Mistakes Don't Kill Loyalty — Broken Promises Do
Opinions expressed by Entrepreneur contributors are their own.
Loyalty earns you the opportunity to make a second mistake. I learned this working at USAA, a financial services organization famous for its member loyalty. During one particularly isolated system outage, I called a member who had banked with USAA for over 50 years to apologize. He said, "Don't worry about it," he said, "you guys are normally so on top of things, so this must be a tough one to crack. I trust you."
That experience stuck with me — not because it made loyalty sound transactional, but because it revealed something deeper: true loyalty isn't about perfection, it's about trust. And trust is built over time, mistake by mistake. It's a lesson I've carried with me into business. After 20 years in leadership roles, and now as CEO of Boardroom, a national upscale men's grooming salon, I believe loyalty hasn't vanished — but it has evolved. Today's clients, employees, and partners are loyal because you earn that trust over and over again. Here's how you should approach that challenge.
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Experience, not proximity
There was a time when your dry cleaner, your bank — even your barber — earned your loyalty simply by being nearby. Those days are gone.
Clients today have more options than ever. What keeps them coming back is a combination of convenience, the experience you provide, and the relationships you build. At Boardroom, we realized that to create something lasting, we had to be more than just "good." We had to be consistently better than expected.
That means obsessing over the details — from the hi's to the bye's. We want every visit to feel like more than a service — it has to feel like an experience.
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People are still the heart of loyalty
As a society, we've embraced technology to streamline things. This includes the client journey — but no app can replicate what happens when someone feels genuinely seen. Your people should create those moments. For example, a stylist asks a client about last week's job interview. A front desk team member notices a regular seems time-pressed and offers a streamlined service to get them on their way. A warm smile and greeting by name when a client walks in.
Loyalty inside the business is just as vital as loyalty from the outside. When your team is invested, your clients can feel it. One of our earliest team members, who helped open our very first salon 20 years ago, is still with the company today. Her loyalty isn't just a testament to her commitment, it's a reflection of how she's been treated, empowered, and valued through every season of our growth. And her consistency has earned the loyalty of hundreds of clients over two decades. That's the compound interest of trust.
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Your promise doesn't change
I've had to make bold moves in my business history, as many have — closing our office and going fully remote, expanding through M&A and franchising, and introducing new technologies. Change is part of growth.
But through those shifts, it's important that your promise doesn't change. For us, it's always been to help men relax, look great, and feel confident by delivering a better experience than expected and treating them like they matter. That mission has stayed rock solid, even as the methods evolve.
And it's working. Our existing client retention has improved by 6 percent over the past year — and we're still improving.
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Authenticity is the future
We're entering an era where technology can simulate connection. Companies are spending billions to deepen this synthetic familiarity—but in doing so, they're commoditizing trust. I get automated emails every day that inject my name, my title, my professional history — even my love of the Red Sox — and they always feel just a little off. The leaders and companies who win long-term will be the ones who invest in authentic relationships. The ones who earn their reputation through consistency, not cleverness. Through presence, not programming.
Loyalty isn't a lifetime pass, it's a daily effort. It's built when people see you at your best and worst — and you show up for them either way. I've been lucky to work with clients, colleagues, and teammates who've given me that opportunity to make a second mistake. My goal is to make each one count, because when loyalty is earned, it endures.
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