Women Trailblazers in Canadian Restructuring Law

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Jenna Willis: Welcome to this episode of the Blakes Sound Business podcast. I’m today’s host, Jenna Willis, Counsel in the Blakes Restructuring & Insolvency team. In today’s episode, I’m joined by three women I’m proud to call my colleagues. They are trailblazers in the restructuring industry — Blakes Partners Pam Huff, Milly Chow and Kelly Bourassa. Together, they bring more than a whopping 90 years of experience. They hold numerous leadership roles at Blakes and across the industry, and have earned multiple awards and top-tier rankings for their work. They are all also mothers, balancing demanding careers with life outside the office. Pam, Milly and Kelly have each played a key role in making Blakes a market-leading, Band 1 restructuring team. In this episode, they’ll share their experiences, insights and some lessons learned, and offer advice for those of us building careers in this fast-moving and complex area of law. 

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Okay, Pam, let’s get started with you. You’ve been practising for over 35 years and have held an extraordinary range of leadership roles. To name a few, you’ve been the president of the Insolvency Institute of Canada, and its first female president. You’ve been the chair of the Ontario Bar Association’s Insolvency section. You’ve been recognized by the Turnaround Management Association as a trailblazer for women in restructuring. You are the first and only Canadian inducted into the International Women’s Insolvency and Restructuring Confederation Hall of Fame. You’ve also served on the Blakes Executive Committee and as the Practice Group Leader for our national R&I team for over a decade. So with all of that experience behind you, could you kick us off with some reflections on how you’ve seen the restructuring world evolve over your career?

Pamela L. J. Huff: Oh, thank you for that introduction and for revealing that my contribution to the collective 90 years is a whopping 35 of them. I started out in restructuring in the late 80s, early 90s. And that really was the start of the restructuring and insolvency specialty practice that has developed both at Blakes and at other law firms in Canada. We’ve been focused on interest rates in the last couple of years in our current economic situation, but it’s a time to remind everybody that in the late 80s and into the early 90s, interest rates rose, Bank of Canada raised its key interest rate from an annual average of 8.4% in 1987 to a whopping 13% in 1990. Just like now, the rise in the interest rates was intended to fight inflation, which was particularly acute in the housing market. And it led to quite a lot of work for restructuring professionals. And so, what was really born in the recession of the early 90s was the specialized restructuring practice that we know of now. The last 35 years has been a period of tremendous growth in the practice, and Blakes has been at the forefront of that, both as thought leaders, as practitioners, but the playing field has very much changed in that 35 years.

Jenna: And Pam, how would you say that change has been felt specifically by women in the field? 

Pamela: So, there were a few of us women that started out in that practice in the 90s. The most significant development is the number of women that I have seen since then who have embraced this practice which, I think we’ll talk about over the course of this podcast, has its challenges both on the work side and the home side. It is — as those of us who do it understand — it’s a bit of a fire drill from time to time. You don’t always know how your time is going to be spent every day or every week or every month, for that matter. It is something where I’ve seen a huge growth in the number of women who are embracing the practice as well, which is very gratifying to see, including my partners on this podcast today. So, Milly and Kelly, we are a part of that move of more women in the practice that has continued to evolve, particularly on the lawyer side, a little less so on the financial advisor side. But certainly, on the legal practitioner side, there’s been a huge growth of women that are embracing this career path.

Jenna: Thank you for that, Pam. So, Milly, as Pam said, you’re another woman who has fully embraced the restructuring career path. You bring more than 30 years of experience to this conversation, including significant leadership roles as president of the Turnaround Management Association’s Toronto Chapter and on the international stage as the TMA’s global chair and global president, where you were the first Canadian woman in that role. You’ve also been inducted into the TMA’s Turnaround Restructuring and Distressed Investing Industry Hall of Fame. Can you share with us, Milly, what motivated you to pursue all of those positions? And how has the time and energy you must have invested in those roles helped to shape your career?

