Winter Trees in Orlando?

Why this matters

Winter Trees in Orlando is a story about what holds us up when everything around us is in motion. Titles shift, key leaders disappear, and the pressure only grows—but the roots and branches of a strong team can still keep us standing. This matters because many of us lead through “winter” seasons while pretending it’s still summer. When we name our supports, share the load, and trust our people, we discover that resilience is almost never a solo act.

An Odd Pairing

Orlando is known for sunshine and color, not soft winter hues and bare trees. So how do these two things relate? Now that is an interesting yarn.

After 30 months as the hotel manager at the 44th largest hotel complex in the world, the general manager who hired me left the company in October. A six‑month search for his replacement began. The vacuum sparked internal politicking and plenty of maneuvering.

This alone was a story of resilience and fortitude. In the very first meeting after his departure, a politically savvy peer slid into the general manager’s chair at the conference table. That said it all.

Even with all the positioning, I was recognized as the acting general manager—part of a deeply experienced, high‑performing executive committee, with ownership representatives housed on property. With so many talented peers leading their areas, my role was to keep the executive committee united and focused. I had the accountability—but not always the direct responsibility—for making sure the resort’s performance stayed where it needed to be.

A December to Remember

December is the busiest time of year for the happiest place on earth. At this resort, December is its own season, with the highest room rates and occupancies. The season “ends” on January 1, when the hotel finally empties and everyone can breathe.

To add some spice, by early December the rooms division director left the company. The assistant rooms director was on a prolonged leave of absence. One front office director would miss the busiest season due to paternity leave, and the other front office director wasn’t starting until December 26. The rooms division leadership was significantly thinned out—three levels below my position.

As I planned for the holiday season, I learned that on January 2 we would host a once‑in‑a‑decade group arrival. Our resort had 2,300 rooms in two hotels. On that single day, we would welcome 6,000 guests: 4,500 guests on 94 buses arriving in a three‑hour window, and another 1,500 arriving on their own.

On the bright side, housekeeping and laundry had New Year’s Day to clean all 2,300 departing rooms and turn all the linen for the January 2 arrivals.

A Reminder That We Are Never Truly Alone

I felt the impact of the vacant positions above and below me. But I chose to remember that this resort was “ideally positioned between wonder and wonderful.” The rooms team would rise to the occasion.

Winter Trees Knot Art is my testament to the strength I found in that community. Even in the harshest winter, the support of those around us gives us the grounding to stay standing. Each knot is a connection made, a moment from that arrival we all experienced and shared, and a reminder that we are never truly alone.

Every department stepped in. Sales managers and event managers helped register and welcome guests. Engineers met buses. Security led the arrival parking plan for 94 buses.

Plan the Work & Work the Plan

Managers below director level worked directly with me, showing their expertise and helping design plans to:

• make 6,000 keys,

• stretch our less‑than‑ideal linen inventories (that’s another yarn),

• turn departing rooms as quickly as possible, and

• keep chaos from ruling the day.

With 6,000 guests and 1,800 colleagues, a little chaos was expected. But it was controlled chaos.

A Tour of Wonderland

One of my favorite memories is walking into the back office of the front desk at our 850‑room hotel and seeing one of my managers sitting on the floor, surrounded by keys. I didn’t know what had happened, and I didn’t ask. Showing up as the hotel manager with negative energy wasn’t going to solve anything.

Instead, I asked myself, “What can I do to impact this situation?”

To buy time, I went to the satellite registration area in the ballroom, got the attention of the hundreds of waiting students and guests, and asked, “Who wants to go on a tour of the resort?” I must have looked like the Pied Piper, leading more than 100 people around the grounds for 40 minutes. By the time we returned, the key issue was resolved.

Lessons in Community

This experience taught me that even in the harshest winters, roots run deep. Roots are your frontline managers and direct reports. Giving them responsibility and encouragement is how you grow lush experiences.

Branches stabilize you—these are your peers. When you’re connected, the wind won’t take you down.

And the trunk? That’s your shared plan. Have a documented plan for major arrivals as early as possible. Review it, refine it, and then enjoy the pure joy and beauty of a truly collaborative team effort.