Klawe pointed to the recruitment of Peggy Johnson from Qualcomm as head of business development in September as a recent success, but she conceded there have been backward steps, notably the ousting of Tami Reller and Julie Larson-Green, who ran the flagship Windows unit until a shakeup in 2013.
"I did feel badly that we had Tami and Julie on the executive team and then had two fewer people. But it really had to do with what made sense in terms of who was the right person for which job," said Klawe. "I'm sure we'll see more women in those levels."
Reller has since left Microsoft, while Larson-Green is responsible for the overall look and feel of Microsoft's software services.
Microsoft has never been a beacon of diversity.
Karin Carter, who worked at the company in its heyday from 1983 until 1997 and went on to write a book about the experience, said there were only five or so women programmers at Microsoft when she joined, with the vast majority of women in support positions.
"The first time my fellow administrative assistant and I worked all night to get materials ready for a meeting, we got roses from the vice president of the international group," said Carter. "My first thought was, 'Roses? How about money?'"
Today the numbers are slightly better. Microsoft's 15-strong senior leadership team, which runs the company day to day, has three women: Chief Financial Officer Amy Hood; Lisa Brummel, head of human resources; and recent hire Johnson.
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Its board of 12 also has three women: former Wall Street banker Dina Dublon; Klawe, president of Harvey Mudd College; and most recently Teri List-Stoll, chief financial officer of Kraft Foods Group.
But the issue of unequal pay looms large.
Numbers from job site Glassdoor show that men tend to earn more doing a similar job than women at Microsoft, though the data is far from complete and based on voluntary disclosure.