Milly Chow: At the time I started what I call my TMA journey, I had three kids under 10 and a very busy practice. Free time was just not a thing. And so, the decision for me to pursue leadership opportunities at the TMA, initially at the local level and ultimately at the international/global level, was a very conscious strategy for me because I recognized that, you know, after spending years working hard while raising kids, what I was missing was profile in the industry and being seen as a leader by my peers. And I wanted to change that perception that all I was was just a good and smart lawyer. So, I sought out more leadership opportunities, not only on files, but also in the restructuring industry more generally. And it wasn’t easy. The boys were older, but Ben, my youngest, was still only about two years old when I started volunteering and, you know, as every parent knows, it doesn’t get easier or less time-consuming just because your kids are older. And the file work and client demands also don’t just decrease because I’ve decided to take on volunteer leadership opportunities. Was it worth the investment or sacrifice? Absolutely, without a doubt. Being part of the TMA Toronto Chapter leadership was very helpful in building my profile in the Toronto restructuring community. And the leap to the TMA Global leadership was even more impactful, leading an association with a global platform. I think at the time they had 9,000 members and, you know, I think 52 or 53 chapters around the world. You know, that was not only a significant responsibility for me, but it was also an incredible opportunity, and it has made a meaningful impact on my career. So, I would absolutely encourage young professionals to make the investment to seek out leadership opportunities in volunteer associations. It will expose them to a wider network of professionals than they would otherwise meet on file work, it will help them build their profiles in the industry, hone their leadership skills, and it will be an incredibly rewarding experience for them both professionally and personally.

Pamela: And Jenna, if I could add to that and just tie in Milly’s comments with my earlier comments, this all happened in the last 30 years. The TMA started in the early 90s. We at Blakes, we wanted to be the best restructuring team in the country. And there was this period of enormous growth in the industry, but also in the practice, in the legislation, in the policy, that was really framing the restructuring tools that were going to be available to companies. It really did turn things around. And part of what Milly was doing in the TMA, and Kelly and I were also doing in the TMA and other organizations, was to be part of the thought leaders. To take those leadership roles because we wanted to be involved in shaping the policy for restructuring practice in Canada. The three of us were there for that wave.

Jenna: And speaking of shaping policy, Kelly, that brings us to you. You have 25 years of experience. You are the co-leader of the Blakes national Restructuring & Insolvency group. You’re the current president of the IIC, and only the second woman to hold that role, as Pam’s successor, and the first person from Western Canada to hold that role. You’ve also served as president of the TMA’s Northwest Chapter. And you joined Blakes in 2007, after some time at other firms, and a period working in policy with the Senate of Canada, which is a different path than Pam or Milly, who are Blakes lifers, as we call it. Was there a particular file, or experience, Kelly, that played a defining role in shaping your career path?

Kelly Bourassa: I think for me, my very first debtor file was clearly — and anybody who does restructuring knows — that that’s the file you want. Debtor files are the most fun, the biggest fire drills, they’re ensconced in cloak and dagger at the beginning because, of course, it’s so confidential and nobody can know. And so, I had done a lot of work-out work at my first firm. And then when I changed firms to move out to Calgary after I was first married back in early 2000, I remember that vividly as being the real turning point of, like, you can never do anything else. And to your point about my path having been quite winding, I’ve moved back and forth across the country, almost always for personal reasons. And then picked up my career and started again. And when I was in Ottawa, I decided I didn’t want to practise any other kind of law other than restructuring. And there was really no restructuring to practise in Ottawa. And this was obviously long before all of the remote options that we have post-COVID. And so that’s how I ended up with the Senate. I was talking to someone at a cocktail party, talking about some of the work that I’d been doing in Calgary on a big file at the time that I was not at Blakes. And he was like, “Wow, you were involved in that? We need you at the Senate to advise the policy direction for the two chairs of the Senate Banking Committee.” But getting to shape the practice, to Pam’s point, I actually, while at the Senate, had the benefit of being part of the Sunset Clause review, which was undertaken in 2003, but the amendments weren’t ultimately brought in until 2009. So, the current CCAA, BIA, that we work from, those amendments came from the work that we did in 2003 and were kind of added upon. But, like not being interested in practising other kinds of law, I also wasn’t interested in doing policy forever. And so, after having my kids and doing my master’s and wanting to come back to private practice, that was when I knew I had to go back to a firm that I could do that kind of exciting restructuring work at. And that’s how I came to be at Blakes.

