The Retreat Observation That Put Patty Stonesifer on Microsoft Leadership’s Radar

Within a month, she was running Microsoft Canada.

Patty Stonesifer in 2001.
Patty Stonesifer in 2001 Photo illustration by Slate. Photo by Yves Herman/Reuters.

This week, Slate published a special five-episode mini-season of the Working podcast about “second actors”—people who have made a dramatic career pivot at some point in their work lives. Patty Stonesifer talked with June Thomas about her career path from senior vice president at Microsoft, to running the Bill & Melinda Gates Foundation, to serving as president and CEO of Martha’s Table, a small D.C. nonprofit.

Their conversation, which is excerpted below, has been lightly edited for clarity.

Listen to the whole conversation below or get the show via Apple Podcasts, Overcast, Spotify, Stitcher, or Google Play.

June Thomas: You’ve had many more than two acts. Could you outline the various stages of your career?

Patty Stonesifer: I zigzagged quite a bit in my career, or multiple careers. I started out dropping out of college and needed to find work that would allow me to put my husband, who I met in college, through school. I became a technical writer at that time. The technical writing was always about this new computing that was going on, and it turned out that I had a real flair for it, and I moved from technical writing to training right away and spent the next 20 years riding the line between those who are creating new technologies and those who are consuming new technologies. I spent almost a decade at Microsoft. That was the last stop on my 20-year career in technology.

At the end of that time, I was 40, I had had more success than I ever thought, and I knew it was time to rethink what I wanted to do next. At my going-away party, Bill Gates mentioned that he wanted to talk about this philanthropy that he and Melinda were beginning to expand. They had been doing it with their dad out of his house and their kitchen table, and so a few months later, I started the Gates Library Foundation. A year after that, we created the Bill & Melinda Gates Foundation, with Bill’s dad and myself partnered as the day-to-day leadership of this wonderful new philanthropic endeavor. I did that for another decade plus, and then as Bill Gates exited Microsoft, I exited the foundation, which I had loved and built. It was a logical time for me to transition, and I came to the nonprofit world, which is where I am today finishing my third career, which I’ll retire from later this year.

When you first went to Microsoft, you were working as the editor in chief of a computer book publisher in Indianapolis. Do you ever think how different your life had been if you hadn’t applied for or hadn’t gotten that job at Microsoft?

As of yet, there have been very few jobs I’ve ever applied for. They were on a hunt for grown-ups, and at 30 years old, I was considered a grown-up in the technology field.

Microsoft had a book publishing one called Microsoft Press, and so they called and asked whether I would consider joining them. I’d been writing books and editing books about Microsoft products. I had two young children, and Seattle looked fantastic. (They must have caught me on a wintry day in Indianapolis.) It seemed like it would be a place to continue my belief that this new microcomputer technology could expand access to technology for so many people. It was also a company that was willing to take risks and try new things—it really fit the entrepreneurial spirit that I’d developed at this small book publisher. It seems like a big leap, but it looked to me like a great family choice and a great career choice. I had no idea that Microsoft would end up being the No. 1 player in all of these categories. I don’t think that any of us really understood how rapidly that would happen at that point.

What kind of work did you do at Microsoft?

I did so many different jobs, and that was one reason that it was such a wonderful experience and that I extended it for a whole decade. I came in to run Microsoft Press, so I did pretty much the job I’d been doing in Indianapolis: identifying opportunities for books, finding writers, reviewing manuscripts, and working with the publishing sector to make sure those books got out and got sold. It was very typical of a computer book publisher, which is the organization I’d left in Indianapolis. But very shortly after I got there, within the first year, I went to a Microsoft leadership retreat, where they would pick “young leaders” from across the company and take them on a retreat with the top honchos, which were, of course, at that moment all men and all very technical.

At that retreat they would take on three or four big questions that were similar to three or four big questions the executives themselves were grappling with. They identified that they should grab me out of book publishing and start moving me around the company. Within a few weeks, I was in Microsoft International Division, and within a month, I was running Microsoft Canada and moved to Canada to run the subsidiary there. I learned about all aspects of Microsoft, having been very focused on the computer book business, learning all of it very rapidly as well as all the customers and just continued from there. My very last job was as the senior vice president of what was then called the Interactive Media Division, and the shorthand I tell people is that if you had a lot of fun using a Microsoft product, that was one of mine.

