The Customer-Driven Culture: A Microsoft Story

How This Book Came to Be: A Note from Travis

There’s a reason this book is titled “a Microsoft Story.” Microsoft has played an essential role in the most critical and transformational moments of my personal life and professional career.

I was growing up in a small, dusty farming town in the center of California when computers started showing up as something you could buy for your home. During this time, no one in my family knew how to turn one on. Including me. It was my older brother, Ryan, who was the computer genius of the family.

One summer, he saved up enough money to buy a Compaq Presario 400 Series all-in-one computer. It came preloaded with Microsoft’s Disk Operating System (DOS) and Microsoft Windows 3.1.

I was 13, and when he loaded Wolfenstein 3D and let me hunt Nazis in an underground dungeon maze, I completely lost my mind. It was the coolest thing I’d ever laid my hands on. I was hooked.

This was before the internet, so there was no “Googling it” when you had a computer problem. There was no one on YouTube to show you how to fix a corrupt config.sys. You did a lot of trial and error in those days, and only the persistent would survive.

Thankfully, I persisted. I struggled, shouted, and yes, probably even cried, but I finally figured out how to use the blasted thing.

Microsoft was there for the entire experience; from the Command Prompt, to the Program Manager, to Solitaire and Minesweeper.

I can still remember, way back in 1995, when I clicked the “Start button” for the first time.

I took advantage of the power of the Microsoft Encarta CD-ROM when completing school assignments, and I remember the awe I felt when Internet Explorer finally connected me to the internet.

In college, I used Microsoft Visual Studio and .NET to build my very first applications. Sure, they were simple calculators and command-line scripts that would make ASCII art using special characters, but the feeling of commanding the computer to do something I designed was profound and intoxicating.

When I finished my undergrad, I used Microsoft Word to draft up a résumé and was hired to work on internal ASP.NET web applications at a children’s hospital.

Later, when I discovered the field of Human–Computer Interaction, I wanted to pivot my career in a completely new direction. However, there were no schools within a 200-mile radius where I could pursue this field in my graduate studies.

With the help of the internet, Microsoft Office, and a university tool built on Microsoft technology, I was able to enroll in remote learning and achieve a graduate degree from DePaul University in Chicago. I was able to access a world of education without having to uproot my family or move anywhere.

For four years, my brother and I hosted the Windows Developer Show, a podcast in which we would interview Microsoft developers and enthusiasts from all over the world. It was an incredible community to be a part of and truly inspiring to hear stories of how fans of Microsoft tools and platforms were driving the future of computing. Microsoft Skype played a fundamental role in allowing us to connect with our funny, brilliant, and inspiring guests so that we could share their stories.

In 2013, I was eventually invited by Microsoft to interview for a UX Designer position with the Developer Division (DevDiv).

DevDiv is responsible for most of the developer tooling Microsoft ships from the company. Chances are, some of the apps you use today were built by a developer using Visual Studio or Visual Studio Code. In fact, if you’re using any Microsoft product now, there’s a very good chance it was created using a tool built in DevDiv.

I’ll never forget the day of my interview. A Microsoft Connector bus came to pick me up and whisk me to campus. These Connectors were everywhere.

I asked the driver, “Are these Microsoft cars and busses for employees?”

“Oh yes,” he replied over his shoulder, “We’ll take you anywhere you need to go, on campus and even into Seattle. Free of charge. The buses even have WiFi.”

I couldn’t believe it. I had entered some sort of metropolis of the future.

When he pulled up to the corner of Microsoft Building 40, I stepped off the bus and took stock of my surroundings.

There was a bustle of important and smart people rushing everywhere. The Microsoft campus was the biggest thing I’d ever seen. California State University, Fresno, where I had studied for my undergrad, was a third of the size. Microsoft’s campus could’ve easily housed 20 of the hospitals I was currently working at, and probably had room for more. It was awe inspiring.

I immediately felt out of my depth.

When you’re scheduled for an “interview loop” at Microsoft, it’s a whirlwind day full of introductions, questions, and in my case, a design portfolio review and a “design challenge.”

I met so many people that day. Everyone was gracious and kind, but they pushed me and challenged me at the same time. They were so cool and interesting and, about two hours in, I was desperate to work with all of them.

Out of the dizzying array of people I met that day, there’s one person who stood out because he was simply impossible to forget.

He was a gray-bearded, tall guy who never stopped smiling.

Seriously.

He was smiling during my portfolio review, smiling throughout my design challenge, and smiling during my one-on-one interview with him. I remember thinking to myself, “Either this guy is smiling because he likes me or he’s trying not to laugh because I’m a disaster.”

When I finally met with him, we talked about literally everything. In a span of 2 minutes, he hit me with 10 books I’d never heard of, citing authors, quotes, and specific chapters that I “absolutely needed to stop everything and read!” because I would “drool all over it.” I desperately tried to capture everything he was telling me. I kept thinking to myself, “I may never see this guy again, so I better remember everything he’s telling me right now.”