Jenna: That’s a very interesting background and path, Kelly. Pam, is there a particular file or experience that you would say was pivotal in shaping the direction of your career?

Pamela: I would say that everybody has what I call their breakthrough file. There is in your career at some point one file where you are able to take centre stage, where it’s complex, usually there’s difficult competing interests. It’s not going to be easy, and you have the role — whether that’s as debtor counsel or as monitor counsel or as key lender counsel — to really take the stage and meaningfully direct the process and take leadership in the process, and have effectively the community with which we all work, the other lawyers and financial advisors that work in the industry, recognize your talent. And for me, that was the Red Cross restructuring for sure. And I was on for the hemophiliacs. In that case, it was a strange combination of personal injury lawyers who were our class action counsel for various groups of plaintiffs, and then the government and what it was going to do. And it resulted in a very favourable settlement for everyone, but also was the beginning of the Canadian Blood Services, which was taken out of the Red Cross as a standalone entity. And so, my expertise as a restructuring lawyer was central in that file, in that negotiation, and it allowed me to really take centre stage. There’s always that file where you think, this is where I can really show how good I am and what I can do, and that was the one for me. I call it the breakthrough file, because there’s always one where you’re not any longer the support. You’re not the one adding value behind the scenes. You are absolutely frontline and, quite frankly, loving it.

Jenna: And Milly, what’s your pivotal career-direction-shaping story?

Milly: So I want to take a slightly different perspective on the question, and come at it not focused on a particular file that shaped my career, but I’m gonna go all the way back to my decision to devote my practice to restructuring law because that was absolutely not on my radar at all. I don’t know what I was thinking back then, but I wanted to be a constitutional law lawyer. And then as part of the Blakes articling program, I got allocated to what was then called the Creditors’ Rights group. I had absolutely no idea what that was, but, while I was there, I worked under the mentorship of a partner who was more of a financing lawyer, and realizing that there was no constitutional law practice in my future, I enjoyed that experience enough to go back to that group as an associate where I practised mainly financing law, with some work-outs here and there. Then in my second year as an associate, one day, late in the afternoon, another partner in the group — he was core restructuring, a restructuring litigator — came into my office in a panic and he said, “I need your help, and I need you to come with me right now. We’re going over to another law firm’s office and we need to negotiate and finalize a transaction that day,” because there was a court imposed deadline. And, I was thrilled at the opportunity, but honestly I was a bit panicked. I confessed to him that I never actually worked on a purchase and sale agreement before, but, of course, always up to the challenge. And remarkably, that didn’t seem to faze him one bit. And so, off we then trotted to the law firm’s office and we spent the entire rest of the day there until the very, very wee hours of the morning, hammering out that transaction. And there were like 10 of us in the boardroom for hours on end, and we had no choice but to be there and get, you know, things done. And it was real-time negotiations and decision-making, and there were real consequences to the decisions that were being made throughout the night. It was incredibly exhausting, but also invigorating at the same time, and I think every restructuring lawyer knows what I’m talking about there. And from that moment on, I would say I was hooked, and I knew that restructuring was where I wanted to be.

Pamela: It’s either hooked or run for the hills. But I think, you know, for those of us on this podcast, that is what we love about the practice. The urgency is just part of the excitement, the importance of what we’re doing, that we’re actually working on a very urgent and immediate basis to solve a problem that can be very significant, both for employees, for customers, for the economy. It’s something that really energizes us, and it’s something that I think that you stumble upon because you don’t really realize what the insolvency practice is like until you have that first opportunity to engage. And once you engage, Milly, like the story that you told, you realize that this is something I want to do, and it’s no longer a job, it’s a vocation.

