Kirsten Hillman – Canada’s first female Ambassador to the United States

Kirsten Hillman is Canada’s Ambassador to the U.S. and the first woman ever to hold this role. In the past, she has also played a critical part in negotiating major trade agreements for Canada.  

Ambassador Hillman joined Jennifer and Catherine to talk about the preparation for President Biden’s historic visit to Ottawa and how the team at the Canadian Embassy to the U.S. was involved in the process. She also gave us a behind-the-scenes look at her career and talked about her childhood, mentoring women, and making choices around things that make her happy. 

Note: This transcript has been edited for clarity and length.

Kirsten Hillman, Canada’s first female Ambassador to the U.S.

Kirsten Hillman on mentorship and representation 

Jennifer Stewart: What do you hope, Ambassador, other people, in particular women, take away from knowing that there is now a woman in this role?  

Kirsten Hillman: I hope and I believe that representation in a r​ole​ like this demonstrates and tells others, whether it be women or other groups of Canadians who have traditionally had less access to some of the most senior roles in our society, that if you do the work, if you have the skills, if you can gain the experiences, if you are working towards an objective, like a position like this, that it is possible.

It doesn’t mean it will happen. But there’s a very important rule of demonstration that people can see themselves in other people, not because they’re put there because they’re a woman, or they’re a minority, or they are some other kind of group, but because they have the skills to do it, and anyone who has the skills to do it, and the experience and the expertise, can have some of these important roles. 

Catherine Clark: I’d love to talk to you about mentorship because you have talked about the importance of mentoring, both in terms of mentoring that you’ve received from other women, but also mentorship that you’re able to provide. What role mentorship has played in your life?  

Kirsten Hillman: It’s been very important for me in different ways. ​I​n my personal life, as a kid, I was raised by my mom. And most of the time, I lived with my mom growing up, and most of the time she was single and she was a small business owner. And she worked really hard. It was not easy, it was often actually really difficult for her.

But what I saw from her​,​ she left a career as a nurse because it wasn’t satisfying to her. She took some big chances. She took some chances on herself. And she was able to achieve something that gave her a lot of satisfaction, independence, and a sense of accomplishment. I know that that has had ​a​ very significant impact on how I think about how to make choices in my life.​ 

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Jennifer Stewart: Take me back to that little girl. If she could say anything to you now, what do you think? Do you think she’d be surprised by your role? Happy? ​W​hat would her reaction be to the prominence and success that you’ve gained?  

Kirsten Hillman: ​S​he’d be surprised. I think that little girl wants to be a ballerina; that little girl’s dreams did not work out for her. But this is very good, too.

There are different ways to fulfill your dreams.

Kirsten Hillman

But I did have a pretty strong sense of self always. And I attribute that to my mother, but my dad is terrific, too, and was always very supportive of me. And a lot of my work ethic comes from him as well. So I think that they filled me with love and confidence. They surrounded me with love; it filled me with confidence. And I don’t think I ever thought there were things that I couldn’t do. I just don’t think I would have conceived of this particular position. 

Kirsten Hillman Canada's Ambassador to US

Kirsten Hillman on her career path

Catherine Clark: How did you end up going from ballerina to lawyer, trade negotiator, ambassador? ​That’s a different path for sure.  

Kirsten Hillman: ​T​he ballerina dream was a bit squashed because I wasn’t good enough. I did not have a linear career path from high school to university. I thought I was going to be a professor. And then I decided I didn’t like that.

So I went to law school, thinking I’d be a law professor. But then​,​ by the time I ended law school, I didn’t want to do that. So I became a commercial litigator for a little while in Montreal. And I liked parts of that. I mostly ​liked​ doing public policy law. But when I was doing sort of the nitty gritty of commercial litigation, I didn’t really like that.

So I went to Ottawa​,​ and I got a job at the Department of Justice in international constitutional law. And that got me a bit on a public service public policy route, which I remain on today.  

​​And this is what I often say when I am mentoring, because I do an awful lot of mentoring here in Washington as well as, with young women in particular, in different places around the world. ​​​

T​he number one thing is, it’s important to make plans​,​ and it’s important to have a path that you’re going down. But it’s really important to check in with yourself to make sure that those plans still make sense to you.

Kirsten Hillman

And especially in your younger years, when you’re trying to figure out exactly who you are and what you like and what you don’t like 

Jennifer Stewart: ​Y​ou tried a few things you didn’t enjoy, you went down a few paths, and you had a moment that this wasn’t for you. So you’ve redirected. We have the societal narrative that once you’re in high school, you need to know what you want to do. How do we be more fluid with especially young people, and especially women, that listen, sometimes you’re going to try​,​ and you’re going to fail​.​ And that’s actually a really positive thing? ​     ​ 

Kirsten Hillman: I think we have to lead by example, I think we have to demonstrate changes, and embrace them and say this is okay. So showing young women and explaining to them ​the ​different changes that we’ve made.

But also when they make changes or seek to make changes, or do something and fail, then I’m not saying we necessarily celebrate it, but we certainly don’t see that as a negative. We see that as a natural part of people trying to find their way into something that is right for them.

And I think leading large organizations, leading large teams, if we’re not open to having people come in, or move around, or leave if it is not the right thing for them, then we’re not going to build strong teams, because you succeed when you have individuals who want to be ​part of your organization​, who are enthusiastic about being there, who feel like they’re contributing.

I think we just have to be open and accepting that people move and change and evolve. And that’s good. And we should embrace that. 

