My legal colleagues invited me to lunch … at a strip club

Lessons learned as the first woman in the room

Being the first woman in a role has been a recurring feature of my career. Being the first woman in a role or the only woman at the table has been a recurring feature of my career.

I am proud of my achievements, and I know that they have come from a lot of hard work.  

But I also know that I did not get here alone.  

I can’t count the number of times I have walked into a room filled with 10 or 20 or even 50 negotiators, all representing their country, each with teams supporting them; and yes, virtually every person in the room has been a man. I am often asked “How did that feel?” or “Did you suffer from imposter syndrome?”  

The answer is: it felt great! Sure, sometimes there were the heart flutters of nerves, but by the time I was in those rooms, my internal voice was telling me: “You are here. You are speaking for Canada. You know what you are doing and that’s why you have this role.”

But I didn’t get to that place of confidence overnight, and I didn’t get there alone. And I recognize that while I faced barriers, there are others who face far greater ones. 

I didn’t get to that place of confidence overnight, and I didn’t get there alone.

Kirsten Hillman

It started with my parents. My mother taught me with her actions. Life wasn’t always easy; money was tight. She took a lot of professional risks, but she was true to herself and took pride in what she was doing. I saw that. My father’s unwavering message was, “You can do anything you put your mind to. Go give it a try.” It was simple, consistent, and powerful. I heard and absorbed it.

You can do anything you put your mind to. Go give it a try.

Kirsten Hillman’s father

These were the seeds of my self-confidence, but like all young people I had to learn through experience, trial, and of course, error.    

There are times I wish I had been stronger; when I should have spoken up. Like when, as a young lawyer in the private sector in the mid-90s, during all-hands-on-deck litigation preparation, the senior partner invited the clients and lawyers to lunch at a strip club.

They, all men, went. I, the only woman, ate lunch at my desk. I was angry. This lunch was a relationship-building moment for the other young lawyers, but not for me. Was this a test to see if I was “one of the boys?” Or was I invisible? I felt invisible. And, going back into a boardroom after lunch with a dozen men who had just spent two hours at a strip club, I felt unsafe.

But I didn’t say anything.

I think about that episode to this day — about how that could possibly have been considered to be okay, and also about why that young me didn’t say anything.

While I wish I had, I understand why I didn’t. Today that wouldn’t happen — certainly not in any workplace of mine. Today I’d speak up. But perhaps more importantly, I work every day to foster a workplace where others would, too.

The journey from then to now — from uncertainty to conviction — took time.

It grew from hard work and the courage to be true to myself, but it was also fueled by mentors and leaders who believed in me and trusted me. Sometimes these mentors told me things that were hard to hear. Like the senior law partner who said, “This path you’re trying to go down doesn’t suit you, and frankly, you’re not that good at it because your heart isn’t in it. You should try something else.”

Following that heart-to-heart, I ended up moving cities, changing jobs, and shifting my career to the public sector.  So, although the words stung, hearing them was in many ways a relief. That single, tough-love moment changed my career path and taught me a lot about listening to my inner voice.  

A single, tough-love moment changed my career path and taught me a lot about listening to my inner voice.  

Kirsten Hillman

But that was only the beginning. Keeping that inner voice strong takes effort. Proving that you can do the job, that you belong at the table even though no one who looks like you has been there before, takes time, a lot of hard work, and the strength of a well-functioning team. 

I’m a details person — a wonk, if you will. So, for me, confidence comes from being very well prepared, knowing the issues inside and out, and having creative ideas and solutions up my sleeve. In moments when I might fall prey to nerves or run the risk of seeing myself through someone else’s eyes, it’s knowing my stuff that builds me up.

Superpower of a great team

That’s where the superpower of a great team comes in. In my career, the periods when I have been the most fulfilled and the most effective are when I have been surrounded by smart, devoted, creative, and decent people, all pulling or pushing in the same direction. And so, in those moments when I was the first woman in a role or the only woman at a table, when I could feel the eyes of others telling me that I didn’t belong, I was never alone. We were all committed to each other and to mutual success.

In my career, the periods when I have been the most fulfilled and the most effective are when I have been surrounded by smart, devoted, creative, and decent people, all pulling or pushing in the same direction.

Kirsten Hillman

And, throughout it all — the weeks of travel around the world, the long hours, and the high-pressure environments, as I have taken risks and stretched myself — my greatest champion and indispensable partner has been my husband. 

I am very proud to be the first woman to be Canada’s Ambassador to the United States, and to be the first woman doing many of the jobs that I have done. I hope that women, or any other person from an underrepresented group, can look at me and say: “If she can do it, so can I.”

NASA astronaut Christina Koch — the first female astronaut to soon orbit the moon — says that she sees these “firsts” as milestones. A milestone is about forward momentum. It’s a point that marks progress. It’s important in and of itself, but it is also about pushing forward to the next milestone and towards the day when the next person exceeds it. That resonates with me.

by Kirsten Hillman

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.

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