Sometimes the breakthrough isn’t a better answer.
It’s a better question.
As I looked back at the four articles published in September, that idea kept showing up in very different ways.
When considering artificial intelligence, the question isn’t simply, How can we use AI? It’s What problem are we trying to solve?
When planning for the year ahead, the question isn’t simply, What can we afford? It’s Where are we trying to go, and what will it take to get there?
When trying to turn around a struggling business, the question isn’t simply, How do we generate more revenue? It’s Are we generating profitable revenue?
And when performance isn’t where we want it to be, the answer isn’t always more effort, more oversight, or another process. Sometimes we need to ask, What might already be getting in the way?
Different subjects.
Same leadership lesson.
Better results often begin with better questions.
If you missed one, here’s a look back at September.
The More Artificial Intelligence We Have, the More Human Intelligence Matters
Artificial intelligence is creating enormous interest across the ground transportation industry.
But the wrong place to start may be AI itself.
In this expanded version of an article originally published in Busline Magazine, I explored how transportation operators are beginning to use AI and why I believe the most productive approach starts somewhere else:
Start with the work.
What problem are you trying to solve?
What task consumes too much time?
Where could better information improve a decision?
Where are people doing repetitive work that technology might help simplify?
From there, determine whether AI is actually the right tool.
And as these tools become more capable, something else becomes increasingly important: human judgment.
AI can process information, identify patterns, summarize data, and accelerate work.
But leaders still have to ask the right questions, challenge the output, understand context, and decide what to do with the information.
The more artificial intelligence we have, the more human intelligence matters.
Don’t Wait Until January to Plan for 2027
Too many organizations wait until the end of the year to begin thinking seriously about the next one.
By then, budgets may already be taking shape and resources may be starting to be allocated.
I believe we should reverse the sequence.
Strategy should help create the budget—not become something leaders discuss after the budget has already determined what the organization can do.
That means beginning with fundamental questions.
Where are we today?
Where are we trying to go?
What are the few priorities that will make the greatest difference?
Who owns them?
What needs to happen next?
And how will we know whether we’re making progress?
Strategic planning doesn’t need to result in a complicated document that sits on a shelf.
It should create clarity, establish priorities, assign ownership, and build an accountability rhythm that turns intentions into action.
And if you’re waiting until January to start thinking about next year, you’re probably already late.
It Has to Make Money
The final installment of the Minnie Van Leadership Case Study brought the story back to one deceptively simple requirement:
It has to make money.
The first three installments explored how a service that guests loved could still struggle financially, how we discovered that the underlying operating model—not demand—was the real problem, and how nearly two years of uncertainty gave us an opportunity to rethink the business.
The final chapter was about execution.
We became clearer about the customer we served and the value we provided. We reconsidered pricing. We aligned capacity more closely with demand. We established boundaries around what the business should—and shouldn’t—do. And we continued measuring, learning, and adjusting as the service returned.
The result was a nearly $4 million financial turnaround, approximately 40% revenue growth, and a shift in operating margin from roughly -28% to +13%. Pasted markdown (3)
But the larger lesson wasn’t simply about Minnie Van.
Growth doesn’t automatically create a healthy business.
Revenue isn’t necessarily profitable revenue.
And sometimes the most important question isn’t: How do we grow?
It’s Does the business model underneath that growth actually work?
Stop Throwing So Hard
What Sandy Koufax, Norm Sherry, and a different point of view can teach us about performance
Sometimes we’re so close to a problem that our instinct is simply to try harder.
Add another process.
Create another report.
Schedule another meeting.
Increase oversight.
Provide more training.
But more isn’t always the answer.
Stop Throwing So Hard begins with the story of Sandy Koufax and catcher Norm Sherry. Koufax had extraordinary talent but struggled with control. Sherry offered a remarkably simple suggestion: stop trying to throw every pitch so hard.
That different perspective helped unlock the ability Koufax already possessed. Pasted markdown
It reminded me of a problem I encountered years later in Disney’s parking operation. A seating process created for trams without doors remained in place for years after doors had been installed—even though the original reason for the process no longer existed. Pasted markdown
Nobody was doing anything irrational.
We had simply become accustomed to the way things worked.
Sometimes performance improves not because we add something new, but because someone asks a question that causes us to see something familiar differently.
The September Throughline
Four articles.
Artificial intelligence.
Strategic planning.
A transportation turnaround.
And one of baseball’s greatest pitchers.
On the surface, there’s very little connecting them.
But underneath, each was essentially the same leadership challenge.
Are we solving the right problem?
That’s a question I’ve learned to appreciate more as my career has progressed.
Leaders are often rewarded for having answers.
But some of the most important moments in my career began when I realized I didn’t yet understand the problem well enough to have one.
Sometimes we need to question the tool we’re excited about.
Sometimes we need to challenge the sequence we’ve always followed.
Sometimes we need to reconsider the assumptions underneath a business model.
And sometimes we need someone with a different perspective to point out something that’s been sitting directly in front of us.
Experience matters.
Data matters.
Technology matters.
Effort matters.
But none of them guarantees we’re solving the right problem.
Before looking for another answer, perhaps the better leadership discipline is to stop and ask:
Are we asking the right question?
Looking Ahead to October
October will mark a milestone for Ground Transportation Insights:
The 100th edition.
When I started GTI, the goal was simple: share lessons from my experience leading transportation operations and organizations while sparking conversations about leadership, culture, performance, and the challenges facing our industry.
It seems fitting that article #100 returns to a subject that has shaped much of my career.
Hospitality Is a Leadership Decision
Every transportation company moves people from one place to another.
The best transportation companies do something more.
They create an experience people remember.
In October, I’ll explore why transportation companies are also hospitality businesses—and why the experience customers receive isn’t simply the responsibility of the employee standing at the vehicle door.
It’s a leadership decision.
We’ll also explore another side of organizational culture in:
The Right of Way Isn’t Always the Right Decision
Policies and procedures matter.
But no rulebook can anticipate every situation employees will encounter.
What happens when someone technically follows the rule but still makes the wrong decision?
This article explores the role culture plays in providing the framework employees use to exercise judgment—and why an organization’s real values often become clearest when following them becomes inconvenient.
I’m looking forward to sharing both.
And I’m especially grateful to everyone who has helped Ground Transportation Insights reach 100 editions by reading, subscribing, commenting, sharing, and joining the conversation along the way.
A Closing Thought
One hundred articles is enough to notice a pattern.
The most valuable leadership lessons are rarely complicated.
Ask better questions.
Understand the business.
Challenge assumptions.
Listen to people with different perspectives.
Know where you’re trying to go.
Measure what matters.
And remain willing to change your mind when the evidence tells you something you didn’t expect.
Those principles have appeared repeatedly throughout Ground Transportation Insights because they’ve appeared repeatedly throughout my career.
The situations change.
The questions change.
But curiosity remains one of a leader’s most valuable tools.
Because sometimes the answer we’ve been looking for isn’t particularly complicated.
We just haven’t asked the question that reveals it yet.
Question for readers: What’s one question that changed the way you looked at a problem in your organization?
If your organization is working through questions around leadership, strategy, operational performance, or sustainable growth, I’d be happy to help.
Through coaching, advisory support, consulting, and fractional leadership engagements, I work with transportation organizations to better understand the challenges they’re facing, identify the right priorities, and turn those priorities into measurable results.
Learn more at Bus Business Consultants.