'Katie's Boat Rarely Rocks': Meet The Most Influential Woman In Canadian Politics

Katie Telford's rise has been largely under the radar. Now, as chief of staff to Prime Minister Justin Trudeau, she advises him on just about everything — from the economy to Ivanka Trump — and she's determined to level the playing field for women in Ottawa.
By Sarah Boesveld
Katie Telford, chief of staff to Justin Trudeau All photos by Adam Scotti (PMO PHOTO)

It's noon on a Friday and one of the grandest meeting rooms in the Prime Minister’s Office — all lush red carpets, glossy wood-panelled walls and vaulted ceilings — is filling with women staffers. They clutch Tupperware containers carrying leftovers for lunch and search for their names on white place cards set on an oval, United Nations–style table typically occupied by senior officials. It’s a PA day at school, so one woman has her spunky five-year-old daughter perched on her lap, working on a colouring project.

Fifteen minutes later, they pipe down as the most influential woman in Canadian politics walks into the room, a five-year-old of her own trailing behind. She apologizes for keeping them waiting before convening the third women’s lunch-and-learn meeting of the PMO — a ritual of segregation, sure, but a cathartic one in this male-dominated high level of Canadian politics.

To the people gathered around that table, Katie Telford needs no introduction. In Canada’s corridors of power, she’s one of Prime Minister Justin Trudeau’s closest advisors, a masterful political strategist and a key driver behind the Liberals’ push for gender equality. But since there are interns present today, she takes her turn as they go around the table. “I’m Katie, I’m chief of staff. We have one exception to the no-boys rule today,” she says, looking toward her lightly freckled son, George, who smiles back up at her. “I decided if [the] is under a certain age, it is okay to have him.”

In most government meetings, Telford tallies in her notebook how many women are in the room, compared to men. It’s often just two: Telford herself and the PMO’s director of communications, Kate Purchase. But this isn’t a typical day: These 36 women were invited here by Telford to talk casually about being a woman in politics — and the topics cover everything from sexism to perceptions of feminism to work-life “mix” over “balance.”


She hopes to ignite a spark in her staff — to make them “comfortable talking to each other about this kind of stuff,” she says after the lunch, seated comfortably on a green couch in her office. “At least, that’s part of my goal.”

In addition to sitting in on cabinet and caucus meetings, managing senior staff, weighing in on matters of national security, and advising on nearly every decision Trudeau makes, Telford is also known for having an impeccable Spidey sense and not suffering fools. Between her many confidential meetings in a day, she tries to set a family-friendly culture (“It is everyone’s mission that I get home [to] Harry Potter with George,” she says, adding that having kids run around the halls, on occasion, is akin to “pet therapy.”) And she’s determined to make good on one particular promise from the Liberals’ 2015 election campaign platform: to make Ottawa a place where the numbers of men and women around any given table are equal. A place where someone like her wouldn’t keep a tally in a notebook.

Despite a gushing story on the cover of Rolling Stone magazine positioning Trudeau as “the free world’s best hope,” there’s no denying that women in Canada still face an uphill battle in politics and women’s issues can still take a back seat where policy is concerned. The Liberals’ plan for electoral reform, which some have said would help even the playing field for women running for office, has been abandoned. MPs have talked openly about the sexism they face in the House of Commons, and politicians from across the country are concerned the advancement of women in politics is being undermined by the bullying they experience on social media. Sure, gender analysis played a part in the 2017 federal budget (so that the impact of policy decisions on women was specifically taken into account), but there is skepticism about how effective a new child care agreement with the provinces will be, and women — Indigenous women, immigrants and refugees in particular — are still disproportionately affected by poverty. The vaunted and long-awaited inquiry into missing and murdered Indigenous women has been mired in challenges and conflict. And the government’s move to extend maternity leave to 18 months, without expanding employment insurance benefits, was criticized as being helpful only to those who can afford to go without extra financial assistance.

Katie Telford, chief of staff to Prime Minister Justin Trudeau Telford is sometimes frustrated with the slow pace of change in government. 'What we're trying to do is not easy, and yet there are a lot of people who expect results yesterday and, you know, for good reason.'

These are problems the Liberals say they are working to fix, through policy decisions they hope will result in a massive culture shift. And while Telford is proud of the progress made so far, how the party will deliver on its ambitious promises is what keeps her and her team up at night.


