Boss Lady

A new way to think about career momentum


We hear and read almost daily about the conspicuous absence of women from the highest echelons of corporations, companies and countries. Women outnumber men as university graduates, enter the workforce in roughly equal numbers as men do, yet the further up the ladder you look, the fewer women you find.

A recent study from Catalyst, the non-profit research group focused on women in the work-place, revealed that women in Canada hold just 18 percent of senior officer jobs and 36 percent of management positions. Among Fortune 500 companies, women occupy only 17 percent of board seats, 14 percent of executive positions, and make up less than 5 percent of chief executive officers. Data like this are splintering the woman’s movement—think Sheryl Sandberg’s Lean In versus Anne-Marie Slaughter’s “Why Women Still Can’t Have It All.”

Much of the debate seems to swirl like a sandstorm around an insidious riddle: What comes first, having more women at the top in order to create change or making change so that women can reach the top?

I believe it’s time we look at the conundrum differently. It’s time to stop agonizing over how to affect change and to exploit the reality that profound change is already under way, a revolution in fact. Fuelled by technology and shifting demographics, digital technologies are creating a new world order that demands a new style of leader—one with attri-butes and perspectives that make women natural front- runners. That’s not just my view. That’s the conclusion from a growing body of research that finds women tend to have in spades what’s needed to lead successfully in the information age. It really is “our turn.” The question now, and one I hope to answer in these pages, is how best do we seize it?

Having worked my way up from the bottom, without the benefit of an Ivy League education or friends in high places, it’s a question I’m regularly asked. And having worked under a long list of leaders, men and women, good and bad, it’s also one I feel I can answer by sharing the hard-won lessons of my own experience. Our culture is steeped in the narrative of the self-made man; the stories of self-made women are relatively new and still unfolding, mine included. But I’ve seen enough from the front lines of power to under- stand the forces that are now redefining it. My experience has given me a unique perspective on what it takes to lead and to get ahead in our changing world, if that’s what you choose to do.


Even today, surveys find that women—even more than males—would rather work for a man than another woman. Gallup has tracked the gender preference for a male-over- female boss since the 1950s, and while it has narrowed over time, it hasn’t disappeared. It may be that women’s ongoing insecurities in the workplace have carried through the decades, making female bosses tougher on other women. Or it may be that powerful women tend to be perceived as cold and controlling as they vie for a seat at what had traditionally been a man’s table. Or it may be that people don’t want to work for their mothers. Whatever sparks it, society tends to view the gender preference as further evidence that women’s bid for equality in the workplace, specifically success at the highest levels, has faltered.


I’ve been fortunate. The professional trajectory of those early years has become the pattern of my career in media, now closing in on three decades. I’ve headed up programming at  two American networks, run a large group of Canadian channels at Alliance Atlantis, including Home and Garden Television (HGTV), and, in 2006, I was tapped to take over television at the Canadian Broadcasting Corporation (CBC). Four years later, I was promoted to what many consider the top of the broadcast food chain in Canada, executive vice-president over the entire operation of the CBC’s English Language Services, becoming, at forty-two, the youngest person to hold the job, and the first woman.

Ever since, in interviews and at talks I give, people ask me how I did it, how I managed to climb high up the corporate ladder without old money or connections. Successful men are seldom asked the same question, and rarely are they subjected to the level of scrutiny women receive when they arrive in the C-suite. For a woman, there’s always the lurking thought that she’s had some help in beating the odds, particularly if she ascends to an office no woman has occupied before. Especially when she’s a relatively young woman, who also happens to be a mother of two, as I am.


Since the fall of 2014, after Twitter asked if I would take on a bigger job as VP of Media, I’ve been heading up all our news, sports, entertainment and government-related content and activities for our partners across North America—from coverage of the Super Bowl to the Oscars, to the launch of Hillary Clinton’s presidential campaign. I haven’t slipped into the obscurity of the corporate wild. I’m playing in a wide-open field that’s dramatically changing the way the world shares and communicates. So now, when people ask for tips from my own path to success, I tell them this: My leap from the top ranks of old media to the new is emblematic of a much larger transition, one  that should give women, especially, every reason to be optimistic about their futures.


