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By: Orit Sinai and Jonathan Cullen

We all sometimes wish we could back in time. As legal professionals learn from their mistakes, they think “I wish I knew that earlier.” What would you tell your younger self if you had the chance?

That’s the question that Jonathan Cullen and I asked some of the most accomplished attorneys in Canada. The result is a basket of advice that shows young lawyers the diversity of pathways to success in law and practical tips.

Coming into 2020, none of us could have expected the chaos and disruption which ensued. Now is an ideal moment to evaluate past choices and use that knowledge to shape the future.

The stories told here offer different illustrations of what both the journey and the destination of a lawyer’s professional life can be.  Perhaps one of the most important pieces of advice to a younger self would be to constantly recognize the potential you have – and not limit that needlessly. Hopefully, they will help you to write your own.


Luckily the advice I would give my first-year self I actually got in my articling year, but I find myself often reminding myself or others of it. In response to “what do the partners/my boss/leadership think of me?” the reality is so often that they are not thinking about you. Lawyers are often not great at giving feedback and generally no news is good news. Work hard and focus on the feedback you do get – mark-ups of your drafts, corrections or clarifications on your client emails or calls, etc. Watch other lawyers in action whenever you can and learn what to do and often what not to do! Develop a style that works and is authentic to you. Try to review your own work and interactions with a critical eye to give yourself feedback. Perhaps most importantly, when you get to a point where you are working with more junior lawyers do not continue the cycle! Be intentional and generous with your feedback – both good (praise publicly) and bad (constructive criticism privately).

–  Erin Zipes Vice President, Assistant General Counsel – Shopify

Focus on building  and maintaining relationships with peers outside of the practice of law. Don’t lose sight of friends from your life prior to law school. Friends from high school, your undergraduate degree or from your hobbies or interests outside of law are a great asset to cultivate and grow as you develop in your career. For a lawyer in private practice, those peers will be a source of perspective and organic client development that will help pave the way towards a strong client portfolio as you mature into a partner. 

Christelle Gedeon, Chief Legal Officer -Aphria inc

Develop expertise in legal areas and subject matters that you have an interest in, but that are also likely to grow/evolve as you progress in your career (for example, privacy/information security law, legal aspects of artificial intelligence, etc.). Begin networking and cultivating relationships from your first year of practice – speak at/attend conferences, write articles, stay connected to your law school friends and classmates, seek out mentors at your place of work (and beyond). It’s easy to spend the first few years of practice fixated on your current job/role and just getting through the days (especially if you’re at a Bay street firm) – remind yourself that there is more out there! Just because you’re a lawyer doesn’t mean you have to spend your entire career practicing law (or even exclusively practicing law) – for example, if you do work in-house for a company, you can always transition to a ‘business role’ if that’s where you determine your interest lies. It’s not a big deal if you don’t know the answer to a question (you’re only a first year, after all); but it’s likely not that hard to find out the answer, it may just take some time and effort – do it! I suppose the one other thing I would remind my first-year self is that so much of success is luck / out of your control.

Tariq H. Remtulla, Regional Counsel, Canada at Airbnb

Have confidence in yourself but don’t be afraid to ask questions. In fact, never stop asking questions – you will keep learning from the answers! No matter how busy things get, do your best to stay in touch with people. It’s never too late to reconnect with an old colleague, classmate, acquaintance etc. You never know how your paths may cross again!

-Jennifer Sernaker-Tytel, General Counsel and Corporate Secretary, Toys “R” Us Canada

Advice I would give my first year old self: Get a mentor and preferably a sponsor as early on as possible in your career and ideally in your first year of practice. The first few years of practice can be so tough and so many great lawyers leave Bay Street too early because of the grind. A mentor can help you get your bearings in your first year(s) and hopefully give you the support you need to dedicate yourself to private practice for at least 4-5 years. Having a few solid years of Bay Street experience from one of the top tier law firms will pave the way for a more successful career with varied options for career paths.

– Carole Dagher, VP, Legal at Loblaw Companies Limited

“Do as many different types of work as you can and resist the urge to specialize too early. Being exposed to a variety of industries, practitioners and perspectives will all shape who you become, both personally and professionally. And never say you can’t do something….just surround yourself with people who can, until you become one of them.”

