Jason Tolland (LLB ‘95) and Robert Brookfield (LLB ’95) met at law school and competed together in the Jessup Moot - twice! They both went on to private practice before shifting to public service, served as diplomats, and now both work in international trade. When we asked if they’d be interested in talking to us, they asked to do so together, and we’re excited to share their interesting and complementary journeys.
You both did the Jessup Moot together twice – tell me about that experience.
Jason Tolland (JT): The Jessup was one of the best experiences I had in law school. It actually gave me an intellectual impetus that I found wasn't always there, because, of course, law is a practice, a trade. The Jessup gave me that exposure to the full scope of the law. It made me more aware of the practical client necessities of timing and product efficiency, things you really need to understand when you start billing actual clients.
Robert Brookfield (RB): For me, it was probably the best experience of law school, not only because the substance was interesting, but because I had the opportunity to learn skills like developing argumentation and teamwork in a real, practical way. Working so closely with professors like Karin Mickelson we had the chance to pick their brains in a way that we never would in class. Plus, while we didn't do well the first time, we did actually win the second time which was very rewarding.
After law school you both went on to private practice and then shifted over to the public service at Global Affairs Canada. What led you to make that shift?
RB: For me, the private sector practice was really the path of least resistance, in the sense that they offered me a summer job and then articles. I mostly did litigation, which I enjoyed, but I never really was passionate about private practice. And I was uncomfortable with the feeling that I wasn't always contributing to society and working on areas of law that were most meaningful to me. I'd always been interested in living and working abroad and I'd already applied for the Foreign Service a few times but never got in. But then my then girlfriend, now wife, got a job with the Foreign Service so, I tried one last time and made it.
JT: Even before law school, I was really interested in environmental and social issues, and how many of these issues were married under the law. The law school had just launched its Indigenous Legal Studies program, and I was really struck by the divisions within the student population – I wondered how you could use the law to try and address those divisions. I also got involved with the HIV clinic in downtown Vancouver and was immersed in the social and legal questions around sex workers, and helped found a law and policy group to consider our ability to influence local legislation on environmental and social issues (NB: we didn’t change the world). These kinds of social challenges really piqued my interest.
When I went into private practice, I had the same challenge as Robert. Working in labor and employment law, I found that I often had to make ethical choices about who I was supporting and why I was supporting them. When an acquaintance suggested that I consider working in the public service, it didn’t strike me as the right fit. I am not, by nature, a “bureaucrat”. But the issues were really interesting, so I took the leap – and it proved to be fascinating. I have the opportunity to work on really interesting files at a high level, and then do something else. For me, that’s a significant draw.
You’ve both shared what drew you into working with the foreign service. What were the challenges you faced once you settled in?
JT: Working in the foreign service is very challenging for families. Even something as basic as where your child is going to be in school at the end of the school year becomes an uncertainty and that brings along an enormous amount of stress. Sometimes I think maybe it would have been nicer to have been a partner in a law firm and know where my car is going to be at the end of the day! But the upside is the fascinating stuff I get to work on every day. The opportunity to do something different when I take on a new post builds a unique perspective that I would never have if I were working in the private sector.
RB: Another challenge is how to jump into a new area where you're not an expert. Part of the job is moving around on a regular basis, so suddenly you've got to learn all there is to know about Djibouti, and you've got to be briefing a minister on Djibouti, which you know little about. Getting up to speed quickly is a challenge – but a challenge that I quite enjoy.
So you need to adapt quickly – but I imagine the circumstances around you can also change really quickly as well.
JT: My first posting was at the beginning of the 2000s. I originally wanted to go to the Cote D’Ivoire, which had been extremely stable. Then suddenly the French Foreign Legion was there, the government collapsed, and it was declared a crisis zone. So I thought I had landed in paradise when I was sent to Buenos Aires instead, which, at the time was the seventh most-expensive capital in the world. But during my posting, the cost of living slipped from 7th to 170th; it was a car crash of horrible economic and social proportions. There was genuine worry about anarchy. At one point, there were people dying in the streets, literally outside my apartment. There you see the hard edge of diplomacy. One day I was talking to the Minister of the Economy about closing a Canadian bank. Then on the way home, I saw the bank having its windows smashed by protesters. The next day, the president of the Canadian bank in Argentina was seeking asylum in the embassy and the embassy had to be surrounded by riot police because of protesters claiming their savings had been stolen by Canada.
