• Laura Hay, Leadership |

I’ve always felt that it is as important to speak about successes as it is to openly discuss failures and lessons learned. For me, it is the collective, these balanced experiences we all have, that make us who we are today and in the future. Understanding the important role that failure plays in our development is core to our future successes both at work and outside work.

That is exactly why I enjoyed my conversation with Judy Dinn, Executive Vice President and Chief Information Officer at TD Bank, America’s Most Convenient Bank®, and her absolute comfort in speaking with me about how learning from failure, taking risks, and pursuing your passions are key to finding the career and company that’s right for you.

I had many takeaways from my conversation with Judy. Below are three highlights that I feel will be helpful to all women in their careers.

Frank talk about learning from mistakes

Judy's career is marked by continuous success—leading technology organizations at several powerhouse U.S. and Canadian banks, attaining academic milestones, and juggling dynamic hobbies like being a yoga instructor and certified nutritionist.

So, imagine my surprise when Judy chuckled and confessed, “Oh Laura, I fail every day, including today. I may say the wrong thing at times or may not motivate people the right way, and in technology, it's rare that things go perfectly—yet we still hold the bar high.”

Judy expressed that the fear of failure has to be right-sized, and we have to realize that failures are not only how we learn and improve—from the moment we start learning to walk—but also something everyone experiences.

To make her point, Judy reminded me how a standard, and perhaps the most insightful, question that interviewers pose to prospective hires is, “Describe a past failure.”

“They aren’t looking for candidates who say, ‘I have never failed,’” says Judy. “They want to learn what risks you’ve taken, what you learned from your mistakes, and if you're self-aware. They want to know what you did after making a mistake and if you took accountability for it.”

Getting comfortable with taking risks

For many, it's the fear of failure that causes us to also fear taking risks, both personally and professionally.

Being comfortable with taking risks can definitely help women rise into leadership roles. Judy advises that senior management looks for individuals who are willing to take risks. "Leaders are the ones who take us into the future," she says. "But at the end of the day, there isn't a roadmap for much of what we do, and leaders are making decisions based on research, experience, and the information available to them. Learning to take educated risks, which can be uncomfortable at first, is important if you're looking to reach a leadership position.”

Taking risks leads to finding the career path that's right for you

Perhaps the most important result of risk-taking, though, is how it can help you learn more about yourself and find the path that's best for you.

In Judy’s case, an emotional intelligence course she took years ago played an important role in helping her learn more about herself: “It was an amazing opportunity to identify and understand my own strengths and weaknesses. And it was important, because if you don’t know those things, you can't effectively lead people or be most effective at helping your organization move forward.”

She also credits her career strategy of moving around a lot with helping her to identify what's important to her. Change can feel risky, but Judy explains, "Experiencing different companies and different types of managers can help you discover your likes and dislikes so you can shape your career on terms that work for you. For me, it's important to be able to be myself and to do what I am passionate about amongst people who are supportive."

Having that self-awareness has helped Judy make the career decisions that were best for her, including leaving jobs where she didn't feel she could be her authentic self. "It's important to land somewhere where the culture is a good fit, utilizes your strengths, and provides a safe space for you to grow."

Judy’s final words really stuck with me: “We can spend a lot of energy being something that we are not, and all that energy could be better served put towards what you like to do and with the people who support you.”

My conversation with Judy really made me think about my own relationship with risk and failure, and in doing so, I certainly learned more about myself. I encourage you to think about how you approach risk-taking and if perhaps you have room to grow in this area. If you're thoughtful about the risks you take, they may lead you to a terrific place.

More about Judy Dinn: With more than 25 years of experience in technology and financial services, Judy has held the post of Executive Vice President and Chief Information Officer at TD Bank, America's Most Convenient Bank, a member of TD Bank Group, since late 2021. Judy first joined TD Bank Group in 2020 as Chief Architect and CIO for U.S. Cards. Previously, she was CIO, Credit Cards Technology, at JPMorgan Chase. Judy also held senior roles with various admired companies, including Royal Bank of Canada, global payments provider D+H, CIBC, and Siebel Systems. Judy initiated her career at Deloitte Canada as Consulting Manager, IT Strategy, ERP & CRM Specialist. She earned an Honours Bachelor of Mathematics (Computer Science with Business and Mathematics option) at the University of Waterloo and completed advanced business studies at the Ivey Business School at Western University and Queen’s University at Kingston.

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