The 10 women around the table at The Carbon Bar, a hip cocktail and barbecue spot on Queen Street East in Toronto, were in a celebratory mood. It was Friday night just a couple of weeks before Christmas, and the drinks and conversation were flowing.
For the first time in months, the close-knit group, who have known each other for years and whose careers have now taken them all over the world – one is a senior political assistant, one is in public relations; others are in tech, or are entrepreneurs – were all together. The ritual mattered to them: One woman had flown in from California, another from New York.
For them, 2015 had been a stellar year. There was a new baby to celebrate. A couple of them had new jobs. Another had just started a business.
But the main reason for the gathering was to fete one woman, in particular: Katie Telford. The political strategist had been the co-chair of Justin Trudeau's election campaign, orchestrating a stunning victory that took the Liberal Party to its first government in more than 10 years.
Now, at 37, Ms. Telford, is one of the most influential people in Canada.
As the chief of staff to the Prime Minister, she is also only the second woman ever – Jodi White had the job for a few months in 1993, under Kim Campbell – to serve in that position.
"This is someone who knew exactly what she wanted and, despite the naysayers, was going to get it," says Amanda Alvaro, a public-relations specialist, and one of Ms. Telford's best friends.
That night, Ms. Telford regaled the group with tales from the campaign and the whirlwind aftermath. She recalled the ceremony at Rideau Hall in early November when Mr. Trudeau and his cabinet were sworn in, and the magnitude of what she and the Liberal team had achieved finally washed over her.
Then she described meeting U.S. President Barack Obama. After months of working at the Liberal headquarters in a downtown Ottawa office complex, Ms. Telford was face to face with the most important man in the world. He looked at her specifically, she told her friends, and acknowledged the tremendous campaign she had run.
The question is: Now that she's helped get Mr. Trudeau into office, how will she manage the ambitious agenda and inevitable pitfalls that are ahead?
BEFORE THE RISE, A FEW DISASTERS
Ms. Telford does not immediately stand out. She is exactly five feet tall; her hair is often pulled back in a ponytail. She wears little makeup and her clothes are businesslike. She is the epitome of the old-style political aide: shunning the spotlight, getting the work done. She would not be interviewed for this story.
Everyone who did talk to The Globe, however, noted her intelligence, quiet resolve and steeliness. They also talked about how she is often underrated by those who cross her path. "She has been beating bias about her age and gender for a long time," says her colleague Gerald Butts, Mr. Trudeau's principal secretary.
Adds Ms. Alvaro: "She is small in stature and not aggressive. People, at first blush, underestimate her, and that has worked to her advantage." She is known for two attributes, too, that can be rare in politics: She is calm, and she is not mean.
Politics is a high-pressure business, and comes with a lot of potential for catastrophe – and, as a result, bad behaviour. Former prime minister Paul Martin, for example, was legendary for his eruptions and for berating his staff. Ms. Telford is not like that, say those who know her. With her, there is no drama.
"There was no backbiting," says David MacNaughton, a senior Liberal strategist and friend of Ms. Telford, about the recent campaign.
"Many of the former [Liberal politicians and officials] who weren't so plugged into the party any more were shooting at Katie and shooting at Gerald … but there was never any crack in that."
Ms. Telford never let such criticism affect her plan, or her relationships with her team. Ignoring the noise, she focused on strategy.
"I have been in campaigns where it's just awful," added Mr. MacNaughton. "Whether you win or whether you lose, it's people jockeying for position, and playing politics. There was none of that. It just didn't happen, even when things weren't looking great."
Now that things are looking great, no one will speak on the record about Ms. Telford's weaknesses or vulnerabilities. This is what happens when it's going well for a government: People close ranks. It's when everything goes off the rails that the knives come out.
Certainly Ms. Telford is by no means perfect. Her meteoric rise in the party came by way of several disastrous campaigns: She managed former Ontario education minister Gerard Kennedy's losing federal Liberal leadership bid in 2006, and was involved in former federal Liberal leader Stéphane Dion's calamitous 2008 federal election campaign.
"She's had the shit kicked out of her a lot of times," says a veteran Liberal organizer who played a senior role in Mr. Trudeau's 2015 campaign and asked not to be identified.
He added that – both when Mr. Trudeau brought her in to spearhead his 2012-13 run for leader, and when he made her a key member of his team for the federal campaign – there were questions among some older party members and strategists about what she could contribute.
