Transgender Executive: 'Just a Different Person Now Than I Was Then'

March 6, 2008 — -- Megan Wallent is an executive on the go.

At Microsoft's Redmond, Wash., headquarters where male executives far outnumber their female counterparts, Megan is a standout, especially for one significant difference. Until few months ago, she was a he.

"Well, I'm me," Megan said. "And I think most people would perceive me as female these days. And that's the way I present myself to the outside world."

Watch this story tonight on "Nightline" at 11:35 ET

But Megan used to be Michael, a longtime Microsoft executive who oversaw the entire Internet Explorer division of Windows for years, a leader of hundreds and an executive who interacted frequently with Bill Gates.

She still has her original Microsoft badge picture that was taken Aug. 11, 1996, the day she joined Microsoft.

Michael led a successful career and active social life filled with travel, an intense obsession for Boston sports teams and a beautiful house and family.

He's a Guy's Guy

Tina Dunn has been Michael's administrative assistant for seven years and says Michael gave no hint of being a man conflicted about his gender or anything else for that matter.

"He's a guy's guy," Dunn said. "He's super into sports, hiking. You know, what I consider a guy's guy. He was into all of the things that guys are into."

Michael's secret had been with him and him alone for his entire life.

"[The] feeling that I had for the longest time -- since I can remember being really small -- is that something wasn't quite right," he said. "And I didn't know what it was. I didn't know what the label was. I didn't know what the outcome would be."

It would take more than three decades for those early feelings to take hold and for him to do something about it. But Michael's secret was about to change more than just his life. He had to tell his wife.

Wife: 'I Was in Tears'

After two years of marriage, wife Anh says she had no clues about her husband's struggles. The first she knew was the day day he told her.

"I was in tears," she said.

Their marriage and their baby boy's future were suddenly in doubt. At work, Dunn was among the first to find out.

"She kind of got nervous ... and she said, 'I'm transgender and these are the things that I'm going to go through,' and I was like, 'are you screwing with me?'" Dunn said.

Then came Michael's e-mail -- addressed to his entire staff. In it, the longtime executive everyone knew as a man announced he would begin "working full time as female after the first of the year."

Michael was transgender -- meaning he doesn't necessarily relate to the gender he was born with and he was about to transform.

"I had two surgeries," she said, noting that all of her surgery was from the waist up.

"One was I had breast implants and the other one was I had what's called facial feminization surgery," she said. "My jaw is different, my ears got tucked back, my hairline got changed. I don't have a brow ridge anymore, my nose got done. My lip got changed and I don't have an Adam's apple anymore."

'I Work for a Woman'

Legally he is now a she. The sex on her driver's license has been changed from M to F, as has the name on all her legal documents.

Co-workers say the remarkable transition has been utterly unremarkable to contend with.

"I work for a woman," said Erin Chapple, one of Megan's co-workers. "You know I was actually surprised at how unconfusing it's been."

Brad Anderson is now Megan's boss. Megan switched divisions at Microsoft at the same time that she switched sexes, meaning that Anderson interviewed Michael and hired Megan.

"Actually I never even thought of it," Anderson said about Megan's sexuality. "I don't. I think I'm talking to a leader who leads a significant part of my organization."

However, there are challenges. Megan's online blog includes what she calls the "crappy look counter," a collection of odd reactions she's faced. She says she's happy to answer questions from curious strangers.

"I'd much rather have somebody be curious and ask questions rather than say, 'oh, that's really weird.' So if somebody like a stranger walks up to me and asks me questions ... good for them. I'm happy, like great, like I'm happy to meet you."

Megan Not Attracted to Men

Even though Michael spent a lifetime conflicted about his gender identity, Megan says she never wavered about her sexual orientation.

"I've never been attracted to men, never even one iota. All through my transition one of the questions that Anh and I talked about was, 'boy, are you going to all of a sudden become attracted to men? Uh, is that going to be an issue?' And I said, 'no, I can't imagine that.'"

Megan is a study in contrasts. She wears women's clothes, but no dresses or makeup. She changed her appearance, but not her voice.

"I'm not confused about it at all," she said. "It's hard to explain, but I'm not confused."

But it has been confusing to Anh, the wife who found out only two years into marriage that her husband was about to become a woman.

'It Felt Like a Betrayal...'

Megan and Anh begin each day the same way -- up before dawn for a jog with their baby son.

The one day that stands out as different was Mother's Day last year, when out of the blue Michael told Anh what he was about to do. She considered leaving him.

"I considered everything," said Anh, who paused to think whether she would have married Michael knowing this was to come.

"I don't think so," she said. "I think it would have been something that would have been hard to deal with. I mean, it's hard now. But I think I'm just a different person now than I was then."

Megan and Anh have kept their marriage together, but it is still a work in progress and there are still questions.

"It felt like a betrayal," Anh said. "But it also felt more like a secret that should have come out a lot sooner, and that this big issue that he was dealing with, that in 38 years he couldn't find someone who he felt comfortable enough to open up to and share this."

"I wasn't strong enough,"Megan said. "And I hadn't come to terms with it myself."

Megan Tells Her Kids to Be 'True'

And then there are the kids -- a baby boy with Anh and two older children from Michael's first marriage. Some might believe that he is being selfish and that this selfishness is unfair to his kids.

"Honestly, the whole selfish issue is one that I've struggled with a lot," Megan said. "And how can it be selfish and how can it be selfish and appear selfish to your children, especially, to model the behavior of being true to oneself? So we always try to tell our kids, you have to be true to yourself. You have to be who you are. You have to be honest with yourself."

Megan and Anh say they haven't lost any friends and their life is remarkably normal, considering all they've been through.

"A lot of those challenges [have] actually become a lot easier than I expected," Anh said. "I think our fears were much more, we thought it was insurmountable. But it's been actually a lot easier."

They plan on staying together -- husband and wife -- if slightly different than the way they started out.