 The knowledge economy is upending business models. Hierarchical, bureaucratic management structures are dying and traditional leadership profiles are dying with them. Gone are the days where rigid leaders who issue edicts from on high through layers of management can expect the world to go their way. Now the world has a say.

With the reach of social media, and the staggering volume of credible data available online 24/7 about customers, products and the competition, today’s leaders must be keen listeners, responsive and flexible. They can’t rely on being the smartest one in the room with all the answers—the Internet gives everyone answers. The new effective leaders are those with the long-term vision to ask the right questions. They lead teams, not staff. They foster networks, not silos, creating a culture in which everyone collaborates and multi-tasking is as instinctive as breathing. So many of the qualities essential to modern leadership— anticipating events and the needs of others, listening, collaborating, multi-tasking, being flexible—are the very same characteristics that for so long cast women in the role of valued assistants, those quintessential girl Fridays. Of course, opportunity is ripe not just for women, but for anyone who wants to lead differently. (As it happens, the original “girl Friday” was actually a man, the fictional sidekick of Robinson Crusoe, prized for his loyalty and ability to take on any task.)

Revolutions never happen in isolation. Most of history’s major social shifts have come on the heels of other seismic events: the industrial revolution fuelled the growth of cities and of sickness, too, and the concept of public health was born; the Second World War brought women to the work- place en masse and sparked the second wave of feminism. Today, the digital revolution is not the only force reshaping leadership. On the horizon, a demographic eruption is about to play its own dazzling role.

As the population ages, and old boys’ clubs with it, the largest population cohort since the Baby Boom is entering the workforce with values, attitudes and expectations never seen before. Born between 1980 and 2000, the Millennials, also known as Generation Y, are projected to account for 50 percent of the workforce by 2020 and 75 percent by 2025. Companies around the world are scrambling to figure out how this new breed of worker will fit within their corporate structures. Millennials, after all, are digital natives, the first generation to reach the workplace having grown up with personal computers, smartphones, tablets and rich social media networks. They’re the engine driving the revolution, and new branches of research devoted to figuring them out. Studies find them to be liberal, well educated, racially diverse   and disdainful of traditional top-down authority. If predictions are right, they’re poised to downsize and dismantle cubicles and corner offices wherever they find them.

At the same time, the women of Generation Y are emerging as an exciting cohort within a cohort. These young women are more likely than any other females in history to have grown up with a working mother as a role model. While women of previous generations have been far less likely than their male peers to say they intend to pursue leadership roles, a 2014 research paper from the Pew Center has found that Millennial women have higher aspirations to become bosses, or managers, than females of any other age group.


Kirstine Stewart In the fraught discussions about the dearth of women in leadership roles, there’s been too much focus on reaching the top. Altitude is not the only measure of success. You can choose to be a leader in whatever work you do, at whatever level, because “leadership” is a mindset. It’s how you work: how you learn to grow and spend your personal capital. That mindset can be applied to whatever endeavour you under- take, wherever you choose to invest yourself, or whatever circumstances your life allows. Struggling to make ends meet rarely affords a woman the freedom to pursue ambitions, which, after desperation led me to the classifieds, was the first professional lesson I learned. Still, what you do with what you have can turn tides, whether you’re a girl Friday, lead a Fortune 500 company, a family, a project or yourself. It’s time to think and be leaders in life, in all its spheres.

About Kirstine Stewart

Kirstine Stewart oversaw Twitter’s North American media partnerships across all vertical channels, including television, sports, music and news. Previously, she served as Managing Director for Twitter Canada, leading Canadian operations and advertising business and partnerships. Prior to joining Twitter in May 2013, Kirstine was the executive vice-president of CBC’s English services, CBC/Radio-Canada, where she oversaw the network’s English-language radio, television and digital operations. Earlier, she was senior vice-president of programming for Alliance Atlantis, overseeing HGTV, Food Network, National Geographic, BBC Canada and others. Her new book,Our Turn, explores the qualities she believes are important for leadership—and how women are best suited to bring them to the C-suite.

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