Jenna: I think that’s exactly right, we all seem to have a similar story where we get hooked on restructuring work. Shifting to a female-focused question, as women who have built very successful careers in this industry, have you faced any particular challenges or barriers along the way?

Pamela: So, I’ll start because as I said in my first comments, the practice has really changed quite significantly in terms of the number of women that are engaged in it now compared to when I started. But, I do think that the challenge that women face in pursuing their careers in insolvency is the client development side of it, the business development side. So, trying to find a way to connect with the client base, which continues to be predominantly male. And to connect with that client base in a meaningful way in business development activities has been the number one challenge for women in the industry. When I started out in the practice, one of the major client activities was golf, which continues to be the case. And I didn’t play golf, and I watched all of my male colleagues go off with our male clients and play golf. Seemed like they could go all day and do that and have dinner afterwards and spend a lot of time together. And I really felt like I needed to get in on that game. So, I took some golf lessons in order to participate and then realized how hard the game is. And 35 years later, I am an absolute addict, but I learned how to play to a level of adequacy because I wanted to participate in the kinds of client development things that my male colleagues were doing. I wanted to be on equal footing. And so being able to play golf was one of the things that I embraced. 

I think when we’re talking about challenges to, you know, three women who are all mothers — and one of the challenges is obviously balancing home and life and work. One of my other mantras, Milly, I’m sure you’ve heard it from me, is just embrace chaos. What we do is not a job. As I said, it’s a vocation. We want to do it, and we want to be the best at it. And so, as a result of that, there’s going to be a lot of time and energy put into being the best restructuring lawyer that we can be. And that goes for any job that anybody pursues. If you want to be really good at something, it’s going to take a lot of time and effort. And if you have a family, that’s going to take a lot of time and effort, too. And both are extremely rewarding, personally, but they take a lot of time and effort. And you can’t think about your life anymore as a report card, where you’re trying to get an A+ in every subject. You’re just trying to be as good as you can be at the office and as good as you can be in your family. And everything else can kind of get a B-. And remember that the important things are work and family, and everything else will somehow get itself done. And don’t hold yourself to unreasonable expectations that everything you do is going to be an A+ in every subject of your life.

Kelly: Which for a bunch of AAA+ people is challenging, right? That is the challenge.

Milly: You know, crisis doesn’t wait for us. So, we need to either embrace the chaos or we learn to filter it out. I’m not sure if Kelly will remember this because it was many years ago, when Kelly’s kids were still quite young, and we were on this just ridiculous file. We had to do the impossible in a very short period of time. And we were on endless calls trying to, you know, figure out what we needed to do and develop the strategy. And I remember one particular afternoon, we were on a call, and Kelly’s kids were in the background, constantly screaming and vying for her attention. And after the call, one of our male colleagues, who didn’t have any children at that particular time, mentioned to me afterwards, and he was quite perplexed about how we were able to work and focus and concentrate and still sound intelligent in what he had described as pure chaos. And the answer I gave him was because we learned to filter out the chaos, because we have to. You know, we, especially as restructuring lawyers, we work evenings, weekends, holidays, vacations. We just do what we need to do.

Jenna: That’s such a good way to put it. Sometimes we just have to do what we have to do, and maybe that means embracing the chaos and not doing the A++ job in every aspect at every moment. Continuing our focus on women in restructuring, I’m obviously here speaking to three senior market-leading women in restructuring. And Blakes is one of the very few firms in the country that has this many senior women leaders in our industry. So, from your perspective, has Blakes done something particularly well to support your advancement? Have there been mentors or allies who played a meaningful role in your career?

