The dream boss? What it was like to work for Bill Gates

This is part three of a series of stories by Robert Gaskins who helped invent PowerPoint at Forethought Inc. in 1984 (see part one and part two). It was the first significant acquisition made by Microsoft. We spoke to Robert about the process of building a startup in the 1980s and what life was like negotiating with, and working for Microsoft. After the sale Robert reported directly to Bill Gates, heading up Microsoft’s business unit in Silicon Valley. He managed the growth of PowerPoint to $100 million in annual sales before his retirement in 1993.

This post looks at what it was like working with Bill Gates, including being grilled by him in an pre-acquisition interview, working closely with him, and the insights Gates bought to running Microsoft in the early days of its’ existence. 

Here’s Gaskins in his own words…

The Interview

One of the explicit conditions of the Microsoft offer to acquire Forethought was that I had to pass a full-blown interview by Bill Gates (I was the only person singled out in this way). So when the acquisition discussions were under way, I went up to Redmond alone, and met with Bill in his office, one-on-one, for a couple of hours. We had had a number of business meetings before, so we knew each other slightly.

Bill Gates 2Even so, it certainly concentrates the mind to be personally interviewed by Bill, with the whole $14 million acquisition and the best chance of liquidity for our investors and financial reward for our employees all riding on his evaluation.

Bill had a normal conversation with me, probing me about technical details of our software and the Mac platform, about marketing positioning and plans, about business numbers and ratios, and about individual employees. It went very well, since I had all those areas at my fingertips. I had just written my history of the company’s restart in the prior two weeks, I prepared all the business plans, I lived and breathed the technical details, and I had had six weeks to recover from the first customer ship.

I didn’t expect anything different, but just for the record, Bill did not ask me:

  • Why manhole covers are round
  • How many gas stations there are in the U.S.
  • Whether I could code FizzBuzz in a language of my choice on the whiteboard.

We just had a perfectly normal and pleasant conversation, all of it at the enhanced level of intellectual intensity characteristic of Bill. I came away feeling that things had gone very well.

By Monday, two days later, word came in a telephone call that Bill had approved me and was in agreement with the deal, but was leaving the details of that deal to others.

Working with Bill Gates

After the acquisition, I worked a lot with Bill. For the first year after the acquisition, I reported directly to Bill, in his role of Acting VP of Applications. Then Bill hired the great Mike Maples to replace Bill VP of Apps, but I still saw Bill and talked with him often.

gates1.png
Microsoft Applications Division Management Circa 1989. (Mike Maples, VP Apps, and his direct reports). Seated, from left: Jeff Raikes, Bob Gaskins, Pete Higgins, Mike Maples, Susan Boeschen, Tandy Trower. Standing, from left: Charles Stevens, Peter Morse

Bill very often came down to Silicon Valley to review PowerPoint progress, because he considered it an important product, and because (since we were the only development group outside of the Redmond campus) he heard less about us in hallway conversations.

We would go over every detail of the code and of the business plan with Bill, and he would give us feedback on everything. This was extremely valuable; there was virtually never a time when Bill had an opinion that we thought was wrong. And Bill had in mind every detail of all the other Microsoft applications, of all of our competitors’ applications, of the various operating systems (Mac, Windows, OS/2), of all the personal computer hardware shipping or forthcoming, and of how actual customers were using all of these, so he could offer informed opinions and specific facts that were invaluable in our planning.

Bill especially was a perfect master of judging when a piece of software was adequate to ship.

He would personally review our specs, try our builds, and try our competitors, and tell us very frankly whether he thought the product concept was adequate and whether the implementation was sound enough to ship. He didn’t try to make the decision for me, but there was no one whose opinion we took more seriously.

Gates’ skills

In short, Bill Gates was just the perfect hands-on technical guru to be my boss. Things got even better when he hired Mike Maples, because Mike also knew how to manage thousands of people in a deep multi-level organization and get things done. The combination of Bill and Mike, during the first years after the acquisition, was an ideal context for success.

bil-gates-4Part of Bill’s secret was that he had a healthy respect for decentralized knowledge. He had a strong opinion on everything, but he didn’t ignore other opinions. At the Apps Division’s executive staff retreat in early April 1989, there was a discussion of the outcome of having reorganized the division into business units the preceding September. There were still some authoritarians who thought it was too messy to have all these independent units doing different things in their own ways.

Bill had the right comeback, immediately:

“We don’t lack the power to enforce our decisions; we lack the information about what we should require.”

The Microsoft system of the time allowed our group to make repeated course corrections and get to the right final result for our product, while other products at the same time made different calls.

Gates’ belief in PowerPoint

The first breakthrough version of Windows was version 3.0, shipped in May of 1990; PowerPoint’s new version 2.0 shipped the same day, and Bill Gates used PowerPoint to demonstrate what the new Windows could do. Both Windows and PowerPoint started flying off the shelves.

Two years later, in April 1992, the next version of Windows (version 3.1) introduced proper typography and TrueType fonts. PowerPoint had contributed a great deal to that, and again a new version 3.0 of PowerPoint was shipped on the same day as the new Windows, again Bill Gates used PowerPoint to demonstrate the huge improvements in Windows and again sales blew away all expectations.

Bill Gates 3.png

With these two versions of Windows and of PowerPoint, Windows PCs began to outsell Macintoshes by large multiples: from ten times as many (1992) to twenty-five times as many (1997) to fifty times as many Windows machines as Macintosh machines sold (2003). The success of Windows was crucial to PowerPoint, but the success of PowerPoint was also crucial to Windows.

Bill Gates was my direct boss for the first year after the acquisition, so we saw a lot of each other. It was a great experience.


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This is the last in a series of stories from our interview with Robert Gaskins. Why not check out the other posts in the series:

Image credits:
Bill Gates with floppy disk – adapted from https://flic.kr/p/7BFWkj
Bill Gates with hand on chin – https://flic.kr/p/7BFWkj
All other images are sourced from Robert Gaskin’s excellent website covering the history of PowerPoint. His book “Sweating Bullets” remains the definitive read on that topic.

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