Showstopper! the Breakneck Race to Create Windows NT and the Next Generation at Microsoft

What does it take to make great software? A focus on quality bordering on obsession, brilliance, long hours, personal sacrifice, and a leavening of that intangible called leadership. Showstopper stands beside The Mythical Man Month and The Soul of a New Machine in its depiction of programming and technology around the creation of The Last Great OS.

Lead Engineer David Cutler and his team had an ambitious job, to make the first ‘platform-independent operating system’, a piece of software which would revolutionize personal computing by adding reliability and backwards compatibility, and make Microsoft very very wealthy. Over 4 years, they transformed a vague idea into working software, at the cost of $150 million, many broken marriages, and constant abuse and bullying. The sense I got from this book is that Cutler was a maniac, but perhaps the only type of person who could make something like NT work. I can only hope that the massive stock options the team got compensated them for the emotional trauma. The human side is paramount in this story, but able analogies explain the inner workings of the PC.

These days, post-Zune, Windows phone, and the resurgence of Apple it’s easy to mock Microsoft as a has been-a dinosaur limping along on monopoly market power and tech lock-in. But it serves us to remember that they were agile and innovative once. Cutler’s messianic vision may have been justified, because 20 years later his code is still at the heart of the versions of Windows that we use.

*Disclosure: Gregg Zachary is a friend and colleague.