He had so much energy it was impossible not to feed off it. He was physical; if you said something that made him laugh, he’d slap you on the back. At one point, we were walking down the hallway, and he gave me a spontaneous high five. He made you feel special; but most important that day, he made me feel like I was exactly where I was supposed to be.

I liked him immediately.

Little did I know that day that the venerable Dr. Monty Hammontree would eventually become my boss, mentor, creative partner, and dear friend.

Monty has an affable southern charm; he’s gentle but persistent and purpose driven. He grew up playing basketball, so he’s competitive and will push you for excellence, but never in a way that makes you feel like you’re not valued. If you find yourself in a debate with Monty, he’ll go round for round with you, never once pausing for water or a towel.

There’s no job too big or too small for Monty. He can be planning a wide-sweeping event for our entire division and still pause to vacuum our team room.

He’s the “vision master.” He’s the guide that pulls you aside, points to the horizon, and says, “No one’s looking over here, but this is where the gold is buried.”

And he’s right. A lot.

I know this because he’s proven me wrong. A lot.

I’ve tried to describe my relationship with Monty by telling people, “He’s the Doc Brown to my Marty McFly.” Those of you who are familiar with the film Back to the Future might get the reference.

Emmet “Doc” Brown (played by Christopher Lloyd) is an enigmatic inventor who strikes brilliance by creating a time machine out of a DeLorean. Marty McFly (Michael J. Fox) tags along and gets to have thrilling adventures.

That’s what’s happening with this book.

I’ll be taking the helm as narrator to share the lessons we’ve learned in how to move an organization toward customer obsession. Monty is the enigmatic inventor who saw all these lessons before I did. Without him, this amazing adventure would never have happened.

In the book Multipliers: How the Best Leaders Make Everyone Smarter, author Liz Wiseman talks about geniuses who make everyone around them smarter. That description fits Monty completely.

He has a way of seeing what you’re capable of well before you do. He labels it and shows you how to harness and grow it. He pushes you hard, but only because he believes in your potential to achieve more.

Numerous times, I’d come into his office freaking out and in complete imposter syndrome–meltdown mode. I didn’t come from some Ivy League school. I hadn’t worked with the best in our industry. I didn’t even have a PhD. I was a nobody from a town that no one had ever heard of. In a big company, where there’s a specialist for just about everything, this can be terrifying. It’s scary trying to find your unique value in a company of more than 100,000 employees. Working at Microsoft was a dream come true, and I was convinced I was going to blow it.

Thankfully, Monty knew exactly what my contribution would be.

He showed me that I could easily ebb and flow between technical, design, human interaction, and user research conversations. He demonstrated how well I understood the company, because I had been an obsessed fan all these years. He pointed to the work I was doing and said that, in the nearly 40 years of his career, it was “the best he’d ever seen.”

He described how I was able to help teams understand abstract ideas by boiling them down to their essential parts. He pointed to all the people I had mentored and influenced over the years.

He said, “You’re a generalist. That’s your superpower. You help teams connect with their customers and each other. That’s why you’re here.”

This was coming from someone who was on the ground floor of some of the most innovative work in user research. Monty is a partner-level director of research at Microsoft. This is a title reserved for only a select few user experience researchers in the history of the company. If someone of that caliber believed in me, there just wasn’t any room for me to doubt myself.

Monty leaned into what I was passionate about. I had spent nearly a decade in my previous job as part of an organizational change movement to increase the satisfaction of our patients. My day job was in database administration and software development; but on the side, I would coach and mentor teams, teaching them strategies to better connect with one another and their patients.

I didn’t think any of this was important. Company culture, team building, and organizational behavior had always been a side passion of mine, but I didn’t see how that was going to be useful at a software company. However, Monty saw the bigger picture. With a new CEO, there was a strong desire to reclaim our purpose and be a company that obsessed over its customers. Monty knew how to exercise my skills just when the company needed them most.

As we worked to help transform the culture of DevDiv, Monty was patiently and persistently mentoring me through my own transformation.

Time and again, he showed me how to direct my energy toward these goals:

• Use a common language of learning.

• Build bridges and tear down walls with humility and a sincere desire to give my expertise away.

• Shape, mentor, and mold new leaders that embody the culture that you want to build.

• Be pragmatic and meet people where they are instead of forcing them where you want them to be.

• Help teams make the data they are collecting relatable to inspire others to action.

• Identify the vital behaviors necessary for culture change and how to measure them so that they can be repeated.

These lessons—what we call culture hacks—became the culture change journey on which we took our workgroup, our division, and eventually many other groups from all corners of Microsoft. Sharing these hacks is the purpose of this book.

There are so many other talented people at Microsoft who are working hard to help us all achieve a little bit more. They inspire me, and I am in awe of the people I get the opportunity to work with. Their work is a big part of this book, too. There are just too many people to mention them all here, but hopefully I’ve told them how much they’ve meant to me over the years.

I’m still that kid from that small, dusty farming town, but I’m humbled and eternally grateful to be the one who gets to share these culture hacks with you. I sincerely hope you find as much meaning in them as I have.

Figure I-1. Travis Lowdermilk and Dr. Monty Hammontree—yes, that is a wig (photo credit: Hannah Lewbel)