Keeping her ‘eye on the ball’: Hillman reflects on her time as top diplomat in D.C.

U.S. President Donald Trump, left, pumps his fist as he is greeted by Kirsten Hillman, Canadian Ambassador to the United States, right, as he arrives in Calgary, Alta., Sunday, June 15, 2025, to attend the G7 Leaders meeting taking place in Kananaskis. THE CANADIAN PRESS/Jeff McIntosh

WASHINGTON — Kirsten Hillman hasn’t written her autobiography yet, but the 57-year-old career diplomat — soon to be Canada’s former ambassador to the U.S. — may already have a title picked out: “Diplomacy is a contact sport.”

One glance at her CV tells you why.

She has been the underdog staring down centre ice as the world’s largest economy looks to tear up Canada’s critical trade pact. She’s been the quarterback directing plays to keep trade moving during a global pandemic.

And she’s been the goalie, deflecting shots as U.S. President Donald Trump calls for Canada’s annexation and addresses its prime minister as “governor.”

“You just have to keep your eye on the ball,” Hillman said when asked what advice she would have given herself at the start of her tenure.

“What exactly is our job here in Washington and across the country as Canadian diplomats? Our job is to do the best that we can … get the most that we can for Canada on every individual topic that comes up.”

There will be distractions and diversions, Hillman said, “but we just keep plowing through.”

Hillman grew up in Calgary and Winnipeg. Before coming to Washington, she earned a reputation across party lines as a knowledgeable civil servant and trade policy expert.

She served as Canada’s senior legal adviser to the World Trade Organization and as Canada’s chief negotiator for the Comprehensive and Progressive Agreement for Trans-Pacific Partnership.

She came to Washington in 2017 to serve as deputy under then-ambassador David MacNaughton during the first Trump administration — just as the president was threatening to tear up the North American Free Trade Agreement.

Negotiation of the Canada-U.S.-Mexico Agreement on trade, which replaced NAFTA, was a key test of Canadian diplomacy. Robert Lighthizer, Trump’s trade representative at the time, recounted in his book how at one point during the process the two countries weren’t speaking — and “NAFTA was hanging on by a thread.”

Ultimately, the new deal, better known as CUSMA, was signed to much praise by the governments of all three countries. That deal is up for review this year and Trump’s public comments have suggested it could be a lengthy, hard-fought negotiation.

The CUSMA experience left Hillman with a clear sense of the pitfalls of diplomacy in the Trump age that served her well after she was named ambassador in 2020 — the first woman ever to hold the post.

The challenges came at her quickly. There was the COVID-19 pandemic, the new Biden administration to navigate and a growing number of global crises. She worked with Washington to secure the release of Michael Spavor and Michael Kovrig from detention in China.

Now, Hillman said, Trump’s return to office has made the relationship with Canada’s largest trading partner and closest neighbour even more complicated.

Hillman has a reputation in Washington for being able to navigate both Republican and Democrat spaces. The Washingtonian, a monthly magazine, has named her one of the most powerful women in D.C. multiple times, including last year.

Hillman said, no matter who sits across the table from her, her job is to listen and look for common ground. That doesn’t always mean accepting the median position as a compromise, she said.

“Diplomacy isn’t about finding a compromise position,” she said. “It’s not about taking sort of Canada’s view and America’s view and watering them both down and finding something we can both live with. That’s not what it’s about.

“Representing your country in another country is about … pursuing your country’s interests, trying to minimize risks, but doing so in full faithfulness to the values of your country.”

Hillman has travelled across the United States and makes a point of meeting people on all levels of government. It’s nobody’s idea of easy work but it matters — now more than ever.

“I’m so deeply proud of our country and I’m so deeply honoured to have this role in trying to lead our overall relationship with this country,” she said. “And even when I’m exhausted, I fall back on that and I think, ‘OK, this is really important.’”

The important work isn’t always the kind that makes headlines. Hillman said she remembers correspondence from people and companies looking for help navigating problems ranging from contracts to cross-border water issues.

She said she’s received a lot of emails over the past year thanking the embassy team for navigating the unprecedented turmoil of the second Trump administration.

“I’m blessed,” Hillman said with a wide smile. “I really am.”

Deciding to step away wasn’t easy, she said. She spoke with Prime Minister Mark Carney about staying on after his 2025 election win to help with the transition, but indicated that her time in Washington was winding down.

“I also want to start a new chapter in my life,” Hillman says.

While a return to Ottawa — and a much-needed vacation — could be in her immediate future, Hillman did not say what her next career move might be.

Carney appointed global investment banker and pension fund manager Mark Wiseman as Canada’s next ambassador to Washington. His term begins Feb. 15.

When asked what advice she’d give her successor, Hillman said it’s important to collaborate.

It’s “not a one-person job,” she said. “This is a team effort, and it’s a heck of a team.”

Diplomacy means meeting people where they are at, she adds. Any Canadian diplomat in Washington should carve out time to meet with people outside the Beltway bubble — the governors and businesspeople with a vested interest in a healthy Canada-U.S. relationship.

“Understanding who America (is) requires leaving Washington, D.C.,” she said. “That’s for sure.”

Kelly Geraldine Malone, The Canadian Press