Harvard Business Review (Nov, 2010) Changing Gender On the Job

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Harvard Business Review (Nov, 2010)

Changing Gender On the Job

A Microsoft executive describes her difficult decision to “transition” at work—and the

unexpected benefits.

by Daniel McGinn

As an up-and-coming manager at Microsoft, Michael Wallent had a reputation for being a

tough boss—at times, a bit too tough. He had joined the company in 1996 and advanced

quickly; by 1999 he was overseeing a team of 300 engineers who worked on developing

Internet Explorer. Like Microsoft’s founder, Bill Gates, who met with Wallent to review his

team’s work each quarter, Wallent focused on data and facts, not employees’ feelings, and

was known for delivering withering criticism in product-review sessions. His typical

comments: “This is stupid.” “This is wrong.” “This is what you need to do.” Debra Chrapaty,

his former boss (who’s now at Cisco), says, “Michael was known to be aggressive, a little bit

condescending, harsh—he had an arrogant engineering mind-set.”

That’s in stark contrast to the style of Megan Wallent. She’s also one of Microsoft’s best and

brightest, who as a general manager ranks among the top 1% of the company’s 89,000

employees and oversees 350 engineers developing user interfaces for server software. Her

employees praise her as a boss with high emotional intelligence. She speaks softly and asks

probing questions to help them find solutions on their own. “Megan is relaxed,” says Angel

Calvo, a director of test engineering who’s been at Microsoft for 19 years. “She really thinks

about how people are going to feel about particular decisions.”

Two bosses, two styles—but only one person. In 2007 Michael Wallent told colleagues he

was transgendered, took a six-week leave to undergo breast implantation and facial

feminization surgeries, and returned to Microsoft in early 2008 as Megan. “Going through the

transition was tremendously complicated,” she says, but she tried to approach it like a

standard business problem. “I told my managers this was going to happen and that I was

going to partner with them on how to make it successful for the company.” Although her

bosses were supportive, says Anh Hoang, Wallent’s wife (and a former Microsoft employee),

the process was fraught with anxiety. “We knew this could be a careerlimiting move for her,”

Hoang says. “She’s probably one of the most senior people at any company to go through

this, so she was essentially breaking new ground.”

Looking back, Wallent says that her transition from man to woman transformed her approach

to management, which may ultimately help her career. “I’ve gotten better at my job,” she

says, “just through being more open, honest, and transparent, and learning how to better

communicate with people.”

Like many people with gender identity disorder, Michael Wallent always had a vague sense

that his anatomy didn’t match up with his sense of self. But that inner conflict stayed in the

background as he studied engineering at Worcester Polytechnic Institute, married, and moved

to Seattle to join Microsoft. By 2005 he’d had two children, divorced his first wife, and

remarried. He’d shifted from running the Internet Explorer group to overseeing a team that

helped design the look and feel of the Windows Vista operating system. In 2007, at age 38

and just two months after he and Hoang had had a child, he told her he was transgendered. A

few months later—and with her support—he decided he would transition to living as a

woman, and scheduled surgery for late that year.

A few months before the surgery, Wallent asked his boss for a meeting. Chrapaty had been

complaining about Microsoft’s struggle to recruit and hire women, so Wallent broke the ice

by saying, “Debra, I’ve decided to do something to increase the diversity of the team, and I’m

starting with me.” Although Chrapaty had helped lead Microsoft’s coalition of gay, lesbian,

bisexual, and transgendered employees, she was shocked. “I was trying to place it in the

context of this superpositioned male executive who’d just come off paternity leave with his

wife and baby,” she says. But after a moment of confusion, she offered her help.

At most companies the HR department takes charge of announcing a transition to

employees. Wallent rejected this approach.

Over the next few weeks, Wallent held one-on-one meetings with his dozen direct reports to

let them know about his coming change. (As he did when telling his family, he started with

those he expected would be most supportive and worked his way up to the harder cases.) He

sent e-mails to several key Microsoft executives, including Gates and CEO Steve Ballmer,

both of whom replied offering encouragement. Then he sent a message to all 100 members of

his team, its unusual contents flagged with a simple subject line—“Re: Me.”

