Deep in the heart of Texas

Wildbit has a stellar tradition of team retreats as the one time a year we get together in person. Over 18 years of business, Wildbit developed from 100% remote to mostly remote where the majority of the team is currently scattered around the world and some of the crew is in Philadelphia. Retreats are crucial for reflecting, planning, and letting loose together. We’ve been fortunate to have such a great team that the retreat is met with excitement and enthusiasm as opposed to a dreaded business travel requirement. (That’s not just talk — Natalie will literally run through the airport to greet the team!) With all the anticipation comes a good amount of pressure to make it a valuable and memorable trip for everyone. While the “Team Happiness” component of my role encompasses many things throughout the year, retreat planning and execution is top of the list.

My first day at Wildbit was heading to retreat in April 2017. My goal was to learn as much as I could about the experience and help out as much as possible. I was in the thick of it but didn’t have to do any of the planning. I knew it was such a big undertaking that I started researching for retreat 2018 as soon as we got back from Florida.

I started by reading blogs of other people’s endeavors — first with the Wildbit team in Orlando 2016, Dominican Republic 2013, and Spain 2011. I also found great information from Balsamiq, EventMobi, and Buffer on how they maneuvered through the decision-making and planning steps of a team retreat. After collecting some guidance (and ego-boosting that I can do this!) I reached out to the team for dates of travel that were a hard “no” for them. Fortunately we didn’t run into major conflicts and had about 3 weeks we could work with for scheduling. This felt good since we would have a little flexibility if we chose a location that was in high demand. I also gathered details on dietary accommodations and flight preferences from everyone so I could account for any special needs.

The initial phase of searching for a location began in May 2017. I was given wide open discretion on locations and found out pretty quickly the world is a big place! The one thing that helped limit my options was ignoring places that would have forced grueling travel for anyone on our team (sorry, Australia!). 30+ hours one way is too much for us to ask for a 5 or 6-day work trip.

The “need to have” guidelines were: excellent wifi, private use of property, 27 beds in at least 13 rooms, and on budget.

“Nice to have”: stay in as few houses as possible, within a 2 hour drive from an international airport, activities for the team, and a space for all of us to meet and have meals together.

The first issue I ran into was finding a house big enough for the right price. Sure, there are castles in France but not realistically affordable for our trip. The homes that boasted “sleeps 50” really meant 2 people to a bed, 3 pull out couches, and the “kids” room with 8 bunk beds. There’s some really stunning homes out there but not an obvious fit for us. We weren’t interested in hotels because we wouldn’t have the group privacy we needed to have meetings in casual settings where we could come and go as we please. We also wouldn’t want the team to only have the option of board room, pool, or hotel room as the meetup spots for the week. By having free rein in our lodging location, we don’t have to coordinate time and place with an event planner or worry about competing with other guests for the use of amenities. I started with private rentals then branched into resorts, luxury villas, and even hostels in several countries. We did narrow down the search to U.S. only but kept running into the same concerns. After 4 months, I compiled a list of about 20 locations but none of them felt solid — there was something with each of them that wasn’t the whole package from our standpoint.

By September 2017, I had reached out to a few different companies that market their properties to “digital nomads”, a few luxury property rental groups, and an organization that solely coordinated company retreats. I was also introduced to Justin at Helmsbriscoe through my friend that had used his services for her local company meetings. I originally felt that our needs and his expertise were in different spaces but it was worth a shot. A week later he came back with a list of a dozen solid options, including our final choice: JL Bar Ranch & Resort.

Once the contracts were signed, we announced the trip to the team in a teaser video.

Aside from the obvious beauty of the resort, there were some unique offerings in their proposal that made them stand out:

1. We would have the entire resort to ourselves.
2. There is a full staff on hand.
3. They could sleep the whole team comfortably.
4. The proposal was in our budget.

Resort to ourselves

Wildbit retreats in the past have been more geared towards large homes, comfortably fitting as many people as possible under as few roofs as possible. This gives us privacy and the ability to run the show — we’re not on anyone else’s schedule or tiptoeing around other guests. This also forces allows loads of quality face-time with one another. The casual intimacy of being in a home has served the team well for many years. However, with the team growing, we needed to consider an alternate setup.

The main lodge had plenty of space for our whole team to meet regularly. We brought a bunch of couches and chairs to one spot and it became our home base for the week. There was also a good 5 or 6 spots that we could break out into smaller groups without interrupting each other. Having the place to ourselves was amazing — we didn’t need to worry about rearranging the furniture each time we had a meeting or worry about leaving our belongings laying around. We didn’t have to be limited to a conference room for the confidential business decisions or edit our conversations around the property. It was very easy to make ourselves at home in this space.

Full staff

This was something that was (selfishly) very attractive to me. I spent the majority of my first retreat shopping, cooking, cleaning, and facilitating logistics for the group of 26. And that was part of a two-person team. I was honestly nervous being solely responsible for all those things for a week. It can also wear on a person when you’re trying to get quality time with everyone but are pulled in the direction of “host” as opposed to “guest.” Mind you, I know the team would chip in if asked but I also felt it was my goal to allow everyone to enjoy their time together as much as possible. While it seemed great in concept to have a full staff on hand, there is also the question “Will they deliver?” Unfortunately, relying on other people to bring their A-game can sometimes leave you disappointed and worse off than if you just did it yourself.

