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“I’m committed to getting more women into leadership positions”

A portrait shot of Diane Flynn in front of a soft grey wall. She has a blonde bob haircut, wears a white shirt and a dark blue cardigan, and she smiles into the camera.
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Diane Flynn encourages women leaders who have put their careers on hold to pick up where they left off.

Start-ups and established companies alike have long been knocking at Flynn’s door. As the search for women leaders picks up speed in Silicon Valley and elsewhere, they’re seeking Diane’s expertise in the matter. The entrepreneur has a clear goal: she wants to show the world that they’re missing out on an extraordinary talent pool – women who’ve paused their careers, typically for caregiving. These women are increasingly wanting back in, but lack of confidence, skills, and connections can often be limiting factors. As co-founder of the company ReBoot Accel in Menlo Park, California, she is taking up the task of helping these women refocus on their careers by offering coaching that makes this process as simple as possible. She now even counts a few men among her clientele, and also helps companies and private equity firms with gender diversity at all levels.

Diane, I’d like to start by posing a question that rarely gets answered. Why do men get ahead much faster than women in Silicon Valley? And why are they typically the first to be backed by investors?

Much of this has to do with networks. Men, by virtue of having more peers at senior levels, have more built-in networks. Many golf, fish, and grab drinks together. When women are “onlys”, they are often not included in these informal gatherings. Because of this, they don’t get the same type of mentoring, sponsorship and support. I believe that often hurts their advancement. The same goes for the investment community – it’s easy to support people you trust and who you believe have potential. The unconscious and sometimes conscious biases that exist hurt women seeking funding.

Who influenced your personal leadership style and sense of entrepreneurship?

Definitely my father. He was a very successful businessman and was exceptionally qualified to lead a team. I also had two brothers who did well in their careers very early on. My first priority for many years was to be a mother. But when my kids were older, I felt compelled to relaunch my professional life. I don’t think there’s a right or wrong way to parent – and most people have to work to finance life – but I’m working to create more options and pathways for women to fluidly move in and out of the workplace. Growing up in the ’70s, I didn’t have many role models because there weren’t many women in leadership positions. That has changed dramatically, though not nearly enough. We no longer have to go it alone; there are many successful women entrepreneurs to serve as role models.

“Companies are in dire need of getting more women into leadership positions.” Diane Flynn

But isn’t the reality much different, especially in Silicon Valley? Why do we still hear so few names of women CEOs?

My experience is that more and more companies want to hire women, but they often cite a “pipeline problem”. I believe there are plenty of qualified women, so perhaps this is true. Requiring diverse slates and removing unconscious bias in the hiring process is a good start. Some executives have told me that they are desperate to find women engineers, particularly in Silicon Valley. Most companies try a number of ways to achieve meaningful gender diversity, but research suggests most of these initiatives fall far short. I’m hopeful we’ll see that trend grow considerably in Europe.

What do you do exactly with your company ReBoot Accel?

ReBoot Accel is a platform for women who, for one reason or another, have put their careers on hold, yet are interested in resuming their professional lives. I’m committed to getting more women into leadership positions. Companies are in dire need of this. I also consult companies on ways to create workplaces where women at all levels thrive.

A portrait shot of Diane Flynn, with the background out of focus. She looks into the distance and smiles. Diane wears a white shirt, a dark blue cardigan and a long necklace.

When planning their careers, do you think it’s important that women are not intimidated? This means having the courage to say “yes” to jobs and opportunities that may seem a bit overwhelming at first. Would you advise your clients to take the leap?

Absolutely. I’m constantly doing things that I’ve never done before. I start with “yes” and then get resourceful on how to deliver. I believe the most effective approach is to assemble a strong team of positive, capable and “can-do” talent.

What does a team like this need?

I’m a strong believer in a multi-generational workforce. Combining wisdom with fresh perspectives results in innovative and powerful thinking. The 30-year-olds at my company come up with new ideas that greatly contribute to our success, and those of us with more experience can offer pattern recognition and wisdom.

Are there even big differences between male and female leaders anymore?

Yes, research suggests women lead very differently than men. I don’t think one is necessarily better, although women were ranked stronger leaders in nearly every category in recent research. But I believe having a gender mix results in the best workplaces.

“The only way to really understand the world we live in is if every voice is heard.” Diane Flynn

Is anything else still gender-specific?

Parental leave. If men don’t take it, women suffer.

In addition to gender diversity, having a diverse mix of nationalities is becoming an increasingly important asset for a team. Many say that this makes the team more creative and stable. Do you agree?

Smaller companies have to start asking themselves this question more and more. I’ve noticed that larger companies tend to be better at this. In many cases, ignorance towards the issue of diversity has its roots in the company’s beginnings – how the company recruited its first employees and where they come from. When entrepreneurs stick to hiring people from their trusted network, they often don’t know how to confront this issue. I recently attended an event Google held for women in tech with around 350 other people in Santa Cruz. The manager there told me that the team strategies in the pipeline are specifically designed to ensure that more women are hired and there is more diversity within teams – because the only way to really understand the world we live in is if every voice is heard.