Betsy Speare: Microsoft Women Worth Watching

Betsy Speare, a Principal Program Manager Lead, is spearheading (no pun intended) the planning for future versions of Windows Server. She's the latest woman I am profiling as part of my ongoing "Microsoft Women Worth Watching" series.
Written by Mary Jo Foley, Senior Contributing Editor

In the 25-plus years I've written about technology, I've interviewed fewer than 50 female Microsoft employees (by my rough estimate). In part, this is because there are less of them. Microsoft officials say women comprise 25 percent of the company's total workforce. It's also because many of the women who do work at Microsoft are in marketing, sales and support roles and aren't among those who are "authorized" to talk to us press/blogger types.

There are a handful of women employees dotting Microsoft's executive ranks, including two Senior Vice Presidents (Lisa Brummel,head of Human Resources, and Mich Matthews, head of the Central Marketing Group). But I wanted to meet some of the less-public techies -- the engineers, product managers and programmers who work at Microsoft to find out how and why they've managed to buck the continuing trend of women not entering math/science careers. The women I've interviewed for this series have joined Microsoft via a wide variety of paths. Some knew since they were kids they wanted to be involved in technology. Others came to the Empire via a more circuitous route (master of fine arts in poetry, anyone?). Some are Microsoft lifers. Others are recent hires.

On March 24, Ada Lovelace Day -- which is dedicated to celebrating the achievements of women in science and technology -- I kicked off a new series profiling some of these Microsoft women worth watching. Over the next couple of weeks, I'll be running profiles of ten of them on my blog.

Today’s Microsoft Woman Worth Watching: Betsy Speare

Title: Principal Program Manager Lead, Windows Server

What’s Your Typical Day Like? Speare's day starts between 7 and 8 a.m., when she checks her e-mail in the kitchen while her daughter eats. She spends the rest of her day talking with people and doing all kinds of planning for the next version of Windows Server. She deals with the Server and Tools Business general managers, technology owners and individuals interacting with customers and partners. "It's lots of e-mail and lots of meetings," Speare says.

Did you always want to be involved in technology? If not, what steered you this way? In high school, Speare was into computers. She took Apple IIe programming classes and was almost always the only girl, she says. "I was always the 'person who knew how to work the computer' in various job settings.

Speare entered Eastern Washington University as a computer science major. "I knew when I started my degree that I was going to come to Microsoft," Speare said. A self-described "late bloomer," Speare graduated from college at 26, after traveling for a while in the U.S. and Europe. She credits her mom, "an amazing go-getter who believed women can accomplish whatever they want" as someone who encouraged her she didn't need to have her whole career path figured out from early-on.

Speare had sold PCs and Macs while still in college and developed an interest in multimedia software at that time. After contracting for Microsoft for six months, she joined as an SDET (software development engineer in test). She worked on the Exchange Server team, writing build scripts, and later moved into a test and test lead role, owning deployment and directory integration with Exchange 2000. She then moved to Windows Server and became the product management lead on Windows Small Business Server team. "I learned about design, how to write specs for a time, and how to get people on board while you're planning," she says. For the last four years, Speare has been working on the Windows Server 2008/2008 R2 team and is currently running the planning for "future versions" of Windows Server.

Advice for women (and/or men) considering a career in technology? "I have a foundational belief that you should enjoy what you are doing" and not just do things you're not keen on in order to be able to do other, more preferable things in the future, Speare says. "Former Windows Senior Vice President Brian Valentine used to say if you weren't happy to jump out of bed and come in, you're doing the wrong thing," she recalls. First and foremost, you need an understanding of what gets you excited, Speare says. "For me, it was the translation of inaccessible technology into something that is easily accessible."

Favorite gadget (just one) or technology: It's a toss-up between her Windows 7 ThinkPad and her Braun hand mixer. (I'd say the ThinkPad might have a slight edge, thanks to Windows 7. "This is the first time I haven't said, 'I hate this thing,'" she says of her laptop.)

Betsy Speare has seen a lot of changes, both technical and cultural, at Microsoft, since she first joined the company in 1986.

Like a number of other of the "Women Worth Watching" whom I've interviewed as part of this blog series, Speare says she was attracted to Microsoft because she wanted to work on something that was going to make a difference in peoples' lives, She recalls how she felt when she was part of the Exchange team and heard U.S. astronauts were going to use Exchange mail to communicate with their spouses -- something that had been done before via public radio. She says she feels the same kind of thrill when she hears about someone using Windows Server to handle a micro-finance project or some other task that has a major positive impact.

Speare has seen a shift inside Microsoft from doing technology for technology's sake, to "genuinely trying to understand the voice and the needs of the customers and partners," she says. "It used to be that you had discussions with technology owners about features, not scenarios," she says. But since the completion of Windows 7/Windows Server 2008 R2, that has changed.

"At the end of our Windows Server 2008 work, we started working more closely with (Windows) client, and the influence has gone both ways," Speare says. Windows Client leadership has thought through the engineering process, while Windows Server has focused a lot on customers and partners, she says. Going forward with the next version of Windows Server -- about which Speare is not at liberty to discuss, she says -- "it's about how you get things done vs. what you get done."

Another commonality the Windows Client and Server teams have is the relative paucity of women in engineering and managerial roles. On the Server and Tools Business (STB) side of the house, there's a realization of that fact and attempts to remedy the situation, Speare said. In STB, there's a Women's Leadership Council, which kicked off around 2002, designed to help women in Windows Server find each other, make connections and share experiences.

The focus was on making the playing field more level, Speare says. Currently that group has more than 200 women -- so maybe there will be some more women representing in an official capacity Microsoft's Windows business in the not-so-distant future.

(Check out all the Microsoft Women Worth Watching profiles here.)

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