Gender transitions at work remain relatively rare. Jillian Weiss, a consultant and an associate

professor at Ramapo College who’s studied the issue, says there are no reliable statistics, but

her work suggests that companies with more than 2,000 employees located in places with

tolerant populations are likely to face it at some point. Still, some transgendered employees

encounter so much resistance from coworkers that they end up leaving their jobs. (That’s a

particularly unfortunate outcome, since transgendered people typically have a harder time

finding new work, Weiss says, in part because of their appearance.) At most companies the

HR department takes charge of announcing the news to employees, usually by holding a

meeting without the transitioning worker in attendance in order to encourage a frank

discussion of concerns. Weiss compares the process to announcing a layoff. “If you’re going

to do something that creates anxiety for people, you have to give them information to ease

their sense of anxiety,” she says.

Wallent rejected this standard approach. “It was critical for me to own the communications

process,” she says, citing two reasons: First, relying on others might suggest she was

ashamed of the decision, which she wasn’t. Second, she believed that brutal honesty—and a

willingness to answer questions, no matter how personal—would shorten the time it took for

the news to stop being watercooler gossip.

The process wasn’t entirely smooth. Gender identity disorder is classified by the DSM as a

mental illness and is considered immoral by various religions. Even at a progressive

employer like Microsoft, it was inevitable that some workers would be uncomfortable with

Wallent’s transition. One employee mentioned that discomfort when he resigned, though it’s

unclear how big a role it actually played in his decision to leave. Wallent, who’d promised to

hear all employee questions, had to face some tough ones. In team meetings prior to his

surgery, he was asked whether he planned to stay married (yes), whether he was attracted to

men or women (women), how he intended to deal with his hairy arms (laser treatments), and

which bathroom he would use upon his return to work (the ladies’ room).

Although the sessions were difficult, Wallent now views them as a crucial part of her

transition. “A lot of people came back to me with these incredibly personal stories about

things that had happened to them that were equally transformative,” she recalls. Ultimately,

she thinks her new management style has little to do with the estrogen pills she takes daily.

She believes that it’s a by-product of those intimate conversations with her colleagues. “They

really brought home the value of authentic leadership, and of letting the people on your team

in to see your whole self,” she says. “It makes them more comfortable in their jobs.”

For employees who never knew Megan as Michael (now the majority of her team, owing to

job changes and the passage of time), her transition feels like a nonevent; what they know

about it comes only through secondhand observations and recollections. “I’ve heard she

speaks with a quieter voice now,” says Angie Anderson, a project unit manager who’s

worked for Wallent for two years. “People think she’s a better manager.”

But employees who worked for both Michael and Megan say they continue to notice the

change. Calvo, the director of test engineering, recalls that when Michael offered feedback on

prototype software, “people would leave the room paralyzed—‘Wow, I almost got fired’—

because of his directness, his bluntness.” But, he says, “Megan has a completely different

approach. She still comes to the same conclusion, but she drives people in a more emotional

way. ‘Have you thought about this?’ She’s becoming more of a coach, instead of a general.”

Wallent, who’d promised to hear all employee questions, faced some tough ones prior to

his surgery—such as, did he plan to stay married?

On most days, Wallent looks upon her gender transition as a closed chapter in her

professional life. Still, she continues to worry about whether she’ll “pass” as a woman while

representing Microsoft on customer visits and whether clients who recognize her as

transgendered will react badly. (So far they haven’t, she says.) There are also periodic

reminders of her unique status: For instance, she’s still officially listed as a man for HR

purposes, partly to avoid tax and legal problems.

Her worries about imperiling her career, however, seem to have been unfounded. She is

currently one level below vice president, and on the basis of her performance reviews, she

thinks she’s on track to eventually be promoted—perhaps faster than Michael would have

been, because of her evolving leadership style. Whereas Michael relied on technical expertise

as the key to his authority, Megan says her focus is people. “I want to be the type of leader

that helps people achieve their full potential, and to get the most out of them every day,” she

says. “That’s been part of my transition—learning how to lead from the people.”

Daniel McGinn is a senior editor at Harvard Business Review.