Professionally, it was an incredible experience: I have never had more attention from the Deputy Governor of the Bank of Canada, the head office at the World Bank, the Deputy Minister of Finance - all of them were reading my reports. But not because they were mine; they were reading reports about the collapse of a country. That taught me an enormous amount of perspective about the work that we do, why it's so important, and the humility required to do it well.
Robert, I understand that you have also done some work with Justice Canada. Could you tell us about that transition? What kind of overlap - if any - exists between trade law and criminal law?
RB: When an opportunity came up to move over to Justice Canada I jumped on it, wanting to try something different. I actually felt the value I brought to the job was NOT knowing about criminal law, but I was able to A) manage lawyers and B) manage issues. I learned a lot about criminal law, how the criminal justice system actually works. I learned that whenever someone says there ought to be a law, federally, they go to the criminal code. So the weirdest things, from usury to animals in captivity to, witchcraft or foreign interference have an element of criminal law in them.
But while working in criminal law was really interesting, it really wasn’t about the type of law, but more about finding the balance between knowing enough to be able to engage those at the higher level but also trusting your team to do the detailed work, pushing them in a way that distills advice in a practical way that supports the decision makers or those who are communicating the information. Working in the public sector has allowed me to learn how to do this.
JT: I don't think diplomacy is changing, but the administration of diplomacy is changing. There are lots of actors in the international sphere, including think tanks and various for-profit and not-for-profit entities, and that's different than it was a generation ago. That means there are more opportunities outside of government to do the kind of work that Robert and I do. But it also means that people are looking at this less as a life career than perhaps they did before.
You are both currently working in international trade, which is currently in a major state of flux. What would you say are some of the biggest challenges or issues that you're facing right now?
JT: Diplomacy is not about certainty, right? A lot of the day-to-day diplomacy, certainly in bilateral regional relations, is short wave. There are a lot of specific issues, an earthquake there, a border incursion somewhere else, and you have to address it. Then international development work is done in a medium wave. But international relations generally is a long wave, with this sort of certainty of structures. It would be an understatement to say that, in terms of our relationship with the United States, we have lost some of that certainty. Our long wave is much more wobbly than it would normally be. It’s additionally challenging because there's a lot of white noise in diplomacy these days with the increasing number of communication channels and the speed at which they convey information.
RB: Speaking a bit more prosaically, the challenge, I think, is balancing practical advice while potentially dealing with earth shattering changes. For example, in my previous job, where we were renegotiating NAFTA with the first Trump administration, there was a lot of views that we had about what our trade agreement should look like that were broken because the Trump administration was not interested in them. So how do you adjust to that?
Jason Tolland: Jason was most recently DG for South American and Inter-American Affairs, overseeing political, economic and assistance issues bilaterally and regionally. He was also Executive Director of the Trade Law Bureau of the Government of Canada, working as counsel or negotiator on various free trade negotiations and disputes before the World Trade Organization. Overseas, he served as Ambassador to Finland, and was posted to Washington DC, Berlin, and Buenos Aires. Previously, he worked in private practice in Vancouver and as a consultant in London, UK. He now goes into professional exile as the spouse of another (likely better) ambassador.
Robert Brookfield: Robert is Director General (DG) at Global Affairs Canada, managing Canada’s export and import permit control regime. Previously he was at the Department of Justice for four years as DG and before that Deputy Assistant Deputy Minister, working mostly on criminal law policy. For more than five years he was DG of the Trade Law Bureau of the Government of Canada. He led the CUSMA (formerly NAFTA) legal team and has acted as counsel or negotiator on many free trade negotiations and disputes before the World Trade Organization, and was posted to Canada’s mission in Moscow. Before joining government, he worked in private practice in Vancouver.
First published on July 24, 2025.