To make this lunch meeting, she took a red-eye from Vancouver, after having attended a soiree with billionaire philanthropists Bill and Melinda Gates in Seattle. But if she’s feeling sleepy, it doesn’t show. She leans back in her chair, pulls her hair up into a ponytail and down again, focusing intensely on the women’s stories — about men who gripe about women snagging federal appointments because of “optics” or women being told by male co-workers to “go for wine and sort out” a conflict. She shares her own stories too — about how the prime minister is always quick to introduce her as his colleague on foreign visits because she’s so often mistaken for his wife. At one point, Telford turns to George and wryly says, “You’re going to be a raging feminist, aren’t you?”

Raging, however, is the opposite of Telford’s style, according to former and current colleagues, as well as those close to her. Her résumé may boast one barrier-busting achievement after the next, but her rise has been understated, playing out mostly behind the scenes.

Trudeau’s nonchalant “Because it’s 2015” shoulder shrug became the international symbol of our country’s #feminist cred. But what the world didn’t see was Telford and her team working tirelessly to recruit women candidates, since 2013, with the goal of eventually building a gender-balanced cabinet. When Finance Minister Bill Morneau spoke about how the 2017 budget would impact women specifically, it was because months earlier, Telford raised her hand in a finance meeting to ask if anyone had considered adding gender analysis as part of the process. (No one had.)


These were both tone-setting moves made while the Trudeau honeymoon was hot. Now, halfway through the Liberals’ rule, Trudeau’s critics, citing inaction on Indigenous issues, pay equity and violence against women, are lobbing accusations that his commitment to women’s issues and equality is all hashtags and photo ops, and little substance.

It’s a criticism that irritates Telford: For every quibble, she says, there is a success that goes uncelebrated. But it doesn’t throw her off course — indeed, those who’ve worked with Telford in the Ontario legislature or on the campaign trail say nothing flusters the 38-year-old. She is determined to move the dial on gender representation in Ottawa. And she knows she has a unique and historic chance to make it happen: “I have to be the woman in the room who says, ‘Where are all the other women in the room, and how do I get them here?’”

Much like her rise in politics, the real work of this shift will happen behind the scenes — without a ton of fanfare, without any prom night photobombs or selfies — and it will be fuelled by connections and conversations, like the ones she’s having today.

Student politics, the debate club and Bob Rae's cockapoo, Cindy

Back in the early ’90s, when then-Ontario NDP premier Bob Rae had an important guest over for dinner, he would sometimes ask his young neighbour, Katie Telford, to watch his dog, a cockapoo named Cindy. Telford, the daughter of Peter and Phyllis, both public servants (Phyllis became a stay-at-home mom after Telford was born), would sit on her front stoop in the upper-middle-class Toronto neighbourhood of High Park and watch the comings and goings that made up the life of their influential neighbour. Occasionally, the procession of “fancy” visitors was replaced by rowdy protesters, and at least once a brick was thrown at the house.

Telford credits her politically powerful neighbour, the man who would also drive in the carpool for orchestra practice (she played violin), with inspiring her to get into politics, “whatever the party.” In grade 7, she joined the page program in the Ontario legislature, adding it to an already packed schedule of extra-curriculars at which she excelled: competitive swimming, cross-country skiing and public speaking at local Legion halls.

CHE04_web_teleford03 Telford joined the page program at the Ontario legislature in grade 7, inspired by her neighbour, then-premier Bob Rae.

Telford was an especially good orator — a skill that came in handy when she was elected student premier of Ontario in grade 12, a role that saw her travel to high schools across the province to deliver motivational speeches.

“Katie was always a bit of a leader in her class — not Ms. Popular, more like Ms. Respected,” says her younger brother, Fraser. She was a super overachiever who still got invited to parties, he said; a Dirty Dancing fan with a perm, voted “Most Likely to Become A Rocket Scientist” in her Grade 10 school yearbook.

She went on to study political science and history at the University of Ottawa and found a natural home for her public speaking chops in the nerdy world of university debating — a sphere also occupied by Gerald Butts, now principal secretary to the PM and her daily co-conspirator, and even Trudeau (though she and Trudeau never crossed paths there). She also worked as a page in the House of Commons. Around the same time, she met her future husband, Rob Silver, at a tournament at Western University, where he was studying law. “She was a lot of fun,” Silver says.

“Did I think she was going to be the chief of staff to the prime minister of Canada? No. But you could tell she was destined for big things, even then.”

Katie Telford In most government meetings, Telford tallies in her notebook how many women are in the room, compared to me.

