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

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."

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