It was the internet products, the mouse and the keyboard and the joystick, and it was also Publisher and Expedia and other products that were designed to be used by the consumer to further enhance their lives—not necessarily their business, but their lives. I got to be there at the launch of Encarta, at the beginning of a whole range of new businesses, some of which made it and some of which are in very different forms. The one that I’m most excited about was Slate, because not only was that part of the portfolio of products that was in my division, but that’s where I met my husband, Mike Kinsley, who came to Microsoft with this idea that political and cultural commentary could be taken to a new level online. I met him in his interview loop, and the rest is our personal history.

Do you remember what it was that you said at that retreat that got everyone’s attention?

I do. One of the scenarios was: There’s a great recession and suddenly people are spending less, and our retailers don’t have the cash to buy more software and are in an unbelievable pinch. What do we do in this recession? Most of the people said, we hunker down, we cut costs, we do X and Y. We had a good cash balance, and my belief was that if you look at history, recessions don’t last forever. We should extend credit to the retailers. We should make sure to push forward with the developments that we were on. Basically, I said we could hold our breath longer than anyone else. Holding your breath during a period of want, of recession, and doing the work you were focused on doing—at the end of the recession, you could come out much, much stronger. Just the idea that I was both a risk-taker but had a plan behind it got a lot of attention that I guess it was unusual. But coming from a more entrepreneurial background, it was logical to me that you would say, “We’re already a risk business, you take this risk.”

That’s a useful reminder never to get too hungover at a retreat, to bring your A-game.

Well, I was going to stand out anyway because there were only two women at the whole retreat. You go into that knowing they’re going to notice, but it’s a matter of what they notice.

I’m very curious what kind of hours you were working by the end of your first career as it were at Microsoft? We tend to think of tech companies being places that demand very long hours, obviously, being in the executive team is also incredibly demanding. As you said, you had two kids at this time. How was the workload? And I’m curious how that has evolved over the course of your careers.

I’ve always been somebody with a very strong inclination to work. I love work, I love being productive, I love making a contribution. I also love my family, and at that time, there was a lot of discussion about life balance, and there were these pictures of this wonderful array of life balance things. I always said I didn’t have a wheel, I had a teeter totter, I had family and work. So I concentrated heavily on both of those, family and work, and it was a very rich experience. I didn’t develop much in my other areas, I wasn’t out pursuing music or theater or spiritual life or many of the other things I neglected during that period, but I had a very rich work life and a very rich family life.

Thankfully, I was not carrying an email device on my hip at that time, that wasn’t yet a factor. We all logged in at night and did a lot of work after the kids were in bed, but I worked a fairly reasonable schedule. I had to travel a bit because, of course, I was selling products as well as building products, and I had to represent the work around the country and around the world. But for the most part, I would work a good nine- or 10-hour day, go home, have the evening with the family, and then log back on to the clunky computers of the day in the evening. Today, I think, young family leaders have it more difficult, and that the presumption of being always on is very real. There really was a bloc in the evening where I knew things might be piling up, but I could get to them later and they weren’t beeping or chirping on my hip.

OK, so it was time to leave Microsoft. As you mentioned earlier, you were approached by Bill Gates, but didn’t this seem like this was just going to be a continuation of Microsoft? What was different about the foundation that made you think that this was the change that you wanted to make?

Well, I always saw the work that we were doing at Microsoft as this liberation of technology, access to knowledge for all, especially the work we were able to do in the Interactive Media Division. You didn’t have to buy the Economist to get the quality of writing of the Economist, you could log on to Slate. You didn’t have to afford Encyclopedia Britannica, you could afford Encarta. Eventually, of course, you didn’t have to pay anything for Wikipedia. I believe this liberation of the knowledge that we were holding, and the technology that we were holding, was very important. The day that I announced my departure, my colleagues from DreamWorks called and asked me to join them. We had done a joint venture with DreamWorks, and when Jeffrey Katzenberg and Steven Spielberg and David Geffen are on the phone and say, “Look, you want to come work with us,” you say yes.

So on the very day that it became public that I was leaving Microsoft, I said yes to DreamWorks to go and help them with an interesting new animated film venture that they were investing in and building up. It was at my going-away party, which was some weeks afterward, that I first began the discussion with Bill and Melinda that caused me to pull away from DreamWorks very shortly after I started there. What I heard from Bill and from Melinda was they were committed to those same reasons that I was so excited about the work of Microsoft and the work of technology, which is that they had seen that public libraries could be a bridge to access to all of this knowledge for all. But the public libraries were behind, they didn’t have the technology, they didn’t have the connections, they didn’t have the resources, and they certainly didn’t have the technical expertise to join the internet era.