Partisan politics, a big promotion and the Power Chicks


After graduation in 2001, Telford returned to Toronto, looking for a job. She made her first dip into partisan politics working on Bob Hunter’s by-election campaign for a Liberal seat in the Ontario legislature; soon she met Liberal MPP Gerard Kennedy, a young, ambitious political hotshot who represented her home riding of Parkdale–High Park. September 11, 2001, a day that shut down pretty much every workplace in the Western world, was 23-year-old Telford’s first day working for Kennedy as a legislative assistant at Queen’s Park — and her life as a trusted behind-the-scenes Liberal began. “Katie has this funny thing of not being noticed, and then when you do notice her, you get her full force,” Kennedy says, calling it a “skill set” that he used to his advantage.

At Queen’s Park, Telford toiled in Opposition, where Kennedy first served as education critic, and helped craft the Liberals’ education platform for the 2003 campaign — presented as part of a last-minute bid to lift leader Dalton McGuinty in the polls. The focus proved so successful, McGuinty positioned himself as the “education premier” and Kennedy was named minister of the file. Telford had her sights set on a promotion to executive assistant, but Kennedy didn’t want to rush it. She wasn’t having that at all. “There was a day, a year in, that she just announced, ‘You will give me this promotion,’” Kennedy says, admitting that “by then, it was overdue.”

Six months later, the tables had turned and it was Kennedy who spent weeks agitating in the premier’s office for a promotion for Telford — to make her his chief of staff, one of the youngest in the history of Ontario politics. With help from Butts, who was working as the premier’s policy advisor, McGuinty was persuaded she should have the role, and she took the job just days before her 26th birthday.


It was a huge achievement, but one that, she quickly discovered, afforded her zero luxuries. One of Telford’s greatest tests came when elementary school teachers were looking for a better deal with the province. She spent day and night for months negotiating in a room full of grizzled union reps. “On that first day, there was this hard-core negotiator who came up to me at break and said, ‘I looked you up — where were you before this?’” Telford says. She remembers praying that they wouldn’t Google her to find only her debating stats, and thinking, “There’s no way they’re going to take me seriously, so I’ve got to just impress them with my here and now.” A deal was reached with no strikes and no lockouts — a first-ever four-year agreement that introduced new negotiation frameworks for Ontario and guaranteed a minimum amount of teacher prep time across the province.

It was also in this role, having endured once being literally patted on the head in her time at Queen’s Park (she’s five feet tall), that Telford began to understand what it was going to feel like to be the only woman in the room. “In the sphere I know . . . you have to find a different way to have your voice heard or think a little more three-dimensionally about how to make it happen.” She was adopted into a small clique of the few other female chiefs of staff for Ontario ministers who called themselves the “Power Chicks” (remember, it was the early 2000s). When Telford became chief of staff to the prime minister, they gave her a pen engraved with their now somewhat cheesy group name — it sits in a case on her desk in the PMO.

The Power Chicks offered a wealth of advice, but little could prepare her for the sexism she faced when Kennedy decided to throw his hat in the ring for the federal Liberal leadership and asked her to run his campaign. Her friend and Kennedy’s communications director at the time, Amanda Alvaro, recalls major Kennedy backers in Ottawa threatening to walk away from his bid if a young, “unproven” woman was running the show. It upset Telford, Alvaro says, but it didn’t knock her off course. “Katie’s boat rarely rocks.”

When echoes of the same attitude returned during Trudeau’s election campaign, “she was prepared for it,” Alvaro says. “She was like, ‘Been there, done that.’”

Her first defeat, a baby, and "just Justin"

Back when Telford was working on Kennedy’s leadership bid in 2006, a guy who was then “just Justin” offered to lend his support. Her strategy had been to sign up as many young people as possible, Kennedy says, and Trudeau’s youthful energy aligned with that goal. Butts and Telford — who by then had established a close working relationship at Queen’s Park — set up a meeting between Trudeau and Kennedy to work out the details. Then Trudeau asked to meet with Telford ahead of the leadership convention, where he intended to pledge his support for Kennedy. They sat down in a coffee shop near Ryerson University, and clicked right away — talking about everything from world events to the state of the country to the leadership race itself. “We just kind of both dug in,” Telford says, looking back on the meeting. As he was about to leave, Trudeau turned on his heel and said, “I wasn’t quite what you expected, was I?” But Telford says that, at the time, she hadn’t given much thought to what she should expect from him.


At the Montreal convention, however, as she watched him work the room, it became clear that Trudeau’s magnetism would make him the Liberals’ next political powerhouse. “The connection between [Trudeau], many of whom weren’t sure what the future of the party was, most of whom had never met him before . . . was something I had not seen,” Telford says.

That enthusiasm stayed with Telford long after Kennedy lost the leadership and she ended up working in the office of the new leader, Stéphane Dion. She rose in the ranks to deputy chief of staff but left after two years. “It was a pretty ugly time in the party,” she says. “That was hard.”