Jennifer D. Suess, Senior Vice President, General Counsel & Corporate Secretary RioCan REIT

“My best advice would be to try to get involved in as many different files that you can. The one thing in private practice is that you specialize incredibly quickly. Getting exposure to a variety of files will allow you to gain a wide breadth of experience; which will benefit you if you want to end up in a in-house role. I certainly bounced around, and got involved in securities, M&A, Lending, IP work and it helped me tremendously. Try to get exposure to as many different files that you can in your first year. Of course, you need to eventually specialize – but the longer you stay in private practice, the more specialized you become and the more difficult it may be to exit. I feel private practice at the three year mark, which I think is the perfect time. I do believe that leaving private practice during your 5th/6th year is a bit too late, as you are too specialized. Try to exit at the 3rd year mark, if your goal is to go in-house.” 

– Philippe Savard,  Vice President, General Counsel and Corporate Secretary at Acerus Pharma

Calm down. Relax. Don’t panic. You can do this…if you calm down, relax and don’t panic.

Being a lawyer is hard and takes a lot of thought and hard work. The more you can slow down and think and take the time to “figure it out”, the better your work will be. And while what we do is important to be sure, no one will die if we aren’t perfect. Don’t forget that. And, please, go home. You need family time and sleep. There will always be more work than you can finish…go home.

– Matt Gottlieb, Managing Partner Lax O’Sullivan Lisus Gottlieb LLP

Value spending some time on the other side of the area in which you practice. In many areas, there is a regulator of some form. To the extent you can spend time with the regulator is extremely useful in developing a practice and developing credibility with them. It’s remarkable, I can still pick up the phone in departments that I used to work closely with and they will answer.

Don’t be afraid of change. It can have a very positive impact. In context of developing a career, round out your experience to best serve clients. If you can get some form of in-house experience if private practice is your long-term goal, being inside a client for 6 months or a year provides tremendous insight into long term development.

Financial acumen is a very important aspect to being a lawyer – whether you’re a family lawyer, or even a criminal lawyer. Fear of basic numbers is something lawyers need to get over and get financial training.

Have a collaborative work style. One thing that gets in the way of lawyer success is a little bit of arrogance. Serving clients is what it is about. I view law as a social science. Trying to solve social problems.  Law, corporate organizations, criminal law, it’s about people. I can relate to people. It’s not just about the case. You need to really have a relationship with your client. I’ve refined my people skills.  You need to do the work and think hard, but to differentiate is to understand that human element of the law.  If you’re aware of it and it’s part of how you perceive the world, and watch other lawyers who are successful, decide who you want to model yourself after. Through observing the kind of people you want to emulate.

– David Allgood Former General Counsel RBC

“My advice to my first-year self would be to start defining your brand early on in your legal practice. Go into first year with a clear idea of what specific area of law you want to practice, even if you change later. This will project a sense of focus and will attract more senior lawyers to you. Opportunities open up when senior lawyers associate you with a particular practice area or interest; it will distinguish you from your other first year colleagues. I would also start out by aggressively building my internal and external network through industry or legal associations. It’s always helpful to know and be known.”

Carole Piovesan Co-Founder & Partner INQ Data Law

This is what I know, and in some cases lived by during my career at Deloitte:

  • Serve- the company, the team and society.
  • Be humble – the role is a big and important one.  Don’t let it go to your head.
  • Build diverse teams and create a work environment of inclusion.
  • Live and work with no regret – being successful (as the General Counsel, as a parent, and in your other roles) means sacrifice. Be deliberate in your choice so that you have no regrets in what ‘has to give’.
  • Delegate, but be present and available.
  • Know your value.
  • Listen and speak last.
  • Say ‘yes’ and take risk. 
-Kenneth Freeden General Counsel Emeritus & Senior Partner Deloitte Canada

With your most transformative of ideas, those that represent your vision, do two things. First, be flexible: learn from the experience of others, turn harsh criticism into an opportunity to make your idea stronger and actively seek out feedback.  Second, be bold: don’t give up, be patient, and see the long game. Crazy ideas are the ones that change the world. 

– Jonathan Cullen

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