Twitter VP Kirstine Stewart on what comes after “leaning in”

Twitter's VP of media talks about her new book, supporting women in the C-suite, and why she has no plans to run for office

Twitter vice president of media Kirstine Stewart

Twitter vice president of media Kirstine Stewart. (Portrait by Rodrigo Daguerre)

In 2013, Kirstine Stewart made national headlines when she announced her departure from CBC, where she oversaw the network’s English-language operations, to join Twitter Canada. It was Stewart’s first venture away from traditional broadcast media, after a career that included stints at Alliance Atlantis and the Hallmark Channel. At Twitter, she’s applied her knack for connecting brands with audiences and, last year, was promoted to vice president of North American media. 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.

You’ve worked at a number of places that could have provided fodder for a tell-all memoir, from Alliance Atlantis to CBC and now Twitter. What made you decide to write Our Turn, about what you see as the incredible potential for a new generation of female business leaders, instead?

I get invited a lot to do speeches to groups, and I’m always asked questions about being a woman trying to make things work today. Women always want to know, “How do you do it?” or “How did you get here?” as though there’s some kind of blueprint or secret. One of the questions I get asked the most is, “Can I have babies? What will that do to my career?” And I’ve always tried to explain that there is no one direct path. The best way to achieve success for yourself is to figure out what it means to you and work on things that actually match your strengths. So instead of being a prescriptive book that says, “Follow these steps and this will happen,” it’s more like, “Open your mind to the possibilities and the fact that there might be more opportunity today for a different kind of leadership than there was in the past.”

You describe these new essential traits of leadership as anticipating the needs of others, listening, collaborating, multi-tasking and being flexible—and you point out that while women typically possess them, they’re often relegated to the role of valued assistants and Girl Fridays. How do you see these skills becoming more important?

Some of the traits that [women] may have been trying to hide or didn’t think were as valuable before are actually incredibly valuable today, given how the world has changed and how people expect companies to run with a much more open, understanding and outward-facing attitude. I think that presents opportunities for people—women and men—who hadn’t necessarily seen pathways to success before.

How does your book differentiate from, say, Sheryl Sandberg’s Lean In?

Lean In is fantastic for reminding women that they have to speak up—and that it’s time for partners and families to do more to help a woman’s career. And I agree with all that. My book is more for women who say, “Well, how do I lean in, and what do you mean by that, and maybe I don’t feel confident enough to lean in.” What I’m saying is, I’ve been there too, and I don’t always know when to lean in either. And I sometimes find it difficult, so here’s what I did to get myself to the place I needed to be to do what I do today. And I try to remind people that you don’t have to actually be CEO—your success is where you want to find it and at whichever level you want to be.

Your notion of success hasn’t always been universally admired. You drew criticism for returning as president of Paragon International six weeks after your daughter was born.

Yeah, I think that showed a bit of my naiveté early in my career. I would do interviews and say, “Yes, I’ve come back to work full time six weeks after having the baby.” There were certain judgments made on that, which I wasn’t expecting. I think the harshest thing we do, as men or women, is presume to know someone’s life and the rationale for their decisions. I was quite surprised by the “ambitious” label that got put to that choice. That decision was, in fact, one I had to make—I went from major breadwinner to sole breadwinner in my household at that time. And you know, 19 years later, as my daughter’s off in university, it all worked out OK. But it was interesting for me to see how quickly the narrative changed when I talked publicly about my decision. Criticisms about whether you have a child, don’t have a child, stay home, don’t stay home—they’re your life choices, and people need to respect that.

As one of the handful of women in prominent positions in the Canadian business landscape, do you get tired of representing women?

I’m very conscious of the fact that representing women is important. What I worry about is the box people put me in. When I’m on a panel or in an event, have I checked off a certain box because I’m the woman? But I’m also hoping that it at least means my voice is being heard and maybe it encourages others to speak up. There’s a catch-22 around being a woman leader. But I think it’s important to let that be the thing that lifts you up and creates opportunity.

What about workplaces? What should they be doing to make sure women get their turn to lead?

Initiatives in workplaces are important. When I was at CBC, I made sure the diversity team reported directly to my office. Despite advancements, diversity is a muscle that needs constant flexing.

Do you believe in quotas or targets?

I definitely believe in benchmarking and seeing where the numbers are going. I don’t believe in saying, “We need to reach that quota by this year.” But I think watching how the trend is going up or down within the company is incredibly important.

Twitter has a workplace SWAT team—which stands for Super Women at Twitter. What do they do?

It’s a self-formed group of women who see the opportunities and benefits of working together. Currently, the SWAT team is doing a great job at passing around open opportunities within the company to remind people, “Hey, if you have anybody or know anybody to fill this role, that would be great.” There’s also a group within the company called Blackbirds, which is the black Twitter employee group. There’s an LGBT group too. I think these are ways to remind ourselves that when people come to work, they’re still individuals that represent a certain lifestyle or person. You don’t have to give that up when you come through the door.

Were you surprised by the media scrutiny when you left the CBC?

I thought I’d go off to this nice new job at Twitter and the big question would be, “Who’s next at CBC?” because it’s an institution that’s obviously bigger than any one person. I was shocked to see the questions they asked were incredibly personal. It was like, “Is she either the genius who saw the future or is she the idiot who just gave up the biggest job ever?” I happen to think I’m somewhere in between.

So what was it specifically that spoke to you about Twitter?

I like the openness of the platform as a communication tool—it isn’t one-way, whereas broadcasting still largely is. I think Twitter provides a great partnership platform for traditional media to speak in a new space. And there was the comfort of knowing we’re actually there to help everybody. We’re helping not just newspapers, magazines and television networks but also bloggers, people off the street who take a shot and tweet it.

You’ve said one of your greatest strengths is knowing how to find broader audiences, something you did successfully at CBC with shows like Battle of the Blades. What’s the secret?

I think it’s easy to put yourself first, when you’re sitting in an office, concerned about the day-to-day operations of an organization. Particularly in the media space, you have to be careful to make sure you’re not just speaking to people like you. You have to take yourself out of your building, your world, and look at who else is out there. Maybe my thinking comes from the fact I didn’t go to a tony private school; my family isn’t connected to anybody. We were immigrants who came to Canada.

I started my career with a $16,000 a year receptionist job. When you come from average, you realize how important it is to listen to others. When I was at Alliance Atlantis, I took my staff on the GO train one day to remind ourselves what life is like when you’re not in downtown Toronto. We went west to the Bronte area, and east to the Ajax side as well. And we could see what people appreciated there and see that they do pretty fine with Walmart drapes. It’s so important to get close to an audience and to understand what’s important to them, so you can speak to them with their value system.

How are you aiming to find a broader audience with Twitter, which is struggling these days to maintain its user numbers, never mind grow?

I think we’ve done an incredible job of partnering with a lot of media outlets and journalists. I think the next phase is finding the individual. We’ve seen the rise of the individual, whether it’s through Ferguson or the Arab Spring—you can see the opportunities for individuals to be heard in a way they hadn’t before.

I read that you were once told a surprising revelation by a fortune teller. What did they tell you?

It’s true. I was in Hong Kong at an industry party, and on every floor they had a different form of fortune teller. So I had my palm read, and he said, “You will be prime minister of your country some day.”

Have you ruled that out?

Yeah, totally. I think I have more opportunities for influence on this side.