She moved on to work at StrategyCorp, a political strategy firm in Toronto, and started a family. George, born in June of 2011, was barely a year old when she, Butts and Trudeau met at Barootes restaurant on King Street West in Toronto to hash out what was becoming a distinct possibility: Trudeau’s own run at the leadership. Telford and Trudeau had kept in touch since the convention — she advised him from the sidelines on his first Liberal nomination (which he won) and his run to represent the Quebec riding of Papineau (which he also won, by a landslide). A few months later, during a breakfast meeting, Telford got the official ask: Would she run his leadership campaign?

CHE04_web_teleford05 During the 2015 election campaign, Trudeau told supporters that he chose Telford as a leader of his team specifically because she wasn’t a member of the ‘old boys club.’

It was a job “rarely done by women in politics, especially women with young families,” writes veteran political reporter Susan Delacourt in her 2013 e-book on Trudeau’s political rise. Again, Telford was undaunted. At one of Trudeau’s very early planning retreats at Mont-Tremblant in Quebec, before he made his official announcement, Telford brought George along. “It was kind of like, ‘If you’re gonna want me, you’re gonna want me and my kid,’” she says. While that might have been a non-starter in political circles a decade ago, there wasn’t a conference call during the entire leadership campaign, Butts says, when somebody’s child wasn’t screaming in the background.


Not everything went smoothly early in the campaign. Some attempts to draw more women into the fold, including the notorious “Ladies’ Night” fundraiser in 2013, which invited women to eat candy, drink pinot grigio “and (really) get to know” Trudeau, were criticized both within the party and externally for being patronizing. (Telford stands by the move, saying the only thing she wishes she'd done differently is “double down sooner” on the idea behind the event, noting that it drew in more than 100 women who had never been active in politics before.)

As the 2015 election neared, Silver feared once again that Telford would be judged “not old enough, not male enough, not Ottawa enough” and be turfed in favour of the old guard if Trudeau ever sunk in the polls. That low moment came in the spring of 2015, and rumours swirled that she and Butts were on the way out.

But Trudeau had earlier told supporters on the trail that he chose Telford expressly because she was not a member of the old boys’ club. And despite that drop in the polls, the Trudeau team was already seeing stellar on-the-ground results from a strategy Telford had picked up during her time with Gerard Kennedy: a passion for numbers. From her former boss, she learned to track data obsessively, understanding that for her, numbers would come in handy in more ways than one. “One of the reasons I like numbers, besides the fact that I’m a naturally evidence-based person, is gender-related,” she says. “It’s harder to fight with me when I have a number.”


Telford tracked the numbers in each riding daily and let Trudeau do his selfie thing on the campaign trail. Riding a youthful wave of enthusiasm, the Liberals rose from third-party position to first and then, partly lifted by the votes of millennials and young women, secured a majority. The roots of that success start with Telford, says Conservative campaign manager Jenni Byrne, her direct rival in 2015. “For the first time in the last several elections, the Liberals actually had a decent ground game,” she says. “She should be credited with influencing the cultural change that made it happen.”

The U.S. election, Billy Bush, and Ivanka Trump

On the night of November 8, 2016, Telford and 20 or so others from Trudeau’s inner circle huddled in front of a TV at the prime minister’s home to watch the results of the U.S. presidential election spill in. Early on, when it looked like Hillary Clinton would be named the next president, data-loving Telford wasn’t going to call it either way. When it became apparent that Donald Trump would win, the room quieted. A reality TV magnate who was caught on tape telling Access Hollywood host Billy Bush he liked to grab women “by the pussy” had now become their most important relationship to navigate. Telford just said, “Well, we’d better get a good night’s sleep.” Her thoughts immediately turned to how they were going to work with a Trump administration.

She had seen Ivanka Trump speak at the Fortune Most Powerful Women Summit in California the month prior. She knew of the American businesswoman and former model’s desire to be seen as an advocate for feminism. And she nearly missed her plane home in order to witness firsthand how Ivanka would handle questions about the alleged sexual indiscretions that dogged her father’s campaign. “She was impressive — she handled it with a lot of poise and grace,” Telford says.

So when she started thinking about the framework for Trudeau’s first face-to-face meeting with the new U.S. president, she saw a path to a smooth start — and it began with Ivanka.

Her pitch: Trudeau would make his first official visit to meet the U.S. president and push for gender equality while speaking Trump’s language — business. The Canada-United States Council for Advancement of Women Entrepreneurs and Business Leaders was born and approved by senior Trump advisor (and Ivanka’s husband) Jared Kushner, as well as Trump’s assistant and senior counsellor for economic initiatives at the time, Dina Powell.


