There is still much to learn from Vista.
That thought struck me this weekend as I read a collection of old Microsoft emails and documents featuring Steve Ballmer, Steven Sinofsky and other former Redmond company executives.
The internal messages offer a glimpse into Microsoft’s decisions around the 2006-2007 release of Windows Vista (and the aftermath), with enough underlying management and strategy lessons to fill a business book.
How did I fall down this rabbit hole? Part of the blame goes to Acquired’s epic podcast series on the history of Microsoft. The latest installment, Volume II, released Sunday night, covers the years 1995 to 2014. It includes the time period, from 2002 to 2008, when I was a daily newspaper reporter in Seattle on the Microsoft beat.
It wasn’t the best of times for Microsoft, by any means.
Applying the traditional structure of a three-act play to the history of Microsoft, the “setting” would be from 1975 to 1995 (Bill Gates, Paul Allen, BASIC, MS-DOS, Windows). the “confrontation” would be 1995 to 2014 (Steve Ballmer, internet, antitrust). and the “resolution” would be 2015 to present (Satya Nadella, cloud, artificial intelligence).
But the fact that the second act was so sluggish is part of what makes it so interesting to me — especially with the benefit of knowing what happened next.
A few months ago, while listening to Volume I of Microsoft’s Acquired series, I was inspired to dig up audio from several interviews I had with Gates and Ballmer during that time frame.
After finding the audio, I offered the files to Ben Gilbert of Acquired to help with his research for the Microsoft Volume II episode. Ben and co-host David Rosenthal are known for compiling extensive behind-the-scenes material for the show, which explores the history and strategies of well-known businesses and brands.
In fact, I’m excited to have Ben join me on the GeekWire Podcast next weekend. We’ll talk about Acquired’s evolution and get their takeaways from their latest deep dive into Microsoft. We’ll also hear highlights from some of those old interviews I’ve dug up, commenting on views with the benefit of significant hindsight.
There’s one more reason I took a trip down Microsoft memory lane: Next year is the company’s 50th anniversary, offering an opportunity to review its history and take a fresh look at where it’s going. Many amazing moments from Microsoft’s past will be remembered and celebrated to mark this milestone, no doubt.
This will not be one.
While dusting off my old computers and backup drives in search of the audio of these earlier interviews, I came across a long-forgotten archive of internal Microsoft emails, memos and presentations, circa 2005-2007, that were made public in the lawsuit against the company a few years later.
This was the era of Windows Vista, one of the most difficult chapters in Microsoft’s history, when its flagship operating system was plagued by lags, bugs, compatibility issues and a general shrug of the shoulders by PC users.
The emails detail Microsoft’s decision to lower the graphics requirements for new Windows XP machines to receive the “Windows Vista Capable” designation, which signaled their suitability to run the upcoming version of the operating system.
Microsoft lowered the graphics requirements for the stated purpose (at least internally) of helping Intel “make its quarterly profits so it can continue to sell motherboards with integrated 915 graphics.”
As a result, many of the Windows XP machines that qualified for the “Vista Capable” sticker were unable to perform Vista’s signature features. Instead, they got a stripped-down version of the operating system, causing all kinds of challenges and confusion.
Looking back, internal emails offer a vivid taste of what was going on inside Microsoft at the time. Highlights include then-Microsoft CEO Steve Ballmer providing email technical support for then-Microsoft board member Jon Shirley, who was having trouble getting his scanners to work with Vista due to a lack of drivers.
Another key figure in the emails is Steven Sinofsky, the Microsoft executive who was put in charge of Windows after repeated Vista delays, and who later righted the ship with the release of Windows 7. He writes about his own problems with Windows Vista and gets some insights by listening to customers at a Best Buy.
Also included in the filing: Dell’s posthumous release of Windows Vista, which the PC maker prepared for a meeting with the Microsoft team at the time.
One of the slides below shows how hard it was to find something good to say about Windows Vista at the time.
For a more complete picture of this whole time frame, the hosts of Acquired give a well-balanced assessment in their new episode. Vista is a small piece of the conversation, given everything that happened from 1995-2014: the internet, MSN, Xbox, Tablet PCs, aQuantive, Bing, Azure, Windows Phones, Nokia and more .
I was particularly impressed by their clear-eyed take on Ballmer’s tenure as CEO – going beyond the caricature of his public persona to explain how, despite his well-documented mistakes, he guided the company through the antitrust era and set the scene for Microsoft to become an energy and cloud technology company.
In this context, the debacle of Windows Vista stickers was a moment in time. But old emails are still fun to read.
At 158 pages, there’s a lot to absorb and analyze, and in fact, there’s a bona fide Harvard Business School case study on Windows Vista, published in 2009 by then-HBS professor Ben Edelman.
But it’s 2024 after all. So as I was going back through the emails, I thought it would be fun to ask ChatGPT to read the entire file and assess Microsoft’s leadership during that time frame.
The biggest business lesson AI learned from the Windows Vista saga? The “critical importance of maintaining technical integrity while ensuring effective communication and collaboration with stakeholders.”
It’s not exactly Harvard, but it’s a concise and accurate assessment of the issues.
Read the full archive of Microsoft emails for yourself in PDF below, watch the new Acquired episode here, and check back this weekend for my conversation with Acquired co-host Ben Gilbert on the GeekWire Podcast.
