The One Question Great Leaders Never Stop Asking

Discover how a single question sparked a 4-billion-dollar acquisition and why the best leaders never stop asking it.

Today’s guest post is by Joseph A. Michelli, Ph.D., author of All Business is Personal. 

What if one question could reshape your industry?

In the early 2000s, Tom Lee, a Harvard and Stanford-trained primary care physician, was frustrated by outdated, impersonal, and inefficient primary care delivery. Instead of accepting things as they were, he kept asking a deceptively simple question: “Why?”

Why do patients have to call to make an appointment?

Why can’t patients regularly get same-day or next-day appointments?

Why do patients wait in a waiting room and an exam room?

Why are doctor’s offices so bland?

Why do appointments feel rushed?

Why do doctors feel burned out?

And why does the system seem broken?

That persistent curiosity led Dr. Lee to build One Medical, a disruptive healthcare brand that blends hospitality, technology, and personalized care. The company grew from one office in San Francisco to over 200 across the U.S., ultimately attracting Amazon’s attention and culminating in a $4 billion purchase. All this happened because one leader kept asking why and refused to accept “we’ve always done it that way” as an answer.

Great leaders never stop asking why. Their insatiable curiosity is at the heart of every innovation, cultural shift, and lasting business transformation. I’ve studied and written about the importance of leadership and value creation in thirteen business books about companies like The Ritz-Carlton, Starbucks, and Mercedes-Benz.

In my new book, All Business is Personal, I explore how transformational leaders consistently elevate personal experiences for customers and employees. At One Medical, this starts with understanding everyday challenges faced by team members and patients and then designing processes and technologies that resolve those pain points. Visionary leaders challenge the status quo as they seek to make both iterative improvements and industry-changing, customer-centric breakthroughs.

Here are three takeaways from Dr. Tom Lee’s story and the broader story told in All Business is Personal—lessons any leader can apply immediately:

Ask Why—But Ask With Purpose

Leaders like Tom Lee ask why as a springboard to improved human experiences. The question opens the door to uncovering root causes and unleashing creativity and positive disruption. Whether you’re in healthcare, retail, finance, or manufacturing, build the habit of asking:

Why do we do it this way?

Why does our process create friction for customers or employees?

Why are past attempts to address this issue not creating a lasting solution?

Asking with curiosity—not criticism—builds trust and inspires innovation. The best ideas often come from frontline team members, and our job as leaders is to create an environment where team members can and will offer ideas that lead to better human experiences.

Design with Empathy for Efficiency

Tom Lee’s redesign of the primary care experience didn’t begin with technology or cost-saving goals. It began with empathy. He adopted the perspective of patients and healthcare providers. In essence, he asked,

What would make a primary care visit more humane, respectful, and accessible?

With a foundation in empathy, many of One Medical’s breakthroughs have been technological (e.g., a proprietary medical record, a highly used patient app).  These technologies allow patients to self-serve efficiently while offering team members more time to engage patients personally.

From a leadership standpoint, empathetic design leverages customer and employee feedback to develop customer-centric improvements in people, products, processes, and technology.

Lead Change by Modeling Curiosity

Culture flows from the top. If your team sees you asking questions, listening to feedback, and adapting based on what you learn, they’ll act accordingly. If you provide all the answers, interrupt, and seek quick fixes – so will they.

Whether you lead five people or five thousand, your lasting leadership impact will likely be shaped more by the questions you bravely ask instead of the answers you quickly give.

The One Medical story, one I’ve been blessed to be a part of as a customer experience and leadership consultant, shows that balancing cutting-edge technology with human service creates personal and loyalty-building relationships with team members and customers. That successful and innovative balance starts with a single question:

Why?

If you ask “why” often and listen well, your customers and employees will respond with loyalty, trust, and four billion reasons to keep asking.

Joseph A. Michelli, Ph.D., CSP, is an international speaker and New York Times #1 bestselling author of books about companies like Starbucks, Zappos, Mercedes-Benz, and his latest about Amazon One Medical – All Business is Personal: Human-Centered and Technology-Powered Customer Experiences.

Did you enjoy this post? If so, I highly encourage you to take about 30 seconds to become a regular subscriber to this blog. It’s free, fun, practical, and only a few emails a week (I promise!). SIGN UP HERE to get the thoughtLEADERS blog conveniently delivered right to your inbox!