In conversation with Stephen Aylward
In conjunction with the Toronto Lawyers’ Association Emerging Excellence Award of Distinction presentation in Toronto on May 10th, Evan Thompson spoke with Stephen Aylward , Barrister and Solicitor at Stockwoods LLP , Toronto. and this year’s Award recipient.
TLA: What attracted you to the legal profession?
Stephen Aylward: I come from a family of lawyers – my grandfather was a lawyer and a judge and my father is a lawyer. I really had no choice but to become a lawyer to keep up with the dinner conversation .
To prepare myself for law school , I debated during undergrad . The majority of my friends from debating went to law school , as well .
TLA: Can you share some of the recognitions you received that brought you great satisfaction?
Stephen Aylward: The positive outcome of the Sharma case * is without a doubt the highlight of my career to date. This was a passion project for me as it united my professional and personal views on the matter of equality rights. Many people doubted our chances of success at the Court of Appeal but we had some lucky breaks with the development of the law regarding Section 15 Equality Rights, which benefited our case and client. It’s still a case in progress.
Generally, I always love reaching a settlement for my client when an outcome is reached that both sides can live with. It’s a challenging exercise but very rewarding when it works out.
TLA: Can you share some moments that tested your resolve to become (and remain) a litigation lawyer?
Stephen Aylward: Every decision that doesn’t go your way , especially when you feel you are right and the judge or panel of judges come to another decision. It can be frustrating and you may find yourself questioning your judgement. Having the skill to set priorities and when to argue and when to step back is a skill that comes with experience.
I have never reached a point where I doubted my commitment to the profession.
So far , it’s worked out but some of the challenges have been daunting.
There is a lot to learn in terms of trial advocacy and trial strategy and to differentiate between the losses that you can control and those you can’t control. There’s no point in beating yourself up about the latter.
TLA: What makes a good lawyer?
Stephen Aylward: Soft skills are essential. A sense of judgment and knowing what’s important to driving outcomes is also very valuable . It’s a difficult skill to develop and one that can only come from experience. Learning from lawyers who show good judgement is essential. Understanding the human side of the law using emotional intelligence and analytical skills is also important , which means k nowing when to argue the law and when to argue the facts. I am pretty even keeled and this helps in high conflict situations where I can bring a calm presence. When it comes to legal writing and all forms of communication, I have always liked the adage “think like a lawyer - write like a human.”
TLA: Can you talk about some personal volunteer projects outside your law practice.
Stephen Aylward: I have been heavily involved with Fighting Blindness Canada, Canada’s largest vision research charity, as a member of its Board. This is deeply personal volunteer work for me, as I have experienced vision loss throughout my life and am legally blind. My disability does not hold me back and it’s driven me to demonstrate that I can perform at the highest level within my profession.
Living with a disability gives you a real sense of perspective. It teaches you the difference between everyday annoyances and real struggles. It teaches you patience, to be forgiving of yourself and others.
I have become a mentor, advocate, and trailblazer for people with vision loss.
Law can be all consuming. I could spend most of my time puzzling through my cases, but appreciate the need to step back. My hobbies include playing Irish fiddle tunes with friends each Sunday afternoon (including CBC’s “Q” host Tom Power who is one of my oldest and closest friends from back home in Newfoundland). It helps me clear my mind for the week ahead.
TLA: How has social media affected the legal profession?
Stephen Aylward: Law is not about black and white. It is about compromise and finding nuance s in huma n interaction , rather then seeing on e side as right and another wrong. Social media can be extremely polarizing and can silence moderate voices that are overcome by louder ones . On the positive side, s ocial media helps me keep up with the legal world on a daily basis and it’s been a life saver for me through pandemic as I can stay connected with the legal community. It’s not as much fun as going to a party but it keeps you in touch with the community.
TLA: Do you have any advice for aspiring litigation lawyers about how to navigate their journey?
Stephen Aylward: If you are not sure about going to law school, first ask yourself what you want from it. It’s not a career to enter by default.
Some people choose law for the wrong reason s . It’s a g ood way to make a living – we work indoors and in largely hazard - free environments – but it can be draining. The key is to be able to enjoy the process, like w riting a well-crafted letter . It also helps to be able to find the humour in a tense situation. Keeping an a ppropriate sense of humour keeps me going and helps me better understand the human condition an d what makes people tick. Metaphors can be very powerful and I use them in my arguments as much as possible .
In one case, the other side quickly adopted a metaphor I was using about an iceberg and what may lie below the tip of the iceberg . I lost the case but claimed an advocate’s victory for convincing the other side to buy into my framing. I haven’t retired that metaphor, by the way .
TLA: Who are some people who have helped guide you in your career?
Stephen Aylward: My gr andfather, Fintan Aylward , went to Dalhousie University to study law . Coming from a poor community on the Burin P eninsula in Newfoundland, h e pulled himself up by the bootstraps , as he also worked to send money home. As a result, he never took anything for granted and he passed this philosophy on to me.
He became a judge but really remained a lawyer at heart and always said he loved “ a good jeezily racket.” We had some great times together.
Many of my closes t friends are lawyers and some of the best laughs and most difficult conversations occur when we discuss legal victories and defeats. We have a role to play in society in maintaining the rule of law and respect for the administration of justice in defending those values in an uncertain world.
The Honourable Thomas Cromwell guided me when I spent a very formative year as a clerk at the Supreme Court of Canada. (He asks me to call him “Tom” now but I still find that impossible to do). He took the weight of the office very seriously while remaining warm and generous as a mentor and a boss. He was a great role model for me in my first rea l full-time legal “job” and set me on the right path.
* In R. v. Sharma, Steve acted as co-counsel for a young Indigenous woman in the Court of Appeal for Ontario, successfully challenging the constitutionality of a law restricting the use of conditional sentences. This case single-handedly implemented one of the Truth and Reconciliation Commission’s Calls to Action. At the time of writing, Steve continued to represent Ms. Sharma as Canada appealed this decision to the Supreme Court of Canada.