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There was no three-year career plan. No five-year plan. No 10-year plan. “My career was very iterative,” says Kirsten Hillman. “I would do something, and if I liked it, I would continue along that road, and if I didn’t feel it was a good fit for me, I would shift into something else…It was like a process of refinement.”
She first “got the bug” for managing complex international relationships in 1994 at the age of 29, Hillman says.
After graduating from McGill University with a degree in civil law and common law, she practiced at now defunct McMaster Meighan, working on Charter litigation cases. But she wasn’t fulfilled. A mentor suggested she might be happier working in public policy law so she moved to the Department of Justice. Years later, along came an opportunity to work with Foreign Affairs on a one-year loan to help draft environmental treaties. “The first meeting I went to internationally was in Nairobi. And it was a UN meeting, so hundreds of countries. I’m just a drafter…I was just blown away by the people from all countries, many of them in their traditional dress, intervening and talking about this particular treaty that we were trying to negotiate from their perspective.”
When she heard about a new legal litigation section for cases related to the North American Free Trade Agreement (NAFTA) and World Trade Organization (WTO), “I kind of put my hand up,” she says. From there, she ended up as Assistant Deputy Minister of the Trade Agreements and Negotiations Branch of Global Affairs in Geneva. Once back in Canada, the Harper government asked her to help with the Comprehensive and Progressive Agreement for the Trans-Pacific Partnership (CPTPP), of which she was later appointed chief negotiator.
“The complexity is very interesting,” she says when asked to explain the intellectual draw. “If you think of a spreadsheet, you’ve got 12 countries and you’ve got 300 issues . And you’ve got to find a way to get them all aligned sufficiently to create a whole. On some issues, it’s very easy. And on others, it’s super hard.”
Much of the skill is empathy. “I’m a good listener, putting myself in the shoes of the other. And then you understand that well enough to do what we need to do for our country.”
She also loves leading a team. “The job of the lead negotiator is kind of like a symphony conductor. You’ve got to lead people who are running different things, and so it’s about giving them the freedom and making sure they understand your expectations in terms of when to check back in.”
In 2017, Prime Minister Trudeau sent Hillman to Washington as Deputy Ambassador. Two year later, she was appointed Ambassador, the first woman to hold the position. She played a key role in NAFTA renegotiations in Trump’s first term, managed during the Covid pandemic and worked with officials to release Michael Spavor and Michael Kovrig from detention in China.
The married mother of two sons was named one of Washington’s most powerful women by The Washingtonian for three consecutive years. She was also awarded the King Charles III Coronation Medal for her contributions to Canada. She stepped down earlier this year, a decision she stated to Prime Minister Carney when he asked her to continue after his election last spring. The timing was to give Mark Wiseman, the new Ambassador, and The Honourable Janis Charette, the next Chief Trade Negotiator, months to organize before talks begin in earnest.
“The job of diplomacy is the job of communicating. Communicating the interests of our country. Finding common cause. And [identifying] where we need to stand up and push back.” Those discussions involve not just the secretaries of the American administration’s cabinet but also members of Congress, Governors and leaders in the business community.
Behind the scenes, the relationships are more cordial than headlines suggest. “I know this might sound hard to believe, but I had a lot of very effective relationships within the Trump administration. They have their boss’s agenda to pursue. But, a lot of getting things done is about having relationships of trust, or at least relationships where you have achieved certain things together in the past, or where you have a certain amount of common cause…That may not result in the kind of success that we would always want. But it may mitigate other risks, and it may lead to certain successes.”
Hillman’s time as U.S. ambassador has “completely shaped who I am, not just my professional identity, but my personal identity,” she says. “It’s made me quite fierce when it comes to our country. That’s how I would put it. We’re a humble nation, right? We are somewhat reserved, less reserved now, granted. But we are somewhat reserved. But when your job is to defend Canada, to speak for Canada, to express our views, to always be the one at the table that is making sure that our voice and our interests are being heard, whether it’s in a court, or at a negotiating table, or as an ambassador, it’s not the time for timidity…Obviously, we are respectful people, but it is the time for clarity of purpose, for strength, for self-confidence, for national pride.”
“If you’d asked me 15 years ago, I would have been like, yeah, I love my country. But now for 8 years, I’ve been thinking about our nation, and where it sits, and what’s good for it, and where we need to kind of up our game, and where we need to be stronger in our voice. So that’s what I mean by ‘it’s shaped me.’”
Currently, the Winnipeg-born public servant is entertaining several possibilities for next steps, none of which she is willing to disclose. She recently accepted a senior fellowship at The Munk School of Global Affairs and Public Policy. She also wants to spend more time with her aging parents. But otherwise, “we’re going to see where the winds take us.”
Asked if a post-Trump world will return relations to the way they once were with our American neighbours, she responds emphatically, “We won’t go back. Nor should we. Life’s made for moving forward. We’ve learned important things about ourselves, about this relationship, about where we fit in the world, about our vulnerabilities, about our resilience, and we need to take that into account. And as we take that into account and govern ourselves accordingly, necessarily the relationship will change.”
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Inez Jabalpurwala, President and CEO of the Public Policy Forum
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