Ground Transportation Insights

Ground Transportation Insights

Leadership Topics

The Real Problem Wasn't What We Thought

Everyone was looking for better answers. The breakthrough came when we started asking better questions.

Brian Dickson's avatar
Brian Dickson
Jul 15, 2026
∙ Paid
Behind the recognizable vehicles was a business model that, despite strong guest demand, faced significant operational and financial challenges.

Part 2 of a Leadership Case Study Series

In Part 1, I shared how I assumed responsibility for Minnie Van just months before COVID shut down Walt Disney World.

As I immersed myself in the operation—training as a driver and shadowing the dispatchers and managers, it became clear that the challenges facing the business ran much deeper than guest demand.

At the end of that article, I shared the realization that changed everything.

The issue wasn’t demand.

The issue was the operating model supporting the demand.

Once I reached that conclusion, the obvious next question became:

If demand wasn’t the problem... what was?

My first instinct wasn’t to start changing things.

It was to understand why the business had arrived where it was.

That meant studying more than the operation itself.

It meant studying the decisions that had shaped it.

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Smart People Had Already Been Working the Problem

One thing surprised me almost immediately.

This wasn’t an operation that had been ignored.

Quite the opposite.

Over the previous two and a half years, finance teams had analyzed it.

Industrial engineers had analyzed it.

Operational leaders had analyzed it.

Changes had already been made.

The business wasn’t standing still.

Yet, despite all of that effort, the operation continued to struggle financially.

What struck me wasn’t that people hadn’t cared.

They absolutely had.

Intelligent people had invested countless hours trying to improve the business. They had studied demand, analyzed costs, modeled scenarios, and implemented changes. Every recommendation had been made with the best of intentions.

That’s an important leadership lesson in itself.

Struggling organizations are rarely struggling because nobody is trying.

More often, they’re struggling because everyone is working hard to solve the same problem from the same set of assumptions.

Then a different thought occurred to me.

Everyone was looking for better answers.

The breakthrough came when we started asking better questions.

That led me to one question I couldn’t shake.

What if the answers we’d been finding were perfectly logical...

...but they were answers to the wrong question?

That became the turning point.

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