Another concern was relying on their crew to meet the dietary needs of the team. We were going to a ranch, in TEXAS, with a handful of vegetarians and vegans. There were also gluten-free and other considerations in play so we didn’t want to mess around with getting everyone fed. While shopping for and cooking our own meals in the past did take a chunk of time, it also let us control our needs and offer some built-in team bonding. We also have a pack of coffee connoisseurs and I know they were used to having freedom in a kitchen to make their brew. What seemed obvious at first had me questioning if the payoff would be worth the adjustments.

I cannot express enough how incredible, thorough, kind, and attentive the team at JL Bar and Resort was. (SouthernHospitality × Professionalism)³! Lana and I started emailing in March to nail down logistics, dietary restrictions, requests, and expectations. I may have been over-detailed in many aspects but she was right there with me, providing answers and asking great questions for things I did not think of.

As we got closer to the trip, our emails turned to texting and she certainly saved me from nightmares of ridiculous things going wrong. Once we arrived, the entire staff was on point. I mean, we had a personal escort from the highway guide our bus to the gates at 1am! The food and beverage staff, along with resort managers and the housekeeping team, made a valuable difference in the flow of the trip. They gave us space to make ourselves at home and were readily available to handle our requests. Breakfast, lunch, and dinner were thoughtfully coordinated in a separate space from our meeting spots. Meals were ready on our schedule and we didn’t have to worry about prep, cleanup, or interference with our next session.

Sleeping Arrangements

As mentioned before, we needed 27 beds spread out between at least 13 rooms. There was more than enough rooms and beds at JL Bar so we were golden on that front. However, without holding the team captive, we don’t want to provide too much space for people to wander. The whole point of retreat is to have quality and productive time together and sometimes outside distractions need to be removed to encourage that flow. We weren’t certain what to expect with this hotel-like setup of 16 bedrooms/bathrooms split between 8 cabins but it seemed to be a valid option versus the roadblocks of other properties.

Based on the interactions that week and feedback from the team, it turned out to be a solid balance of collaboration space and just enough privacy for a nap or to decompress for a little in between gatherings. We were quite literally in the middle of nowhere so there wasn’t much of an interest to leave the lodge. Also, when getting a group of friends together once a year, there can be some late nights of games, karaoke, and dips in the pool. The spacing of the cabins allowed for the early birds to peacefully drift off while the night owls did their thing without being hushed.

Budget

We started planning for the retreat based on the numbers of last year’s trip — about $45,000. This covers all costs for the entire team: flights, lodging, meals, drinks, activities, ground transportation, and the miscellaneous items that pop up (shipping items to retreat in advance, snacks/meals during travel, etc.) In my preliminary searches, the properties in that range weren’t good options and the places that were good options were over $100,000. If I came across a home that hit the budget, then the flights turned out to be the thing that put us over. I came from the mindset that even if the numbers seem to line up, it’s going to be more expensive than less.

I shared our numbers with Justin and I honestly thought it was a mistake that JL Bar was in our range. Chris and Natalie looked at the summary and thought the same thing themselves. Once I started hashing out the flights, I knew we were going to be over $45k but we all agreed it felt good to go this route. We also had one more team member (27) than the year before and one more night on the trip so that accounted for some of the higher costs.

Since the ranch was about 3 hours from the closest international airport (San Antonio), our trip ultimately consisted of five nights at JL Bar and one night at the Hilton near the airport. This allowed everyone to get to the airport as needed for their travels home, especially since the majority of the team selected early morning flights.

All said and done, the 2018 retreat cost us:

• Food and Beverage * = $16,656
• Lodging * = $15,427
• Ground Transportation * = $4,169
• Flights = $15,697
• Everything else = $1,073 (tips,activities, items purchased and shipped in advance, meal reimbursements at airport)
• Total = $53,022 or $1,963/person

* HelmsBriscoe reported that they saved us over $10,000 through their contracted discounts with their travel partners

As one can expect, there were some things that didn’t go perfectly:

• The flight from Philly to San Antonio was delayed a few hours so the majority of the team was left waiting at the airport since we had one bus to take us all to the resort. Plus the 3-hour ride made for a very late and long day of travel.
• Texas in June is H-O-T. The pool was refreshing and the AC was pumping but it was tough being outside in the sun.
• When you’re in the wilderness, there’s actually wildlife. We heard and saw a few rattlesnakes that left some folks… rattled?
• The AC on the bus ride from the resort to the airport hotel broke as soon as we got rolling. It was a very hot and quiet 3-hours.
• Our check-in and dinner shuttle arrangements at the Hilton were not handled as promised and left us waiting around while they rushed to accommodate our group.

Another one for the books! I can’t believe it’s over and I’m already getting into Retreat 2019. Where should we go?