Great Companies Make It Easy for Customers
Leadership Lessons from Broken Experiences in Retail, Tech, and Transportation
In my 30 years of hospitality and service leadership, one lesson has never failed: the best companies make life easier for their customers. When we build seamless experiences, we show that we respect people’s time and energy. Recently, I experienced three frustrating service failures that reminded me how easy it is for even successful organizations to let the customer experience slip. But these aren’t just stories of poor service—they’re opportunities to ask ourselves: Are we truly making things easy for the people we serve?
When companies work together, break down silos, and lead with purpose, they can prevent these issues from ever reaching their customers.
1. A Target Order That Became My Wife’s Problem to Solve
After a recent move, my wife placed an online order with Target but forgot to update our shipping address. She realized the mistake immediately and tried to correct it—but the app wouldn’t allow any changes. Customer service told her it was too early in the process to adjust the order—and too late to cancel it. They advised her to call back the next day.
And so began a frustrating cycle. She called again and was told to wait for a tracking number. When the tracking number came, she called again—and was told the system hadn’t yet received the update. Seven calls later, and countless explanations of the same issue, the package was ultimately delivered to the wrong address. Thankfully, someone finally recognized the ridiculousness of the situation and issued a refund—but only after the system had completely failed her.
Where was the company working together to solve the problem? Where was the empowerment to fix a simple issue before it turned into a customer nightmare?
2. HP’s Order Process: A Masterclass in Disconnection
I ordered a new laptop from HP.com on June 6 with expedited shipping—I needed it quickly to replace a malfunctioning HP device. What followed was weeks of missed deadlines, conflicting updates, and unanswered questions.
I was told repeatedly that the laptop would arrive “that day,” even though no tracking number ever appeared. When I tried to cancel the order, I was told it was “too far along”—yet no one could confirm whether it had actually shipped.
Despite emails and even a LinkedIn message to HP’s CEO (which received no reply), it took until June 30—24 days later—for the laptop to finally arrive. Ironically, I received a shipment notification after the first delivery attempt had already been made.
This wasn’t a technology problem—it was a leadership one. Where was the company alignment on what the customer experience should be? Where was the shared ownership of fixing the breakdowns before they reached the customer?
3. A Simple Wing Order Made Needlessly Confusing
Dining out should be easy. My son and I both ordered 10 chicken wings with two flavors each—five wings of each flavor. When our food arrived, it was served on four plates of five wings each, but no one could tell us which plate was whose. The person delivering the food hadn’t taken the order and had no idea.
He admitted as much, saying, “I’m not sure.” I appreciated his honesty, but no one took ownership to solve the problem. We had to taste the wings ourselves to figure it out—and frankly, we never were really sure.
This wasn’t a matter of flavor confusion—it was a missed opportunity for someone to say, “Let me find out for you.”
How This Applies to Transportation
In transportation, our goal should be simple: make the journey seamless. Customers should never have to work hard to book a trip, understand a schedule, solve a problem, or enjoy the ride. Here’s what these experiences remind us:
• Processes and automation should never replace people’s ability to help. Target’s system was so rigid that no one could step in to fix an obvious mistake. In transportation, we must balance automation with human flexibility—empowering our companies to resolve issues quickly.
• Leaders must experience their own services. HP’s leadership clearly hadn’t walked through their own ordering process. Transportation leaders should regularly book a trip, take a ride on their own service, or file a complaint—and then ask, “Would I accept this as a customer?”
• Customization without clarity fails the customer. The restaurant offered choice but failed to deliver clarity. In transportation, if we offer vehicle options, routing flexibility, or premium services, we must ensure those choices are executed flawlessly and explained clearly.
And finally, when a problem surfaces, own it. Don’t pass the issue along. Work together to solve it, quickly and completely.
The Leadership Challenge
Leadership isn’t about blaming systems, blaming staff, or blaming the customer. It’s about saying, “We’re better than this, and we can fix it together.”
So, ask yourself and your company:
- Are we making our customers’ experience easy?
- Do our processes work for people, or against them?
- Have we walked in our customers’ shoes recently?
Great companies don’t get there by chance—they build cultures where companies take ownership of the customer experience. They remove friction, empower their people, and work together to solve problems before they happen.
That’s how we make the ride—or the order, or the dinner—effortless.
Together, let’s do better.
Featured photo: “Peter Pan all hands on deck for holiday travel” by Peter Pan Bus Lines
Brian Dickson is the owner of Bus Business Consultants and author of Ground Transportation Insights on Substack. Drawing on leadership roles in motorcoach operations and Disney’s Guest Transportation, he helps operators improve performance, culture, and growth—Bus Business Consultants: Driving Performance, Culture, & Growth in Ground Transportation.
This article was originally published on August 20, 2025 at Ground Transportation Insights.
