Mike Maples Sr., 1942-2025: Microsoft’s ‘adult In The Room’ Had A Deep Impact On The Company

Mike Maples Sr. led Microsoft’s applications division in the late 80s and early 90s. (Photo courtesy Maples family.)

Mike Maples Sr. faced no shortage of skepticism when he joined Microsoft in 1988, after being personally (and persistently) recruited by Bill Gates to succeed the Microsoft co-founder as the leader of its applications division.

A tech veteran with two decades of experience at IBM, Maples was an outsider at the scrappy software company in Washington state — a status that was formula for failure for numerous execs brought in by Microsoft over the years.

Maples turned out to be an exception.

“Not many outside hires into exec roles at Microsoft worked out. Mike came from IBM, which was just what Microsoft didn’t want to become. But Mike was different,” recalled Brad Silverberg, who led Microsoft’s systems business, including Windows, for much of Maples’ tenure. “He succeeded in a most profound way.”

As the leader of Word, Excel, and other Office programs, Maples “shaped that division in ways that exist today,” Silverberg explained. “He is often said to have been the adult in the room. He was older and wiser than the rest of us. He led by example of how we all wanted to be as leaders and execs.”

Maples, who left Microsoft in 1995, died this week in Austin, Texas. He was 82.

Gates this week remembered Maples as “an extraordinary human, business leader, and friend.” He added, “I’m lucky to have known him, and I’m thinking of his family during this difficult time.”

Maples was “one of the kindest, most level-headed, serious businessmen,” said Steve Ballmer, the former Microsoft CEO, who led worldwide sales and support during Maples’ tenure. “He made a real difference in getting our applications business organized and together. … We owe him a lot.”

Mike Maples in The Seattle Times in October 1988, a few months after he joined the company. (Clipping via NewsBank, Seattle Public Library)

Born and raised in Oklahoma, Maples received a bachelor’s degree in electrical engineering from the University of Oklahoma in 1965 and an MBA from Oklahoma City University in 1969. After U.S. military service in Vietnam, he began his career at IBM, where he held various leadership positions before joining Microsoft in 1988.

As he explained in a 2004 oral history interview conducted for the Software History Center, Maples had gotten to know Gates in his role at IBM. Maples and Gates were responsible for the companies’ respective keynotes during an extended roadshow promoting IBM’s OS/2 operating system, on which Microsoft was partnering at the time.

Toward the end of the tour, Gates asked Maples if he’d like to come work at Microsoft. Initially, Maples declined, describing himself as overpaid and telling Gates it wasn’t a good idea to poach an exec from a partner.

A few months later, Gates offered again. Maples was inclined to decline again, until his wife, Carolyn, asked him why he wasn’t making the move.

“And I got to thinking about it, and I really didn’t have a very good reason,” Maples recalled in the 2004 interview. Ultimately, he said, “I decided that being a big fish in a little pond was better than being a little fish in a big pond. I certainly didn’t envision Microsoft dominating IBM. IBM was the power center and Microsoft was a little supplier.”

At the time, the differences between IBM and Microsoft were stark, a fact that sunk in for Maples when he went to the first Microsoft company picnic in 1988.

“There were only two children,” he recalled. “Microsoft had 1,800 employees and there were only a couple of them that were married. You had all these young kids who weren’t married and were right out of school. IBM had conventional dress codes; Microsoft — it was very much like a college campus.”

In this environment, Maples saw opportunity to make an impact, as he explained in 2004:

“I think the good thing for me, coming into Microsoft, was that it was pretty much a blank slate. There were virtually no development processes; there weren’t organizations; there weren’t ways of doing things. It was just a bunch of kids struggling to figure out how to do things.

“I decided early on that my approach was going to be non-prescriptive. I didn’t want to tell them that this was the development process or this is the way you should do things. So what I did with each of the organizations was to say “I don’t think it matters what process you use; I just want to make sure you use a process, that it’s not a random walk.”

Jon DeVaan, who was a longtime Microsoft executive and engineering leader, recalled how Maples made an impression after arriving at the company.

“At the first all hands meeting after he was hired, he played with the notion that he was from IBM coming into a notoriously informal hacker culture. He had slides, of course, and the last agenda item said, ‘Dress Code.’ This sparked some anxiety, but he was just messing with us, displaying his excellent sense of humor.

“Mike brought professional management ideas to Microsoft and improved accountability from top to bottom. The first way he did this was to create product units that had end-to-end responsibility for the success of their app. It drove end-to-end understanding of customer needs and market results in the teams. He was also instrumental in building career development and mentorship capabilities to grow the quality and capabilities of everyone.”

One of the beneficiaries was Mike Slade, a product marketing leader at Microsoft at the time who went on to become CEO of Microsoft co-founder Paul Allen’s Starwave venture. Slade served in leadership and advisory roles with Steve Jobs at NeXT Computer and Apple, and founded VC firm Second Avenue Partners.

Slade this week remembered Maples for his subtle but powerful approach.

“Mike was an amazing mentor during the ‘angry young man phase of my career. He offered wise counsel and common sense insights, rare commodities in late-80s MSFT culture.

“One time I was complaining about not advancing fast enough and he said to me ‘careers are long’. At the time I thought it was an incredibly obvious and useless insight. Over time I came to appreciate the fundamental wisdom in that short, elegant phrase and (of course) reused it over and over again as I became a senior manager and then a CEO.

“He will be missed. A class act and such a fun and nice guy. “

Ballmer, Maples, and Microsoft finance chief Frank Gaudette formed Microsoft’s Office of the President upon the 1991 retirement of Jon Shirley as president — known internally as the “BOOP,” for “Bill and the office of the President.”

Gaudette’s death in 1993 from cancer had a deep impact on Maples. In the 2004 oral history, Maples recalled attending Gaudette’s funeral at the time.

“There was some comment about how much he loved his kids and how much time he spent with them, but I knew he was working like me − 15 hours a day, 6 or 7 days a week.

“I had made a list of things I wanted to do before I died: go to Africa, Alaska, China − a number of things. My wife and I had had very few vacations. I’d had 4 vacations in 20 years or so. So I knew I had really short-changed her. So we decided that in 1994 — Windows 95 was about to ship, Office 95 was about to ship — that we’d finish those products and if I stayed, then we would be working on the Internet strategy and it was going to be a 3-year release cycle for the next set of products. So if I was going to stay I needed to stay from 1995 through 1998.

“So I looked at my age and my health, and I said, “If I’m not careful, I’m going to be doing these life tasks in a wheelchair or something’s going to be seriously wrong, and I really need to think about doing them and being more healthy.”

After leaving Microsoft, Maples became a rancher in Texas, while checking many of those life experiences off his list. He continued to mentor entrepreneurs and business leaders, offering his unique brand of wisdom and guidance.

Maples’ son, Mike Maples Jr., a Silicon Valley-based entrepreneur and venture capitalist, this week described his dad as “a mentor, a friend, and one of the greatest inspirations of my life,” in a post on X.

“He showed that it’s possible to be both powerful and kind, serious yet able to laugh at yourself,” Mike Maples Jr. wrote. “He was fiercely committed to success, but he pursued it in a way that honored the spirit of true greatness — winning not for the sake of winning at all costs, but for the sake of doing things the right way.”