A couple of weeks later, Ballmer called me in and proposed that I transfer over to manage Windows. Sounds like a plum job right? Well, that wasn’t so obvious at the time. Windows had been announced the previous year with much fanfare and support from most of the existing PC vendors. However, by the time of my discussion with Steve, Windows still had not shipped within the promised timeframe and was starting to earn the reputation of being “vaporware.” In fact Ballmer had just returned from what we internally referred to as the “mea culpa” tour to personally apologize to analysts and press for the product not having shipped on time and to reinforce Microsoft’s definite plans to complete it soon.
Further, Microsoft’s strategy to get IBM to license Windows had failed. IBM had rejected Windows in favor of its own character-based DOS application windowing product called TopView. With IBM still the dominant PC seller, Microsoft would have to market Windows directly to IBM PC users. It would be the first time the company sold an OS level product directly to end-users (unless you count the Apple SoftCard, a hardware card that enabled Apple II users to run CPM-80 applications on their Apple IIs, which I had also previously managed). Since I had been the product manager that had the most experience with marketing technically oriented products through retail channels (rather licensed to PC vendors), Ballmer thought the job might be a good fit. In addition, he pointed out that since Windows was intended to expand the appeal of PC through its easier-to-use graphical user interface, it should appeal to my more end-user product experience and interests.
At that point Windows was no longer considered the company’s star project, as it had become a bit of an embarrassment. Even internally there were doubts among some in the company that Windows would ever ship. Also, because Ballmer had already burned though four product managers to try to get there–people who now had been either reassigned or were no longer at Microsoft–the product was developing a reputation for career death. Apparently prior to offering the job to me, Ballmer had tried to persuade Rob Glaser, already recognized as a bright, up-and coming talent, to take the position. But Glaser turned him down. When Glaser heard that I was offered the position, he even stopped by to counsel might that it would be a bad career move.
This made me think that perhaps the offer to me was a ploy by Gates and Ballmer to fire me because of their disappointment in dealing with Turbo Pascal and my suggestion that perhaps my assignment to managing programming languages was a poor choice on their part. It seemed clever: give me a task that no one else had succeeded with, let me fail as well, and they would have not only a scapegoat, but easy grounds to terminate me. So, I confronted Gates and Ballmer about my theory. After their somewhat raucous laughter they regained their composure and assured me that the offer was sincere and that they had confidence in my potential success.
So, in January of 1985 I transitioned over the Windows team, but even as I assumed my new role, I discovered that the Windows development architect and manager, Scott McGregor, a former Xerox PARC engineer, has just resigned. Ballmer himself took up McGregor’s role as the development lead in addition to his other responsibilities.