It was a huge gamble. Helping to improve Trump’s brand could have been extremely damaging to Trudeau’s #feminist bonafides. But they pulled it off without much of a ripple, and with both parties pleased: Trudeau got to make good on a promise to push the advancement of women in business, Trump backed the idea and Ivanka — then acting as a kind of quasi First Lady — had a seat at the table. “One of the most important jobs [we] managing the relationship with the White House,” Butts says. That first meeting “just would not have happened the way it happened without Katie.”

Since then, Trudeau has mostly played coy when it comes to the U.S. president, finding passive ways to reassert his feminist credentials without directly criticizing Trump. He popped up at the Women in the World summit in New York City in April, for instance, to talk about why he is staunchly pro-choice, and about Canada’s $650-million pledge toward improving reproductive health in the developing world. (He neglected to mention that it was Trump’s reinstatement of the global gag order that led to the need for that funding boost.) The comfortable distance he’s been able to maintain, however, got a lot closer when Rolling Stone effectively used the Trudeau interview to troll Trump, who is notoriously thin-skinned, asking the universe, “Why can’t he be our president?” (Butts insists the story doesn’t pose any kind of threat to the Trump-Trudeau relationship: “If the prime minister has standing and stature in the U.S., and other important markets to the U.S., that’s always positive.”)

CHE04_web_teleford02 When Telford first met with Trudeau at a coffee shop, they clicked right away. ‘We both just kind of dug in,’ Telford says. Six years later, he asked her to run his leadership campaign.

The Telford effect: Young faces, revamped parties, and a new political landscape in Canada

Now, nearing the halfway point of the Liberals’ majority government, their campaign tag line “Real change” is being challenged more and more. While Canada’s economy is doing well at the moment, experts worry the relatively quick growth won’t last. Trudeau has also been criticized for not doing enough to protect the environment, and the gender-balanced cabinet has come under scrutiny, with critics pointing out the flat-footedness of some of the more inexperienced women cabinet ministers. As Byrne puts it, “The worst thing you can do for someone, a man or woman, is over-promote them from what their ability is. You’re making them tread water and, potentially, they’ll never get their sea legs.”


Still, there’s no denying that the political landscape in Canada has changed in the past two years. The 2019 federal election will see Trudeau face off against new Conservative Party leader Andrew Scheer, who, at 38, is seven years younger than Trudeau. The NDP elects a new leader in October, and all eyes are on stylish 38-year-old lawyer Jagmeet Singh.

But the question still lingers: Is this more youthful shift, with a focus on gender equity, making life better for Canadians, and women in particular?

Telford has her own frustrations with the slow pace of change in the federal government: “What we’re trying to do is not easy, and yet there are a lot of people who expect results yesterday and, you know, for good reason.” And then there are the pains that come with identifying a government as having, and benefitting from, a feminist identity — in Trudeau’s case, one that’s been criticized as surface level, white, privileged and business-focused.


“Whether [Trudeau] one kind of feminism and whether he’s a real feminist or a fake feminist — that all drives me crazy,” says Telford. There are good, substantial policy gains that have been implemented in the past two years, she says, including Ottawa’s intervention to help Prince Edward Islanders get long-denied access to abortion services (“How many people remember that when they talk about his latest feminist speech?” she says). On the topic of the government’s perspective being too white and too elite, however, Telford says she is listening. “I like to think we welcome and encourage not just pushback but pushing us forward. There is no denying there is more work to do.” She’s tracking numbers on ethnic diversity in government, another major challenge for the administration.

Her friends and family have noticed a change in her — a new fire that’s been lit. “It’s hard for me to describe the transformation, but there has been one,” says Alvaro. “I think she’s finally proud of what she’s accomplished. She’s comfortable in her own skin.”

Asked what’s next for her (besides trying to get the Liberals re-elected in 2019), she takes a thoughtful pause — not an uncommon thing in a conversation with Telford. “There are lots and lots of moving pieces in my head, definitely more than I’ve ever experienced,” she says. Within the past year, Telford spoke at the Fortune Most Powerful Women Next Gen summit and sold out a Lean In Canada talk in Toronto. But, perhaps unsurprisingly, she returns to the opportunity her present role affords: to advance the cause of women and to make Canada, broadly, a more equitable country. “It’s such an opportunity in such a finite amount of time.”

And as if on cue, a pint-sized time-keeper is deployed to inform Telford that our time is up. “Mom! You’re late for your next meeting,” George says, poking his head through the doorway. “Well played,” Telford says to her executive assistant, who is standing just behind George, sporting a wry smile. “Well played.”


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