Business lessons from Windows Vista: Insights from a forgotten trove of internal Microsoft emails

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Business lessons from Windows Vista: Insights from a forgotten trove of internal Microsoft emails Todd Bishop
Windows Vista’s launch in late 2006 and early 2007 was one of the toughest chapters in Microsoft’s history.

There’s still a lot to learn from Vista.

That thought struck me this weekend as I was reading through a collection of old Microsoft emails and documents featuring the likes of Steve Ballmer, Steven Sinofsky, and other former executives with the Redmond company.

The internal messages offer a glimpse into Microsoft’s decisions surrounding the 2006-2007 Windows Vista launch (and the resulting fallout), with enough underlying management and strategy lessons to fill a business book.

How did I fall into this rabbit hole? Part of the blame goes to the Acquired podcast‘s epic series on Microsoft’s history. The latest installment, Volume II, released Sunday night, covers the years 1995 to 2014. This includes the period of time, 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 stretch.

Applying the traditional structure of a three-act play to Microsoft history, the “setup” 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 such a slog is part of what makes it so interesting to me — especially with the benefit of knowing what happened next.

A couple months ago, while listening to Volume I of Acquired’s Microsoft series, I was inspired to unearth the audio from several interviews that I had with Gates and Ballmer during this timeframe.

After finding the audio, I offered the files to Acquired’s Ben Gilbert to help with his research for the Microsoft Volume II episode. Ben and co-host David Rosenthal are known for gathering extensive background 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 his takeaways from their latest deep dive on Microsoft. We’ll also listen back to highlights from some of those old interviews that I dug up, opining on them with the benefit of considerable hindsight.

There’s one more reason I’ve been going down Microsoft memory lane: Next year is the company’s 50th anniversary, offering an opportunity to reconsider its history and take a new 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.

In the course of dusting off my old computers and backup drives, searching for the audio of those past interviews, I stumbled across a long-forgotten archive of internal Microsoft emails, notes, and presentations, circa 2005-2007, that were made public in a lawsuit against the company a few years later.

This was the Windows Vista era, one of the toughest chapters in Microsoft’s history, when its flagship operating system was plagued by delays, bugs, compatibility problems, and a general shrugging of shoulders from computer users.

The emails are a detailed record of Microsoft’s decision to reduce the graphics requirements for new Windows XP machines to receive the “Windows Vista Capable” designation, which signaled their suitability to run what was then the upcoming version of the operating system.

Microsoft lowered the graphics requirements for the expressly stated purpose (internally, at least) of helping Intel “make their quarterly earnings so they could continue to sell motherboards with 915 graphics embedded.”

As a result, many of the Windows XP machines that qualified for the “Vista Capable” sticker were unable to run Vista’s signature features. Instead, they got a stripped-down version of the operating system, causing all sorts of challenges and confusion.

Looking back, the internal emails offer a vivid glimpse of what was happening inside Microsoft at the time. Highlights include then-Microsoft CEO Steve Ballmer providing tech support via email for then-Microsoft board member Jon Shirley, struggling to get 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 brought in to lead Windows after Vista’s repeated delays, and who later righted the ship with the Windows 7 release. He writes about his own problems with Windows Vista, and picks up some insights by listening to customers in a Best Buy.

Here’s a page of notes in the filing from an unidentified executive, outlining the challenges of Microsoft’s two-tiered approach to the Windows Vista versions. I wasn’t able to figure out from the court documents whose these were. If anyone recognizes the handwriting, let me know.

Also included in the filing: Dell’s Windows Vista launch post mortem, which the PC maker prepared for a meeting with Microsoft’s team at the time.

One of the slides below shows just how hard it was to come up with something good to say about Windows Vista at the time.

For a more comprehensive view of this whole timeframe, the Acquired hosts give a well-balanced assessment in their new episode. Vista is a small slice of the discussion, given everything that happened from 1995-2014: the internet, MSN, Xbox, Tablet PCs, aQuantive, Bing, Azure, Windows Phone, Nokia, and on and on.

I was struck in particular 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 missteps, he guided the company through the antitrust era and set the stage for Microsoft to become an enterprise and cloud technology powerhouse.

In that context, the Windows Vista sticker debacle was one moment in time. But the old emails are still fun to read.

At a whopping 158 pages, there’s a lot to absorb and analyze, and in fact, there is a bona fide Harvard Business School case study about Windows Vista, published in 2009 by then-HBS professor Ben Edelman.

But this is 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 filing and assess Microsoft’s leadership during this timeframe.

The biggest business lesson that the AI gleaned 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 succinct and accurate assessment of the issues.

Read the full archive of Microsoft emails for yourself in the PDF below, see the new Acquired episode here, and check back this weekend for my discussion with Acquired’s co-host, Ben Gilbert, on the GeekWire Podcast.

Internal Microsoft emails – Windows Vista by GeekWire on Scribd

https://ift.tt/IytzUDM July 23, 2024 at 02:20PM GeekWire
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