How I Cross-Trained My Way to a Career

You’re reading this article because I worked at The Great Movie Ride in 2004.

Let me explain.

I began my Disney career as a part-time attraction host. I was an Ops / HR manager for another company and looking for something fun to do on the weekends. Most people would get a hobby. I got a second job … at Disney World!

It only took two months for me to realize I wanted to make Disney my full-time career. I was totally sold on the “magic” (which is 100% real, by the way). But there was a problem. I had zero tenure at a company that promotes heavily from within. My upwardly-mobile peers had already been there full-time for 5, 10, even 15 years. My management background wasn't going to be enough. I had to find a way to show people I was ready to step up here, even if I was still “earning my ears".

To that point, I worked in one location: Star Tours. But there were other locations in my area, including:

I had to be cross-trained at a location to work there. This would also open opportunities to serve as a peer trainer and coordinator, building experience that supported my path toward management.

I did some research and discovered that only a small number of cast members worked in multiple locations. They were usually the ones working toward promotion. Managers noticed them more often because they could leverage their skills to fill staffing gaps and run the operation with greater agility.

That became my plan. I would cross-train my way into a manager position at the Walt Disney World Resort. If I could become the most skilled, most flexible, and most indispensable member of the team, I would be the obvious choice for promotion. Right?

First, I made a list of every possible designation I could earn in my area. I taped this handwritten list to my refrigerator. It looked something like …

Twelve unique positions stood between me and my goal: guest experience manager.

Next, I had to figure out how to get myself on the training schedule as quickly as possible. No one in the area had cross-trained in every role, so I didn’t quite know where to start. There were also rules I had to consider. For example, cast members were required to be in their current role for at least six months before training in a new position. I had only been with the company for three months. Plus, I had a full-time job, so my availability was limited.

I did the math. If I waited for things to progress on their own, it would take at least two years to reach my goal. I wasn’t willing to wait.

So I launched an influence campaign. I looked for people who could help me overcome these obstacles for mutual benefit. Think of  it as networking — with purpose. I quickly discovered that the training coordinator for one of my target locations was married to one of my managers. So I made sure he noticed me every time we worked together. I took on extra tasks. I volunteered to cover shifts. I came in early and stayed late. I was the perfect team member. After a few weeks, I happened to mention my interest in working at other locations. Within days, I was on the training schedule.

The rule said I had to wait six months. I checked my first cross-training box in four. Networking!

I ramped up my influencing efforts. I spent my breaks speaking with experienced cast members, picking up additional insights. I re-read SOPs to make sure I understood the ins and outs of every attraction. I used every second on the clock to improve my ability to do the job. 

I also opened my schedule. I typically worked closing shifts in my manager gig, so I made myself available for opening shifts as well as weekends. I picked up as many hours as I could and quickly became a regular presence in the area. On average, I worked nine days (shifts) and drove 515 miles per week. 

Sure, I was tired all the time. I barely had a life outside of work. But I was making fast progress. I checked my first box in November and completed the list by the following August. In 10 months, I completed 12 training programs and became the “most capable” person in the area. 

I interviewed for a manager role that October, was added to the talent pool in December, and transitioned into a full-time position two months later.

Looking back years later, I’m confident I would have eventually been promoted. But it would have taken another year or two. At that point, the delay would have tested my patience. Now I see that it would have altered the course of my entire career.

I would have missed the opportunity to join the training team for a major guest service initiative. I would not have become an L&D manager. I would not have made the connection that led to my next role outside the company. I would have missed the chance to experiment and sharpen my point of view, which ultimately led me to writing and speaking activities. I might never have written my books or transitioned into technology. And you probably would not be reading this.

The moral of my story is simple: the more you can do, the more opportunities you unlock. I’m a firm believer in the value of generalists. Sure, specialities are important. But in real life, a wide range of skills provides the flexibility needed to adapt to unexpected situations — like a global health crisis or the AI-enabled transformation of the workplace.

My story demonstrates why skill development must be an organizational priority. Careers are shaped by opportunity, and opportunity favors people who are prepared. Organizations that fail to prioritize development limit both individual potential and business agility. 

The lesson applies far beyond Disney. Work changes faster than job titles. Roles blur. Needs shift. The people who advance are often the ones who can contribute in more ways, solve more problems, and adapt without waiting for permission. This only happens when development is designed to keep pace with reality.

This is also why L&D must evolve. Our job is not to design and deliver training programs. We must architect systems that help people grow continuously through cross-training, applied experience, accessible resources, and real-world practice. When organizations invest in this kind of enablement, they create talent pools that are resilient, mobile, and ready for whatever comes next.

This approach shaped my career and changed my life. It can do the same for you too.

Thank you for everything you do. Let me know how I can help. Be well. JD

AI Statement: Every word in this post was written by the human author. AI was used to support research, ideation and editing throughout the creation process.