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Twenty women in top leadership roles share their biggest lessons: Celebrating 20 years of The Judy Project at the Rotman School

March 6, 2023

For two decades, Judy Elder’s ambitious spirit has lived on at the Rotman School of Management through a program inspired by her legacy: The Judy Project.

Hosted by Rotman’s Initiative for Women in Business, The Judy Project is one of Canada’s leading executive forums, uniquely designed to support and prepare women who are ascending into executive leadership and C-suite positions.

Before her death in 2002, Elder was — among many things — an executive at Microsoft Canada, a dynamic visionary and a respected Canadian business leader. Throughout her career, she urged women to be proud of their ambition, to reject barriers and to simply "make stuff happen.”

To celebrate the 20th anniversary of The Judy Project and to mark International Women’s Day, we’re sharing a list of timeless leadership lessons from 20 women who have been involved in the program over the years.

These insights are adapted from the book, The Collective Wisdom of High-Performing Women, a collection of advice from more than 70 women who have participated in The Judy Project since 2003.

Judy Elder

“If you acknowledge the importance and power of your ambition, recognize that it is there to drive you to greater achievements and sustain you through the challenges. And if you couple it with competence, hard work, and the morality you learned at your mother’s knee, you can defeat the insidious erosion of feeling inadequate, the fear of being in charge, the doubts that we all have about our capacity to lead.”

Judy Elder, during her speech for the Women’s Television Network’s Gift of Wisdom series on March 7, 2002 (the speech in its entirety can be found in this book)


“While careers can start out by balancing your emotional quotient, your curiosity and your intelligence, over time the intelligence piece isn’t the differentiator. EQ and curiosity become the differentiators for leaders — how you relate to people; how you communicate, solve problems and help those on your team be better and do better than they thought possible.”

Linda MacKay, Senior Vice President, Personal Banking, Distribution and Strategy, TD Bank on “Lessons Learned”


“I foster an environment that engages and embraces the whole person, including the personal. As the founder and CEO, I must set the tone by living this value in plain sight for all to see. I’m a mother of three, and when I leave to attend a school event for my daughter, I tell everyone where I’m going, how long I’ll be out of touch and when I’ll be back. We have to be ourselves, unafraid of judgement and yet accountable.”

Lorna Borenstein, Founder & CEO, Grokker on “Give Up the White Lie”


“Here’s the thing: If you don’t ask, you don’t get. And by all means, you should ask for what you want. Women tend to think business is a meritocracy. Do a great job and the raise will come. But life isn’t fair. The person who puts up their hand for the raise they want, and makes the case for why they deserve it, will get more than you.”

Nancy Vonk, Co-Founder, Swim on “How to Ask for a Raise”


“The advice I share with young women today is honest and straightforward: There is no ‘all’; there’s no such thing as ‘work-life balance.’ Instead, I say that it’s about your all and how you find your own version of work-life integration.”

Kathleen Taylor, Chair of the Board, RBC on “How to Integrate Your Work with Your Life”


“Without a clear understanding of your values as an individual and a leader, you won’t be able to make the right decisions... You can respectfully but sincerely challenge authority — especially if you’re in the right.”

Jennifer Gillivan, President & CEO, IWK Foundation on “A Lesson in Courage I Learned from My Grandmother”


“Be authentic with your boss and have a heart-to-heart conversation with them about your maternity leave plans. As awkward as it may be, especially with a male boss, try to open up and share — and know that this isn’t just a personal discussion, it’s a professional discussion.”

Tina Lee, CEO, T&T Supermarkets on “Being Authentic as Moms-to-Be"


“You have to be honest and upfront, and not assume that others will be aware of your career aspirations. I learned that if I don’t make my goals and interest known, how can I expect anyone else to know them?”

Cheryl Brunato, Vice President, Xplornet Communications on “Make Your Aspirations Known”


“The job of business leaders in these complex and unstable environments is to create the conditions for others to come up with new ideas, to push forward creative ways to think about business problems and to help lead others in collective endeavours.”