Pamela: Um, maybe there’s something in the water. One of the things that I believe is influential in how our careers have all developed is that Blakes really is an entrepreneurial firm. It’s not hierarchical, and it’s very much a meritocracy. And when you put those three elements together, then gender is a little less relevant because what you do and the pursuit of your career — the results speak for themselves. And so, at the very base level of it, Blakes entrepreneurial mindframe of encouraging associates, partners to pursue their careers, to be the best at their jobs that they possibly can, was very beneficial for women coming through the practice. At a time, I was really the first wave of 50% of women out of law school. So, there were lots of women coming into the practice, and Blakes was attractive to me. I’m a lifer, as you said, Jenna. That entrepreneurial mindset at Blakes was very attractive to me back then when I made my choice to article at Blakes. And in terms of mentors and allies, yes, I did have the benefit of that. And I was lucky enough to work with a litigator, Don Brown, who was really, you know, gender-blind. He worked with men and women, and he didn’t particularly care what your gender was. He just worked with associates that wanted to be part of his practice. And he was the epitome, to me, of what I thought a litigation lawyer should be. And I loved going to court with him and seeing how he interacted with the judges. And so, I would say there were two factors for me that I thought Blakes provided. One was just the general entrepreneurial spirit of our firm. But also, I did have the benefit of, right from the very beginning, working for someone who was hugely promotional in terms of my success as a litigator and who was also the partner that suggested that I join this burgeoning Creditors’ Rights group, as it was called back then, now the Restructuring & Insolvency group. He was the one that gave me the advice that this was a new practice area, a new specialty area. There was going to be enormous growth and opportunity in it, and thought it would be a good idea for me. And so his advice took me on the path that I have now spent the last 35 years on.

Jenna: I want to pick up on a comment that you made there, Pam. You said that maybe there’s something in the water. I can say personally, I have found it very valuable and important to have female colleagues and mentors, including yourselves, during my career. How meaningful has it been for each of you to go through your careers alongside each other, fellow women and fellow moms?

Kelly: I’ll jump in first. So, having been the only lateral to Blakes — and Pam reminded me of meeting her for breakfast when I was still considering the Firm and considering moving back to Calgary, and the advice she was given was not to screw it up. Well, she didn’t. But working with Pam, working with Milly, working with other members of the team, it is, Blakes is a special place. It’s the first of the firms that I’ve worked at that I actually wanted to become a partner. And I think there were a lot of reasons for that. The female leadership, I think was for sure part of it because that is very unique to Blakes, and it was even more unique 17 years ago when I joined. But I think also as we’ve worked on files together — the three of us, sometimes all three of us, sometimes a subset — it’s a complete understanding of the juggling that we’re each doing and the, “I’m going to go offline for two hours so that I can feed my kids and put them to bed,” but you’ll be back on and then a back and forth, and it becomes seamless. And the number of times I’ve been at the ski hill when my kids were taking ski lessons or at a dance class or a soccer practice and talking to somebody else on the team, including Pam and Milly, who are often doing the same things. It’s too many to count.

Pamela: And we have, the three of us have had the opportunity to work all together on files and we’ve done that for many, many years now. Earlier on, when I didn’t screw it up and successfully had breakfast with Kelly and persuaded her that Blakes was a place for her, we did work together, and Kelly, at that point in time, you had your twins and a daughter — you had three daughters under four. And with the two-hour time difference between Toronto and Calgary, we were able to arrange it so that you could, you know, leave the office, get home, get your family settled. Us in the Toronto office would carry on because that was a night and day file, as you would remember, it went on. And then Milly and I would have some time off when you came back online, and we sorted it all out together. 

I think that one of the important things for the three of us has been, you know, an understanding of the juggling that we are doing and the ability to complain a little bit to each other from time to time. In a feeling that our complaining is completely, completely safe. But I also say that we all three have what I say is in the Blakes restructuring group DNA. We just all wanted to be the best that we could be as restructuring lawyers. We all wanted really to lean in on, not just the practice but the policy, the development of the practice, the industry organizations. So, we were, you know, all committed to the same goals. And as a result of that, it was very easy to all work together and to find ways to help each other and understand that those goals of being the best often run into other things that you’re doing in life, and there is a balance that has to be struck. So, it was that understanding I think amongst us and our common goal of what we were doing for the Blakes practice that really, really helped us along the way. And although I am older than my colleagues, I delayed having children for some time. I had two stepchildren, but then my daughter was born the same time, Milly, as your first child. I remember getting together when we were both on mat leave. So, I had my first child at 38, and I adopted at 41. And so, I had young children all through the same phase that you guys did, even though I was older. So, we were also learning a little bit together as we went.