Kirsten Hillman

The challenges of working in a male dominated industry 

Catherine Clark: ​Y​ou’ve definitely ​led​ by example. But you have also done so in fairly ​male-dominated​ arenas when you are leading trade negotiations, ​which​ is certainly a domain largely dominated by men. We had a conversation with Ailish Campbell the week before she was appointed Canada’s ​A​mbassador to the EU, and she was telling us a story about how at trade negotiations, she would often be mistaken as a secretary. And she would just have to gently inform people ​that, sorry, she ​couldn’t get ​their​ coffee. I just wondered what your experience had been and whether you had faced anything similar and how you overcame that and maintained your confidence​.​ 

Kirsten Hillman: ​A​bsolutely, I experienced things like that. I was the first woman lead negotiator for major negotiations for the ​Trans-Pacific​ Partnership and had a role in the NAFTA renegotiations, but I also ​led​ our entire trade negotiating branch. So I was sort of Canada’s chief trade negotiator for the whole government. And there are many countries we would negotiate against where there wouldn’t be a single woman on the other side. I had experiences where I was the only woman in the room. We tended to have a few women on our side, but even on our side, we didn’t have as many women as we did do today.  

I was never asked to get coffee, but I did more than once have a man sitting beside me​ – ​ often older than me, because I also had some of these jobs fairly young – and the chief negotiator on the other side would look at the man when he was talking instead of looking at me. ​

Kirsten Hillman

T​hat happened more often than I’d like to remember. But here’s the thing: it lasts for a while, it lasts for a meeting or two. And then when you clearly are in charge of your delegation, when you’re clearly the decision maker, and when you really know what you’re doing, and do it well, then there is no choice. The other side must accept that reality and work with you. And so I would say part of it is just persevering. Having a team​,​ and I always had this always, that respected me as their leader. And that takes time, you have to build that. It’s not just given to you.  

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And there is something very powerful about representing your country. I wasn’t there trying to achieve a certain recognition for myself. I was there representing my country, fighting for what was best for us​,​ trying to get the best deal I could for Canada​.​ ​

Or ​when I was a lawyer​,​ ​representing​ our side of the story as best I could. ​S​o it wasn’t personal to me. And that gives you a level of confidence and a detachment from any treatment that was less than acceptable, because it didn’t matter. I wasn’t there to feel good about being Kirsten Hillman, I was there representing Canada​,​ as Canada’s voice, and I wasn’t going to let Canada down. 

Teamwork and balance in parenting 

Catherine Clark: You and your husband have both had very busy careers. You have ​travelled​ a lot personally with your career. It’s taken you overseas to live at one point. Could you talk to us about the importance of teamwork in parenting, because a lot of our listeners still struggle with how they – and Jen and I are careful about using the word balance, but how they manage both career family and the division of ​labour​ within their homes so that both partners can be effective professionals and effective parents. How did you go about this?  

Kirsten Hillman: I think for me the first and most important fact is that my husband and I, before we had kids​,​ we consciously talked about ​how we would run our family​,​ how we would manage our careers and family life. And we checked in on that throughout our entire marriage.

I have a remarkable husband, and I would not be doing what I’m doing today ​i​f he wasn’t my husband – his support in allowing us to have a truly ​co-parenting​ relationship.

Kirsten Hillman

But he took responsibility for that, as much as I did. That is why we have both been able to do what we’ve done. And I say this often to women in particular, it’s a really important decision who you decide to spend your life with. ​ 

I​ had moments where I was very much the parent. ​​​​​​​W​hen my first son was born, I took eight months of maternity leave. When my second son was born, I took two years off. I think that time that I spent with my sons was really important. Had I gone back earlier, I wouldn’t have been happy. If the consequence was going to be my career would slow down or go in a different direction​,​ I was okay with that. Because at that time, it was the right decision for me.

And when we moved to Geneva later on, and I had a much quieter career for about four years, ​p​eople said, ​“​Oh you’re not going to go to taking yourself off of a particular track.​”​ And I was okay with that. Because it was probably the most exciting time of our family life​,​ before our kids left home. It was amazing. We traveled and they learn​ed​ different languages. And we met all sorts of wonderful people. ​ 

​​​I​t’s really important just to make the decisions that make sense for you at the time. ​T​here were several periods within our family life when our children were young and at home, that I was doing more of the parenting. And then there were times when my husband was doing more of the parenting. And we both were very much on the same page.​     ​​ 

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Catherine Clark: I really appreciate that ​y​ou’re willing to share the good and the bad and the struggles, because I think a lot of times that women just forget that even if you’re a remarkable professional, you’re still a human being. And often​,​ we hide the human elements, and that doesn’t make it easier for anyone else trying to achieve success.  

It would be impossible for me to do anything that I do without being myself.

Kirsten Hillman

Kirsten Hillman: Well, I’ll be honest with you: it would be impossible for me to do anything that I do without being myself. ​I​t would take too much energy to try and fit yourself into a different ​mould​ than your own.​​ I believe women are stronger if they are authentic​,​ and what’s authentic to me is different than what’s authentic to you. But just like men can come in all different kinds of styles, ​​​​​​​s​o can we​.​

I think that is something I always try to impress upon young people​,​ young women in particular​:​ You’ve got to be true to yourself​.​ ​Y​ou’ve got to do what makes you happy, and if​ it ​stops making you happy​,​ you’ve got to change it​,​ because you only have one life right now. We’ve got to live it the best we can​.​​     ​​​​​​​     ​ 

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