Such critics proved no match for the results Ms. Telford was eventually able to deliver. Clearly she had learned from her earlier failures.
HAPPY TO EXPLOIT THE WEAKNESS OF FOES
Very early in the 2015 campaign, Ms. Telford had a hunch that made no sense to the Liberal number crunchers.
Peter MacKay, who a dozen years earlier had led the merger of the old Progressive Conservative Party with Stephen Harper's Canadian Alliance, had decided not to run for re-election in the Tory stronghold of Central Nova. But while the riding was officially open, the idea of a Liberal taking it was, so went the conventional wisdom, preposterous.
Ms. Telford saw it differently. With the Tories losing their anchor in the region, she recognized a weakness the Liberals could exploit: Tories in Nova Scotia saw Stephen Harper as the guy who had done in their native son – and the Conservatives' nomination of a candidate who had worked closely with Mr. Harper as salt in the wound.
Ms. Telford insisted more resources be sent into the province, and even dispatched Mr. Trudeau there to campaign. She never flinched. "Leadership is really that time when you stand against the tide," says a senior campaign official. "There was no data to support those decisions. Katie is very-data driven. [But] this was a gut decision and she turned out to be right."
The Liberals won Central Nova. Not to mention the rest of Nova Scotia, and every riding in the three other Atlantic provinces, too.
FROM EARLY ON, A POLITICAL BENT
Ms. Telford and her brother, Fraser, grew up in High Park, a well-to-do neighbourhood in Toronto's west end. Their parents, Peter and Phyllis, were provincial civil servants, and imbued their daughter with a passion for public service. Combined with her natural ambition – she was a competitive cross-country skier and swimmer, and won numerous public-speaking competitions – that passion attracted her to politics and government at an early age.
As a young teen, Ms. Telford was a page in the Ontario Legislature. In high school, she was elected by delegates from across the province as Ontario student premier. During her first year at the University of Ottawa, where she would study history and political science, she was a page in the House of Commons.
Queen's Park plays a central role in Ms. Telford's political journey. The Telfords lived in the riding of York South, where Gerard Kennedy, who would later become education minister in the Liberal government of Dalton McGuinty, first ran in a 1996 by-election (after Bob Rae, the former Ontario NDP premier, stepped down as leader and resigned the seat).
As he looked through lists of volunteers in the riding, Mr. Kennedy kept running across Katie Telford's name on youth lists – and he was looking for young people to join his campaign. Eventually he succeeded and she came to work for him at Queen's Park.
In the meantime, Ms. Telford had met her husband, Rob Silver, in university debating circles. They are currently planning a move, along with their four-year-old son, George, back to Ottawa.
DOUBTS, AND UNDERESTIMATIONS
At Queen's Park, with the Liberals in opposition, Ms. Telford was at first Mr. Kennedy's general assistant. But she eventually worked her way up to chief of staff.
In the 2003 Ontario election campaign, Mr. McGuinty, then the opposition leader, put a firm emphasis on education. With four days' notice, Ms. Telford was thrown into the Grit war room and managed that part of the platform during the successful campaign.
Still, once Mr. McGuinty took office, the premier's most senior people, who have a say in the hiring of ministers' staffs, didn't want her as Mr. Kennedy's chief of staff. It took six months for Mr. Kennedy (with help from Mr. Butts, then working in the premier's office) to convince the powers that be that she should get that role.
Over time, Mr. Kennedy, Ms. Telford and others in his office created a provincial template that the teachers' unions had to work within. And yet, despite allowing that strategy to proceed, the aides in Mr. McGuinty's office had little faith that it would work. Recalls Mr. Kennedy: "The only contingency the premier's office had was for failure."
As negotiations later unfolded, Ms. Telford would conduct initial discussions with the teachers, and then Mr. Kennedy would come in and try to close the deal. "When Katie walked into the room, they assumed she was the assistant to the assistant," says Mr. Kennedy. But the strategy worked. What followed was labour peace: 122 contracts landed within six weeks, and not one day was lost to strikes or lockouts in the next four years.
CIGARETTES AND TRUST
It was at Queen's Park, too, that Ms. Telford cemented relationships with key political players, especially Mr. Butts, who went on to become Mr. McGuinty's principal secretary, and who years later would be her main colleague-in-arms on the Trudeau campaign.
