067. MYR-CDG: Product Meets Sales
The entire room turned to look at me like I was the last human in "Invasion of the Body Snatchers".
Microsoft was often viewed as a Borg-like structure though we’ve already seen when it came to product development it was decidedly of two cultures. The huge and growing global sales force so dominated by SteveB (now CEO) represented a third, one completely defined by the unique combination of massive global scale and local empowerment and respect for culture. What happens when a Redmond-based software engineer-turned product group executive meets this culture head-on? What about when that happens in front of his new boss who previously ran the field and created the process we’re about to see unfold?
This is a story of culture. It is also a story of growing and maturing as an exec. Most of all it is a story of how a product leader is not really complete until they’ve lived and breathed the efforts of the sales people that connect with customers and bring in the money. Below is an early experience. A few years later I would pack up and live in China to experience firsthand on a daily basis what it was like to sell every day.
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Back to 066. Killing a Killer Feature (In Outlook, Again)
In the classic book Flow: The Psychology of Optimal Experience, Mihaly Csikszentmihalyi demonstrates that a genuinely satisfying experience takes place in a state of consciousness called flow. During flow, people typically experience deep enjoyment, creativity, and a total involvement with life. While the book uses many examples, the concept of getting in a groove resonated with me. Flow is how programmers spend hours writing code and how our best customers spend hours creating satisfying documents with Office.

Reading Flow helped me, but my job was changing. . .a lot. The demands to be present in the newly added building 34 executive suite overwhelmed me at times. The pressure to spend so much time ruminating with other executives ran counter to what I came to believe and what I experienced. It didn’t used to be like that. I know because I used to see the execs I worked for most every day, casually.
Flow was how I felt writing a vision or the interactions I had as I walked the halls. This was especially important at Microsoft where everyone had a door. The criticism of private offices is that people get shut out of collaboration and spontaneous discussions (in favor of concentration and quiet focused work, apparently). I never believed that to be the case, because we had a culture of door open/door closed that implied a willingness to chat spontaneously or a need to focus. Since my first days at work, the richness of the hallway discussion and drive-by discussions were the most useful and memorable.
The idea of connecting spontaneously and learning what was on the mind of a member of the team was something I viewed as my job—so much more than sitting in a conference room with other executives or reading slides presented by managers but prepared by people not even in the room. Making eye contact, not in a hurry, discussing someone’s work, and seeing if I could put if either into context, or simply offer perspective on something going on in a bigger picture—that was flow for me. Everyone was always wrestling with something—bugs, recruiting, implementation choices, and more—and while I didn’t want to walk around fixing things, I could support, learn, and connect. Most importantly, this was a way to connect with less senior members of the team 1:1. Even today, I can recount some of my favorite moments and best connections coming from people I was able to learn from by walking the halls, a phrase made famous (at least in the tech world) by Intel’s Andy Grove.
Doing so was not the norm for many execs, especially outside Apps or the product groups. The vast majority kept to a Microsoft exec workflow of a reserved conference room across from their office and a steady stream of meetings all day. Even 1:1s were often held in bigger conference rooms.
The 8 a.m. meetings, the meetings to prep for meetings, the emails written by staff to communicate the meetings, the rescheduling of the same, were all starting to pile up. I felt I was becoming detached from the team—I was losing flow. I was uncertain of whether I was a poor fit for the role or if my role was defined wrong. I struggled trying to understand what changed in the landscape that required such a change in how to manage. We weren’t facing new problems or new concerns—there were no new competitors or competing technologies. We had ideas to grow to new areas and were executing, and the enterprise sales process was yielding absurdly good numbers. What was I missing? Or, how could I convince people that managing 2,500 people was an investment in time that might be different from how a huge subsidiary GM or marketing VP ran things? Others in similar positions felt differently. They seemed to gravitate to this new Microsoft culture. Perhaps I was wrong or underestimated what was needed to operate at scale and that was the driving force behind this perceived shift.
The field’s annual Mid-Year Reviews (MYR), the process JeffR pioneered, were the most coveted meetings for field teams to attend. If there was a culture-defining element to the growing and incredibly successful enterprise field it was MYR, and it could not be more different than anything we did in the Redmond BGs (Business Groups, as we were called to imply we were separate businesses rather than mere product teams). BG was the new term for the teams in Redmond and everyone loved to say it as a differentiator to the field. Everything seemed to come down to the BG versus the field. It was as if Microsoft was a BG brain and a field brain in a constant struggle.
To say MYR was a production would be like calling the Olympics “some people playing sports.” Over the course of three weeks or more in January, the company’s collective leadership focused entirely on syncing up at various locations around the world and presenting mid–fiscal year results. Each year the process became more elaborate, took longer, involved more people, and became more all-consuming with ever-increasing import. Every country, though some were presented in regions, marched through a standardized slide deck slicing and dicing sales budgets and forecasts, finding holes, ferreting opportunities, and sharing best practices. These meetings were tense, terrifying, and a test of thinking on your feet under the harshest (of business) conditions.