Milly: It’s been incredibly meaningful to work alongside Pam and Kelly. We all have very demanding lives, both at the office and at home. We’re crisis managers in our careers, but we aren’t robots. We are human, and it is really a special comfort to know that you’re not alone, that others have gone through the same or similar challenges and self-doubts, you know, lack of sleep, concerns that you are not good enough, good enough mother, good enough lawyer, good enough spouse, all of that. And I’m not downplaying men, they have their own unique challenges, of course, but for women, it’s just different. And almost every professional woman knows it and feels it on a daily basis. And so, while some people look to get affirmation and kinship through others in their particular firm or even outside the firm or company itself, we have the unique advantage of having that all within our practice group, so I think that’s very special and unique.

Jenna: Thanks, Milly, that’s very well said, and something that certainly brought me back to Blakes. For those of us earlier in our careers and for listeners aspiring to paths like yours, what is one piece of advice you would offer, perhaps the advice you’d give to your younger self. Milly, would you like to start?

Milly: Law is a business, and being a good and smart lawyer is just not enough. You need to invest in business development. You need to start young and not as a senior associate. You need to treat it as a file and give it attention and build a strategy. And yes, sometimes there seems to be not enough hours in the day to do your work and have time for your family. But you know, we talked earlier about work-life balance and prioritizing. And some days, business development needs to take a priority, and it needs to be one of those balls that you’re juggling in the air, and sometimes that ball needs to take priority.

Pamela: I think from my perspective, it’s not second-guessing yourself. Second-guessing yourself causes a lot of anxiety, and it’s something that we all do, of course. We’re not immune from it. But, I think that sometimes women are a little bit more prone to reflecting on whether they performed as well as they could have in a meeting or they gave all the best submissions they could in court or whether they interjected at the right time, whether they did the right thing. I think that telling my younger self, “Don’t sweat so much and don’t second-guess what has happened. You were on track. You knew what you were doing. You gave good advice.” Don’t second-guess, because that does take a lot of energy.

Kelly: Those were both super thoughtful. And I agree, I agree with both of those. I think that’s great advice. The other one I would maybe pick up on is to be your own cheerleader. I think women are less likely to talk about themselves and their successes a lot of the time or to downplay their successes. And it works against us, I think. So, I look at it, and I say, I am at this firm. I am working with these people, and I am on these files, and these clients have engaged me because they know that I have value and I bring value to their files. And I just need to remind myself of that. And I think that’s something that I go through life with a little bit of imposter syndrome. So, that’s why I think nipping that in the bud earlier would be better.

Jenna: That is such fantastic advice for all lawyers, or any professionals, really, but especially for women. Thank you for sharing that.

Pamela: Jenna, on behalf of all three of us, thank you for leading us through this engaging discussion today and an opportunity for us to reflect on our careers and how important this practice is and the development of the practice and the role of women in this practice. And certainly, something that I appreciate very much is to be able to work with you and the emerging talent that we have in our group. And of course, the next, next generation of women that are pursuing this practice and with excellence and enthusiasm. So, thank you, Jenna.

Jenna: Thank you, Pam, that’s very kind. I’m very grateful to be a part of the group that the three of you are all continuing to mentor and support.

Well, of course, a big thank you to all three of you, Pam, Kelly and Milly, for sharing your experiences, insights and advice with us today. To our listeners, thank you for tuning in. We hope you found some meaningful takeaways from today’s discussion. 

Until next time, take care.

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