For almost two hours one spring day in 2006, Ms. Telford and Mr. Butts sat on a park bench on the northeast side of the Ontario legislature, chain-smoking, in intense conversation. They were trying to work out an exit strategy for Mr. Kennedy, who had decided to step down from his post as education minister and resign from provincial politics, in order to seek an even bigger prize – leadership of the federal Liberals.
Mr. Kennedy and Mr. McGuinty had been intense rivals for the Liberal leadership. In fact, at the 1996 provincial convention, Mr. Kennedy was considered the front-runner, winning the first four ballots, only to be defeated by Mr. McGuinty on the fifth. A decade later, they still had loyal supporters in each of their camps, and distrust remained among some of them.
In politics, exits are never easy and can reflect badly, if not handled properly, on the leader, the party and the government. This one was especially tricky, given that education was Mr. McGuinty's top priority and that his education minister had once been a fierce opponent. Ms. Telford and Mr. Butts were instructed to make it seamless.
During their conversation, they committed to making sure no one "screwed each other," according to someone close to the negotiations, who asked not to be named. There would be no dark whispers, no backstabbing, and God forbid, no leaks to the media until both sides were ready to make an official announcement.
There were no raised voices or emotional outbursts that spring day on the park bench – just a lot of cigarettes and a lot of trust. Ms. Telford and Mr. Butts made it work – and, soon after, Mr. Kennedy made his announcement. At the tender age of 27, this is how Ms. Telford came to manage her first big leadership campaign.
AT A CRITICAL MOMENT, WEAKNESS
The campaign would be a failure.
Mr. Kennedy came into the race with a lot of promise – and as fresh-faced, youthful and energetic, compared to front-runners Michael Ignatieff and Bob Rae.
But his campaign failed to deliver – he was fourth on the first ballot, losing by just two votes, and dropped out after the second ballot to support Stéphane Dion, who went on to win. The loss exposed one of Ms. Telford's weaknesses, according to a senior Liberal insider, who said that her biggest challenge was dealing with the Kennedy campaign volunteers: including them in decision-making, for example, assigning them clear roles, and distinguishing between those who really perform and those "trying to get ahead for position."
The Kennedy team failed to do this. As campaign manager, Ms. Telford was responsible. "I am sure Katie would say this was a hard lesson learned," says the source.
The expectation had been that Mr. Kennedy could come third on the first ballot, which would set him up well for the future ones. But he fell short. His lack of momentum led to his decision to drop out of the race.
THE DION DISASTER
That's how Ms. Telford came to Parliament Hill: Mr. Kennedy had supported Mr. Dion, and the new leader looked to his opponents' teams when recruiting staff members, to ensure that he had good representation from the other leadership candidates.
Ms. Telford joined Mr. Dion's office, at first to work on policy. Given her experience at Queen's Park, it wasn't long before she became his deputy chief – and soon found herself involved in another disastrous campaign – that of Mr. Dion to become Canada's prime minister.
Says one Ottawa insider: "They screwed up in so many different ways."
First, there was the delay in finding a campaign plane for the 2008 election. When they finally did, it was a 30-year-old gas-guzzling Boeing 737 owned by Air Inuit. It leaked oil – and became a metaphor for the poorly run Liberal campaign.
Then there was the doomed "green shift" carbon-tax policy – Mr. Dion's vision for addressing climate change. It was a crucial part of his platform, and one that he could never easily explain to voters. Ms. Telford was travelling with the leader on the plane, as a close adviser, throughout the election.
In the end, the Liberals lost 18 seats in that election, reducing their presence in the Commons to 77 MPs, and the Harper Tories won their second minority government.
But if the election was disappointing, what came next was simply embarrassing.
Being in opposition in a minority parliament is challenging: Every week, you're trying to decide if this is the time to bring down the government. Mr. Dion and his team were faced with that decision during the 2008-09 confidence crisis – and they bungled his response to Mr. Harper's decision to prorogue the House of Commons to save his government.
When the Liberals and NDP announced they would form a coalition government backed by the Bloc Québécois, Ms. Telford was among those at the table representing the Dion team. She was also there for Mr. Dion's botched videotaped national address, in which the camera slowly tilted downward as he delivered his statement.