When I asked Bill, “Well, how many do you want to do?” He said, “Well, I don’t know, maybe 5,000.” I said, “What if we did all of the public libraries?” He said, “In the United States or around the world?” That answer drew me to them, because I realized that the scale of their resources, their values were aligned with mine, but the scale of their resources allowed him to say just in the United States or around the entire world. That is a beautiful, beautiful asset they bring to their work, which is they can think very big in the box or out of the box, and that opportunity to help them script that, to design that, to bring the talent together, to do that. Whether it was with attaching computers and access to the internet to rural libraries in Alabama, or ultimately, if it was bringing much needed vaccines to rural areas in India and Africa and beyond. That was appealing to me, that alignment of social justice and increased knowledge, and combined with their resources that could really be transformative. Who wouldn’t say yes?

I signed on as a volunteer because I wanted to help them realize their vision, but I didn’t want to go back to the same relationship that I had reporting to Bill in the traditional fashion that I had at Microsoft. Luckily, my time at Microsoft had given me enough personal resources that I could design a job that had no income and do that with no regrets.

Was taking the money (or not) really that significant? Did it really change the nature of the relationship with your employers?

Well, we’ll go backward and say with Microsoft, I don’t think it made any difference at all, I made my money there. At Martha’s Table, I am a donor to Martha’s Table. That’s how I knew about Martha’s Table, I had been giving money to Martha’s Table, and it didn’t make a lot of sense to take money from Martha’s Table and turn around and give it back to Martha’s Table. Because then the government got part of the money in the process, and it just wasn’t necessary. At the foundation, it was really quite different, I wanted it to be a very, very clear signal that I was doing this for my friends Bill and Melinda Gates and that I was doing it as a friend and a colleague, not as a paid CEO. Did it change the dynamic? Maybe only in my head, but we were partners.

Of course, the resources came from Bill’s founding of Microsoft, but in the day-to-day leadership that I was doing, I really felt like I was a part of a family foundation structure with Bill Gates Sr. sitting 10 feet from me—and Melinda and Bill weighing in constantly on our priorities and our activities. It was a family foundation from the start, and I chose to more closely become part of that family for a period than a traditional leadership role.

In having conversations with “second actors,” in many cases, the challenges of making a switch revolve around losing an income. It puts stress on the family or even just on the person making the career switch. If you take money away from the challenges, what was your pain point in these transformations?

I don’t know if you’d call it pain point, but one of the disciplines I needed to employ was trying to figure out what was my own ambition for the use of this biggest gift I had, which was the time that I remained on this earth. That was always this teeter-totter between family and the priorities of family and being a productive member of society through work, through both pursuit of social justice and education priorities. The discipline for me was don’t take the job that people will think of as cool, as sexy, as wonderful, take the job that you get up in the morning and you can bounce into work because you’re so pleased with your ability to utilize that time. It is absolutely the case that if you take a look at how to plan out the best career, it is what can you be really great at? What are you really passionate about, and what drives your resource engine?

I steal that a bit from Jim Collin in Good to Great—that’s how he thinks corporations and nonprofits should design their own corporate strategy. But I believe that’s how you should design your personal strategy. What can you be really great at, maybe even the best in the world at? What really drives your passions? And then what do you need as a resource engine? If the answer to the first two lands you with kindergarten children, then your resource engine needs to be appropriately designed to where that constant misalignment of resources, where you’re not going to get paid very much as a kindergarten teacher, is not going to get in the way and cause that flywheel to go clump, clump, clump. You’re going to have to organize your life around that size of a resource engine. Well, that issue was taken away from me, so I really got to say what can I be best in the world at? What drives my passion? Not, say, what job would it be really cool to call my mother and tell her I got?

There were quite a few job offers and inquiries that came through that were very, very cool jobs to have on your Wikipedia page, to call your mother and tell her about. But I constantly put myself in the situation of saying: It’s 8 o’clock, you’re walking out the door to work, are you skipping? Is it the work you really want to spend the rest of the day on? I’ve been very, very lucky that my time at the foundation, at my time at Martha’s Table, in my work with the Smithsonian, and at my time at Microsoft to love the days that I had. I think that’s the most important question of all: Do you feel like that you are utilizing what you have in a way that makes you happy, as well as delivers the productivity that all of us want to see in our efforts?