How do you make someone feel something in a fully digital experience?
It’s a question that’s been on my mind a lot lately—especially as we build increasingly automated, scalable customer programs. And if we’re honest, a lot of what we call “personalization” today is… well, pretty impersonal.
But after a short break from podcasting, I came back with a new perspective. One inspired by a book called Unreasonable Hospitality – and by the little, unexpected moments that make customers say: “Wow, they really see me.”
In this article, I’m sharing why hospitality isn’t just for restaurants—and how you can build systems that help your team spot and act on those magical moments. Let’s get into it.
1. What Is Unreasonable Hospitality?
Will Guidara’s Unreasonable Hospitality chronicles how Eleven Madison Park became the world’s best restaurant, not just through food, but through moments. The hot dog story is now legendary: a simple street dog served on fine china because a guest mentioned they missed out on trying one.
What made it unforgettable? Listening. Acting. Caring. And that’s where digital CX can learn a thing or two.
2. Why These Moments Matter in Digital CX
Here’s the thing: most digital CX programs focus on process and scale. And that’s good—we need systems. But emotional loyalty? That’s built in the moments outside of the expected.
When we show up with a surprise gift, a thoughtful note, or a small gesture, it creates connection. Not because it’s flashy, but because it’s human.
3. Tools That Can Help You Scale the Unexpected
Here’s where it gets exciting.
You can use tools like Gong to “listen” to customer conversations—automatically scanning for key phrases or life events. Combine that with automation platforms like Zapier or Make.com, and you can surface those signals to your team, fast.
Want to send a handwritten note? Services like Handwrytten can do that for you, straight from your CS platform.
4. What It Takes: Budget + Autonomy + Empathy
None of this works without empowering your team.
Set aside a small monthly budget—$200 goes a long way when you’re sending gifts, flowers, or notes. More importantly, trust your CSMs or support reps to act. No approvals needed. Just intent.
It’s not about the object—it’s about the message: “We’re paying attention. We care.”
5. Making Hospitality a Digital Strategy
This isn’t fluff. It’s a differentiator.
Unreasonable hospitality at scale requires a blend of systems thinking, budget ownership, and cultural mindset. But when done well, it creates customers who feel like partners—not just users.
That’s how you stand out in today’s digital world.
Conclusion
Hospitality doesn’t belong to hotels or restaurants. It belongs to anyone who wants to serve better.
As digital leaders, we have the tools—and the responsibility—to bring more human connection into the programs we build.
So… what’s your “hot dog moment”?
🎧 For more stories and strategies like this, tune into the Digital Customer Success podcast. And let me know how you’ve scaled hospitality in your digital programs.