided tour with questions you’ve prepped ahead of time is a great way to get a quick run-down, and wandering around on your own for a bit (test wifi speeds in different areas, walk the grounds, etc.) is also a good way to get a sense of the overall vibe.

Activities

What should we do while there?

Finally, you’ll want to evaluate all of the potential things you could do as a team together while there. We have a general rule of thumb to default to more free time rather than too much structure for our team retreats. As a remote team, we’re essentially fitting a year’s worth of coffee chats, watercooler run-ins, and team dinners into one week. We’ve found the best way to let that happen is by simply… letting it happen. Getting out of your own way and letting your team dictate the majority of their time leads to better things than you could ever plan!

That said, of course we plan some things. So I also kept the following questions in mind:

  • What’s the surrounding area like?
    • Do we want to spend most of our time on-site or are there nearby attractions, activities, or sights that we shouldn’t miss?
    • Is a day trip to somewhere nearby a good use of our time?
  • Are there activities offered by Dunskey, or do we need to organize our own?
    • If they do offer activities, what are those like?
  • What sorts of things will the team need to pack?
    • Do any of our activities require specific clothing or shoes?
    • What can we expect in terms of weather?


The sleepy little town where Dunskey is located. There’s not much to do here, but with 2,000 acres and plenty of onsite activities, we won’t get bored!

Part of the reason we narrowed in on Dunskey was the exceptional food and activity options that came along with the accommodation. Before selecting one (or several if you’re swanky!) location(s) for a scouting trip, be sure to ask if they have food and beverage, and/or activity brochures. Having done this, I was able to seamlessly envision our team enjoying a beach BBQ, racing through the hedge maze, going for a walk into town, etc.

If your accommodation doesn’t offer their own food/activities, I recommend doing some quick research into the surrounding area and making a top five list of potential restaurants/activities. That way, you can try those out while on your trip and bring back notes on which ones you think will work best for the actual retreat. (And when in doubt: ask the locals for recommendations for places to try!)

In sum…

Have fun! Scouting trips are an absolute joy. The more you prepare ahead of time, and the more notes you take while on the trip, the easier it is to communicate your findings to the rest of your decision-makers and align on a final location selection.

We’ve found the above framework and questions to be right for our team, but you’ll likely have different needs and questions to answer. Regardless of what the specific questions are, the important piece is actually getting to the location and evaluating it in person. As far as we’ve come in the digital era, there’s still no replacement for experiencing a place in real time. Questions? Scouting trip stories of your own? I’d love to hear them! Leave a comment below, and stay tuned for the next post in our series–location selection!

Cheers from Dunskey!
Catherine Scallen
Catherine Scallen is Jilt's Head of People. She makes sure everything runs smoothly, from HR to travel planning to onboarding. When not ops-managing, she has a penchant for putting googly eyes on inanimate objects and finding hidden wisdom in children's books.

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