Tiziana Casciaro, Professor of Organizational Behaviour and HR Management, Rotman School of Management


“When I was deciding to make the transition back to academia, my mother was fiercely on my side. We’d talk on the phone, and although I knew it was possible to have a career and children, she always reinforced that perspective. She had this wisdom that kids are small for just a short time and that life gets easier after five or six years, when they start school. Her outlook matched mine: ‘Don’t give up your career just to make it easier right now’.”

Beatrix Dart, Founder and Executive Director, Initiative for Women in Business; Professor of Strategic Management, Rotman School of Management on “From Consulting Back to Academia”


“We need people to support us, to work with us to achieve common goals. That can be done effectively only if we genuinely care about them, and if we show we care through our words and our actions.”

Sandra Rondzik Popik, Vice President Human Resources Technology Infrastructure & Innovation, CIBC on “Making it Personal”


“Although it’s important to see more women achieve C-suite positions and to serve on boards, it’s also extremely important to help women earlier.”

Colleen Sidford, Board Director, Invesco Canada; North American Electric Reliability Corporation; CBRE Caledon on “Don’t Wait to Boost Women”


“My upbringing emphasized not being the centre of attention, but rather suppressing oneself and being one with the crowd. This belief became especially important to overcome as I assumed leadership roles, because you need to articulate your vision in compelling and passionate ways to inspire people and bring them along the journey.”

Rowena Chan, Senior Vice President, Sun Life Financial on “How My Sponsor Pushed Me Into the Spotlight”


“We often talk about how to manage business risk, but we don’t often reflect deeply on professional risk — a very personal decision. People who are looking to “reinvent” think it’s risky. I would argue that to not take a calculated risk is the biggest risk.”

Heather Fraser, Founder & CEO, Vuka Works on “How Do You Manage Risk?”


“Leadership is a journey that challenges, invigorates and fulfills. It exhausts, advances and enlightens. If you get the opportunity to go through this yourself, you’ll know how it feels to be at the bottom reach of your internal resources — and how just pushing through can be most liberating.”

Kim Mason, Senior Vice President & Head of Private Banking Canada, RBC Wealth Management on “Pulling Up Roots — to Grow”


“The ability to make a decision quickly and confidently is a trait I appreciate in other leaders, and it has helped me succeed and grow as a manager and leader. I’ve had to make many decisions — sometimes difficult and unpopular ones — but I don’t hesitate to voice my opinion and decide.”

Jane Russell, former Executive Vice President, TD Bank on “A Letter to My Daughter”


“I knew that being uncomfortable meant that I was growing and learning. It was challenging. I had to dig deep at times. But being focused and tenacious on overcoming one challenge at a time — along with some very supportive colleagues — helped me to be successful.”

Helena Gottschling, former Chief Human Resources Officer, RBC on “New City, New Role”


“I try never to allow a fear of failure to hold me back from trying something new, or from following an ambition that others question.”

Shari Walczak, Co-Founder and Chief Strategy Officer, The Garden North America on “Stepping Out of a Big Job to Launch a New Venture”


“You don’t need to be a man to be successful. And you don’t need to be aggressive to be successful. You need to be yourself. If that means being honest and kind, then the world will be a better place.”

Sarah Davis, former President, Loblaw Companies Limited on “How Authenticity Can Lead to Success”


“Seek out assignments that will differentiate you, challenge and energize you, and gain you recognition for leadership capacity. This in turn will build your confidence, which is an imperative.”

Dale Ponder, former Co-Chair, Osler, Hoskin & Harcourt LLP on “Navigating in a Male-Dominated Industry”


The full version of their insights and more can be found in the book, The Collective Wisdom of High-Performing Women, which offers advice for women about advancing their careers while remaining true to themselves. The book was edited by Colleen Moorehead, who has served as the business director of The Judy Project since its inception in 2003.

Written by Jessie Park

The Collective Wisdom of High-Performing Women -- book cover

The Collective Wisdom of
High-Performing Women:
Leadership Lessons from the Judy Project

Available now from Indigo and Amazon.