From the October 2025 issue Leadership

Two Things Leaders Can Do When Business Strategy & Client Needs Clash

If you’re a business owner, executive, or manager, here’s a hard truth. Just because you aren’t hearing negative feedback, it doesn’t mean you’re doing a great job.

It might mean your customers are tired of hopping through hoops to get heard and have given up trying. It might also mean your employees have stopped caring or they feel their efforts to affect change are futile against systems that insulate you and other leaders from what you need most, the truth. Your problems aren’t gone—they’re just hidden underground and waiting.

Remember that pain is never too great for people who don’t have to feel it.

I was reminded of that while watching an old Joe Pesci movie called The Super. It was based on a real New York City landlord, Morris Gross, who racked up over 400 housing code violations and was sentenced to live in one of his neglected buildings. In the film, Pesci’s character was forced to live under house arrest in one of his rundown properties. He became both tenant and superintendent.

Think about that. He was made a customer of his own property management company and a frontline employee at the same time.

That movie delivered a lesson every business leader should take to heart. When you don’t feel the pain your customers or employees feel, it’s easy to underestimate how bad it really is. And when you’re the one causing it, whether through policies, pricing, or plain neglect, there needs to be a greater sense of urgency to fix things.

The movie was one thing. But I also saw this play out in real life recently, twice.

The first time was at a four-star hotel in Las Vegas. I checked in, bags in hand, ready to relax—until I was hit with a mandatory $56 resort fee. I asked what it covered: a landline phone (which I’d never use), access to the gym (I’d already exercised), and use of the pool—from 9 a.m. to 5 p.m.

I felt manipulated, but moving to another hotel meant more hassle, fees, and headaches. So I paid the $56—not for value, but for convenience. I hoped things would get better. They didn’t.

It was 4:41 p.m. The pool was basically a non-option. Checkout was at 11 a.m., so the window for actually using the amenity I paid for was about an hour the next morning.

The next morning, I trekked to the pool, only to be stopped by security. The room key wasn’t enough; they wanted ID. My son is older than 21, and sadly, I will never pass for that age again. I was clearly over 21, had already shown ID at check-in, and had a valid room key, but the guard made me go all the way back to my room to fetch it. No flexibility. No common sense. Just another hoop to jump through.

Later, I asked to speak with the general manager. She wasn’t around. A supervisor came out instead—polite, empathetic, and honest. She admitted she couldn’t change any of the policies and said, “If you really want to help, leave a bad review. Corporate doesn’t listen to us. But they do pay attention to bad reviews.”

That stuck with me. A front-line employee encouraged a customer to publicly criticize her own company, not out of spite, but out of desperation. Her experience in the five years she worked there taught her that the people at the top wouldn’t listen otherwise. It was also obvious they hadn’t stayed at their own hotel recently as guests, and found out for themselves, first-hand, how unfriendly and tone-deaf some of their policies really were.

And it’s not just hotels. My experience with a new healthcare provider was equally underwhelming.

After moving to a new state, I tried to sign up for my healthcare provider’s new patient app. The process, I was told, would be simple and only take a few minutes. They gave me a number to call from home to get help.

It took almost an hour, and that number sent me through six or seven different people, each suggesting a different course of action. Nobody knew for sure what I needed to do. They were all guessing.

Eventually, the app just started working. I got lucky. But I couldn’t help thinking: how many other patients gave up?

I filled out the patient satisfaction survey they sent after it was all over. I praised the medical staff, but laid out the failure of the app rollout. I got an email reply saying, “We’re sorry our service didn’t meet your expectations” as if the problem was with me or my expectations.

Later, I also received an email from a person on their staff who acknowledged my review and gave me her name and number if there was anything more I would wish to share with them.

I truly appreciated the offer to talk, and I called. After 18 minutes of transfers and repeating my info, I finally got through. The woman confirmed what I suspected—it should’ve taken one person a few minutes to get me set up on their app, and my experience didn’t meet their expectations either.

Then I asked her if she had the authority to affect the policies, procedures, and training necessary to fix these issues. No. Her job was simply to pass feedback to executives.

Clearly, the executives in charge had not recently experienced the pain of being a new patient OR a front-line employee dealing with the headaches and hassles resulting from their failures.

The executives were shielded from the chaos they created. They believed the absence of complaints meant patient satisfaction, when in reality, the lack of complaints and feedback, based on my personal experience, probably had a lot more to do with the amount of hassle and time it took to get anyone involved in their quality process to listen. In my case, it took 18 minutes, and I still hung up frustrated because the person I waited to talk to still didn’t have the power to fix the obvious problems associated with their app signup process.

So let me challenge you. If you’re in charge of a company, a department, or even a team, don’t assume silence equals success. Don’t assume your policies make sense just because no one’s pushing back.

Here’s What to Do Instead

Step 1: Work some frontline shifts.

Answer the phones. Handle customer issues. Do the grunt work. Feel the impact of your decisions from the bottom up.

Step 2: Be your own customer.

Call your own help desk. Try your own app. Stay in your own hotel. Follow every step your customers do, without using your title to skip the line.

What you’ll learn might change the way you lead, educate staff, or select the caliber of people on your team.

Spreadsheets won’t tell you when people feel cheated. Reports won’t show you the moment someone gives up trying to offer their feedback. Employees who want to preserve their jobs might be inclined to tell you what you want to hear, exaggerate good news, or sugarcoat what can sometimes be some ugly truths.

If you really want to know what’s broken in your business, start experiencing it like your customers and front-line employees do.