Shortly after that, Mr. Dion was replaced by Mr. Ignatieff. And Ms. Telford headed back to Toronto, and to the lobbying firm StrategyCorp., where David MacNaughton, who would later work with her on Trudeau's 2015 campaign, is chairman.
Liberals who worked with Ms. Telford on Mr. Trudeau's federal campaign describe her as methodical and data-driven, analyzing overnight polling numbers and sending early-morning e-mails to campaign team members questioning, for example, a leak to a reporter in a news story. She also provided the provincial teams with specific time lines and her precise expectations for meeting them. And long before the writ was dropped, she had also pushed the provincial teams hard to find women candidates.
In fact, much of the campaign's success happened because of the detailed groundwork laid by Ms. Telford and Mr. Butts, which began immediately after Mr. Trudeau took over the party's reins. The two often travelled to Washington, meeting with former Obama aides Jen Dillon and Teddy Goff.
In an article in the magazine Campaigns and Elections that appeared after Mr. Trudeau's big win, Ms. Dillon writes about the lessons from "north of the border."
"By winning Canada's parliamentary elections, the Liberals did more than buck conventional wisdom and post their best showing in 40 years," she writes. The party, she added – and much of the credit for this has gone to Ms. Telford – was "hard at work building the infrastructure necessary to run a data-driven, grassroots-focused, tech-savvy, and cutting-edge campaign long before the public, or the media was engaged."
A PLAN TO DELIVER
Some indications of the approach Ms. Telford will take in running the Prime Minister's Office can be found in an awkwardly named system of running government called Deliverology, pioneered by British bureaucrat Sir Michael Barber during the Tony Blair era. (Mr. Barber is attending the cabinet retreat in New Brunswick – that new Liberal bastion – later this month, and will brief ministers on his system.) Mr. Barber has kept in touch with Ms. Telford, and sent both Ms. Telford and Mr. Butts a copy of his new book, How to Run A Government so that Citizens Benefit and Taxpayers Don't Go Crazy, just after Mr. Trudeau won the election.
Mr. Butts first became aware of Mr. Barber while serving as Mr. McGuinty's chief aide, when the Briton was head of Mr. Blair's "delivery unit," which worked to ensure that major election promises were monitored and kept. Deliverology requires that a cabinet member or the prime minister check in regularly with public servants to see where they are in delivering a given promise and, if need be, to tweak what needs tweaking.
Ms. Telford and Mr. Kennedy employed the system when he was Ontario education minister. "We devised our own approach, but did learn from and adapt Barber's," says Mr. Kennedy. "While similarly tough-minded on targets," he adds, "our approach was a much more positive, transformational way of getting people onside than the Brits' name-and-shame outlook."
Still, the system has its detractors. In his 2008 book, Systems Thinking in the Public Sector, John Seddon, now a visiting professor at Britain's Buckingham University Business School, devoted an entire chapter to Deliverology, referring to it as the "so-called science of delivery as invented by Sir Michael Barber." He argues the system didn't deliver results in the U.K. "Instead, it established a coercive regime to force others to comply. … I think of it as Mickey Mouse command-and-control. That is being generous to Barber and unfair to the mouse."
Deliverology is clearly not a panacea. But Mr. Trudeau's – and Ms. Telford's – determination to apply its tenets to the federal bureaucracy seems to offer a clear sign that they hope to deliver on the promises they made during last year's campaign.
TALL ORDERS IN THE PMO
There are few who think Mr. Trudeau will have an easy time doing that.
And those who know how the Prime Minister's Office works say Ms. Telford will face her own challenges as well. Although her job is to run the PMO, she will also have to keep a steady eye on the public service, the cabinet, the caucus and the party. In the words of Ms. White, who served as Ms. Campbell's chief of staff all those years ago, after Ms. Telford's long road through politics, she is now "probably the last adviser to the Prime Minister."
As Ms. Telford embarks on the newest chapter in her career, Ms. White's advice also includes this: "Take care of your personal life, too. That would be definitely something I would say. It's a big part of it. Even if it was a man, I would say that."
That's another tall order for a woman who was instrumental in bringing Mr. Trudeau to power – and who will now be front and centre in ensuring that he gives Canadians the kind of government that makes them want to put him back there in four years' time.
Jane Taber is a political reporter at The Globe and Mail.