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did not yet have a commercially viable cloud platform.

      All of this spelled trouble for Microsoft. Even before the Great Recession of 2008, our stock had begun a downward slide. In a long-planned move, Bill Gates left the company that year to focus on the Bill & Melinda Gates Foundation. But others were leaving, too. Among them, Kevin Johnson, president of the Windows and online services business, announced he would leave to become CEO of Juniper Networks. In their letter to shareholders that year, Bill and Steve Ballmer noted that Ray Ozzie, creator of Lotus Notes, had been named the company’s new Chief Software Architect (Bill’s old title), reflecting the fact that a new generation of leaders was stepping up in areas like online advertising and search.

      There was no mention of the cloud in that year’s shareholder letter, but, to his credit, Steve had a game plan and a wider view of the playing field. Always a bold, courageous, and famously enthusiastic leader, Steve called me one day to say he had an idea. He wanted me to become head of engineering for the online search and advertising business that would later be relaunched as Bing, one of Microsoft’s first businesses born in the cloud.

      For context, search engines generate revenue through a form of advertising known as an auction. Advertisers bid on search keywords that match their product or service; the winning bid gets an opportunity to display a relevant advertisement on the search results page. Search for a car and a car dealership has likely paid to be displayed prominently on your results page. Delivering that purchase experience both from the consumer and the advertiser perspective is computationally expensive and sophisticated. And while Microsoft was struggling with low market share in search, Steve had invested in it because it would require the company to compete in a sector beyond Windows and Office and build great technology—which he saw as the future of our industry. There was tremendous pressure for Microsoft to answer Amazon’s growing cloud business. This was the business he was inviting me to join.

      “You should think about it, though,” Steve added. “This might be your last job at Microsoft, because if you fail there is no parachute. You may just crash with it.” I wondered at the time whether he meant it as a grim bit of humor or as a perfectly straightforward warning. I’m still not quite sure which it was.

      Despite the warning, the job sounded intriguing. I was running an emerging new business within Microsoft Dynamics. I had taken over from Doug Burgum who later would become the governor of North Dakota. Doug was an inspirational leader who mentored me to become a more complete leader. He thought about business and work not in isolation but as part of a broader societal fabric and a core part of one’s life. Some of the lessons I learned from Doug are today an important part of who I am as a leader. Leading the Dynamics team was a dream job. For the first time, I was getting the chance to run a business end to end. I had spent nearly five years preparing for this job. I had all the relationships, inside and outside Microsoft, to drive the Dynamics business forward. But Steve’s offer was essentially pushing me out of my comfort zone. I’d never worked in a consumer-facing business and had not really tracked Microsoft’s search engine efforts or our early attempts to build cloud infrastructure. So one night, after a long day at work, I decided to drive over to Building 88, which housed the Internet search engineering team. I wanted to walk the hallways and see who these people were. How else could I empathize with the team I was being asked to lead? It was about 9 p.m., but the parking lot was packed. I’d expected to see a few stragglers finishing up their day but, no, the whole team was there working at their desks and eating take-out food. I didn’t really talk to anyone. But what I observed caused me to wonder: What gets people to work like this? Something important must be happening in Building 88.

      Seeing the team that night, their commitment and dedication, clinched it for me. I told Steve, “Okay, I’m in.” What color was my parachute? I didn’t have one.

      I was entering a new world, and the move proved to be fortuitous. Little did I know it would be my proving ground for future leadership and the future of the company.

      Very quickly I realized we would need four essential skills to build an online, cloud-based business that would be accessed primarily from mobile phones rather than desktop computers.

      First, I thought I knew a lot about distributed computing systems, but suddenly I realized I had to completely relearn these systems because of the cloud. A distributed system, simply put, is how software communicates and coordinates across networked computers. Imagine hundreds of thousands of people typing in search queries at the same time. If those queries landed in just one server somewhere in a room on the West Coast, it would break that server. But now imagine those queries being distributed evenly across a network of servers. The vast array of computing power would enable delivery of instant, relevant results to the consumer. And, if there’s more traffic, just add more servers. This elasticity is a core attribute of cloud computing architecture.

      Second, we had to become great at consumer product design. We knew we needed great technology, but we also understood we needed a great experience, one you want to engage with time and again. Traditional software design mapped out what developers thought a product should look like in a year’s time, when it would finally go to market. Modern software design involves online products updated through continuous experimentation. Designers offer Web pages in “flights,” so an old version of Bing is delivered to some searchers while an untested new version reaches others. User scorecards determine which is the most effective. Sometimes, seemingly tiny differences can mean a lot. Something as simple as the color or size of a type font may profoundly impact the willingness of consumers to engage, triggering behavioral variations that may be worth tens of millions in revenue. Now Microsoft had to master this new approach to product design.

      Third, we had to be great at understanding and building two-sided markets—the economics of a new online business. On one side are the consumers who go online for search results, and on the other side are the advertisers who want their businesses to be found. Both are needed to succeed. This creates the auction effect I was describing earlier. Both sides of the business are equally important, and designing the experience for both sides is crucial. Attracting more and more searchers obviously makes it easier to attract more and more advertisers. And showing the right advertisements is crucial to delivering relevant results. So, “bootstrapping” the online auction and improving search results’ relevance would prove to be a vital challenge.

      Finally, we needed to be great at applied machine learning (ML). ML is a very rich form of data analytics that is foundational to artificial intelligence. We needed a sophisticated understanding of how to do two things at once—discern the intent of someone searching the Web and then match that intent with accurate knowledge gained from crawling the Web, ingesting and understanding information.

      Ultimately, Bing would prove to be a great training ground for building the hyper-scale, cloud-first services that today permeate Microsoft. We weren’t just building Bing, we were building the foundational technologies that would fuel Microsoft’s future. Building Bing taught us about scale, experimentation-led design, applied ML, and auction-based pricing. These skills are not only mission critical at our company, but highly sought after throughout today’s technology universe.

      But we started very much behind in search; we had yet to launch a product that could compete with Google. So I hit the road, meeting with executives from Facebook, Amazon, Yahoo, and Apple to evangelize our emerging search engine. I wanted to make deals, but I also wanted to learn more about how they engineered their products to stay fresh. I found that the key was agility, agility, agility. We needed to develop speed, nimbleness, and athleticism to get the consumer experience right, not just once but daily. We needed to set and repeatedly meet short-term goals, shipping code at a more modern, fast-paced cadence.

      To accomplish this, we needed to periodically gather all of the decision makers in a war-room setting. In September 2008 I called together the search engineers for the first of these meetings, which we casually called Search Checkpoint #1. (Perhaps we should have been more creative with the name, because it has stuck and now we’re at a checkpoint in the many hundreds.) We had decided to launch Bing in June 2009—a new search engine and a new brand. I learned a lot about creating urgency and mobilizing leaders with different skills and backgrounds toward one common goal in what was a new area for Microsoft. I realized that in a successful

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