Leadership Lessons From A Female Technology Entrepreneur

Victoria Montgomery-Brown advocates transparency and honesty. THE BIG THINK

Victoria Montgomery-Brown advocates transparency and honesty. THE BIG THINK

As a female chief executive, Victoria Montgomery-Brown is unusual enough. That she has reached this pinnacle in the world of technology is even more remarkable. Which means that her recently-published book, Digital Goddess: The Unfiltered Lessons of a Female Entrepreneur, is bound to offer useful insights.

Montgomery-Brown herself and her book are far too positive in outlook to dwell on the more usual complaints made by women about working in technology. But the author is not afraid to point out differences between male and female entrepreneurs and even suggests that women might have certain advantages. 

“Men are less afraid of being found out. I always think ‘deliver the bad news immediately.’ I don’t want it to come back. For me, my reputation with the people who have backed me is the most important thing. More important than making money.”

This was put to the test right at the beginning of her entrepreneurial career in 2007, when she co-founded the Big Think, the company that gives individuals and companies access to experts with content that is “significant, relevant and actionable.” The business, which started with short videos but has now expanded to include blogs and webinars, had just secured its first round of funding and was about to launch with great media fanfare when Montgomery-Brown was arrested. She says she had been doing some work for a company that she had previously worked for and was accused of using a car service without authorisation. Rather than hide the incident and hope that it would go away, she took the decision to be totally transparent and inform her investors. It was a decision she claims that has served her very well over the years since. “It has made them trust me even more,” she said in a recent interview.

Perhaps even more controversially, she also suggests that women might be more successful in leadership roles, especially when everybody is struggling, because “people are looking for people who are softer and more nurturing.” That said, she adds: “I do think women could be a bit less humble. Investors want to see confidence.” However, she cautions that taking this too far — something often associated with male executives —can cause problems, too. “Bragging or exaggerating will get you there initially. But it will come back to you in the end.”

There is a certain neatness to Montgomery-Brown publishing a book passing on tips and expertise because that is essentially the purpose of the Big Think, which she started with co-founder Peter Hopkins under the pitch “Davos democratized.” She explains: “People want to be inspired by people who have done extraordinary things.”

Indeed, it was Hopkins, a fellow Harvard graduate who began working with Montgomery-Brown on digitizing the archive of the Charlie Rose television show, who encouraged her to write the book. “He thought it would be interesting for aspiring women entrepreneurs,” she says.

This gesture is not insignificant. Many studies indicate that the most effective teams are not those composed of all males or all females but ones that are mixed. And the importance of men supporting female colleagues is also highlighted in another new book, Good Guys by David G. Smith and W. Brad Johnson. In the preface, the authors acknowledge that men need to “get better and more deliberate at mentoring women,” but add that “in order to become full conspirators in addressing bias, sexism, pay inequities and poor representation of women in leadership, men also need to become better colleagues, advocates and accomplices with women.” What follows is essentially a “how to” guide, from a male perspective, of how men can help women advance in the workplace.

And, having set out these guidelines, they come to a conclusion that would probably resonate with Montgomery-Brown. “When men are involved in creating gender parity, the outcomes in political, economic and social systems can be life-altering,” they write.


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