Skip to main content

Seizing Opportunities for Successful Career Transitions

Constellation Software board member Claire Kennedy shares her advice about building confidence, setting goals, and rising into leadership roles 

Claire Kennedy has mastered the art of getting comfortable with stepping out of her comfort zone. Her ability to successfully make career transitions has opened doors and paved the way for her many accomplishments.

After first pursuing an education in chemical engineering, she pivoted to a career in law. After several decades in the business world, she is now a Senior Advisor of Clients and Industries at Bennett Jones LLP, a top Canadian business law firm. In addition to her work giving legal advice to businesses, she has expanded her knowledge by becoming well-versed in the world of public and private boards and pursuing ongoing education. 

Constellation Software’s board welcomed her as a non-executive director in 2022, where she helps provide oversight to management on behalf of shareholders. “Outside board members bring an ability to probe things or consider things from outside the company, and offer good judgment and an independent perspective,” she says of her role.

Constellation is definitely one of the most data-driven organizations I have ever encountered. What really stands out for me is the accountability and the decentralized nature of management practices. It's very different from other organizations. What I think Constellation Software has done so well is they've really honed the craft of M&A.

-Claire Kennedy, board member, Constellation Software

Other boards have also benefited from her leadership, including the Bank of Canada where she serves as a Lead Director, and publicly traded companies Alamos Gold and Neo Performance Materials. She served on the University of Toronto’s Governing Council from 2012-2021, including four years as Chair. Currently, she is part of the Dean’s Advisory Board at the Rotman School of Management. 
She shared her lessons learned with readers of Acquired Knowledge magazine about how to grow your knowledge, network, and experience, wherever you may be starting from.

You've achieved success in so many parts of your career and made several successful transitions. When you enter an unfamiliar situation, how do you build confidence and earn respect from others?

Confidence is a bit like a workout. I can think about squats all day long, and my legs will not get any stronger. I think it's like a muscle that you build over time, and you can't develop it in the abstract. Take opportunities where you push yourself a bit outside of your comfort zone.

If you come into an unfamiliar situation with a genuine curiosity about things, it impacts the way people interact with you. One of the most effective directors I've seen approaches a conversation – and it might not even be the easiest conversation – by saying, “I'm curious about…” and then he lets the person he’s speaking to open up. 

I think that phrase is really a powerful one, because it's very neutral. You're not saying you agree or you disagree. It's neither hostile nor appeasing. It allows you to draw out more facts and impressions that are really important for good decision-making.

Claire Kennedy received an honorary degree from the University of Toronto in June 2023. (Photo by Steve Frost/U of T)

When you were studying law, a professor gave you a piece of advice. Can you tell us why it stays with you to this day?

When I took my criminal law course years ago, I had a great professor, Allan Manson, who said, “It's not about truth, it's about proof.” It has an obvious application in criminal law, where we hold a standard of the defendant not being guilty until the government has proven its case beyond a reasonable doubt. My interpretation of that, when applied outside of law, is that it's not enough to be right – one has to be persuasive. 

I come from an engineering background where there’s often an attitude of “There's the proof” or “There are the facts.” And then the expectation is that people will go forth and do what you expect them to do based on these facts. But human beings are just not like that. 

Certainly, it helps to be right, but I think it's a mistake to conclude that because one feels one is right, it will somehow motivate others to do what you want them to do with the information that you present. In fact, done the wrong way, it can actually generate resistance. 

People generally don't like to be told what to do. Instead, it is helpful to frame things in a way that allows you to be persuasive, which is a lot more about listening than it is about talking.

What can organizations like ours do to empower emerging leaders?

Give people opportunities. You may find that some people in your organization need more encouragement to take those opportunities than you think they ought to need. So encourage them and give them multiple opportunities.

Part of it, though, is that you have to be prepared to seize those opportunities. If you are being encouraged to take on a new leadership role, it can often be the case that you want to feel more ready than you need to be before you're willing to take something on. While it’s important to do your homework and to be prepared, you have a responsibility when guiding your own career to seize those opportunities and use them to learn. 

What has been the role of volunteer work in shaping your learning and career growth?

One thing that I found was super helpful to me is I did quite a lot of volunteer work at Universtiy of Toronto, culminating in being on the Governing Council, which is like the board of directors of U of T. There are 50 people on that board, so you have to learn to be a leader in that environment. 

When I started, it was pretty low-stakes volunteering. I was on a committee, I put my hand up. Then you learn to chair a meeting. And the next thing you know, you're an emcee at an awards night. It means the next time I'm in front of a podium, in a different context, it's not my first time and it feels easier. 

It comes back to my belief that this is an apprenticeship, you’ve got to learn by doing. You cannot think your way into success in that environment. Create those opportunities or find them for yourself.

Stepping outside your comfort zone is absolutely a requirement for growth, period.

-Claire Kennedy, board member, Constellation Software

What’s the value of self-reflection in your life?

Self-reflection and understanding yourself are really important. For the majority of my life, I didn’t think keeping a journal was important. Now, I have one. There's a school of thought that says you don't have an idea unless you've written it down. It's too ephemeral otherwise. So, my journal is where I try to make things more concrete.

Self-reflection allows you to step outside yourself a little bit and see yourself as a participant in a particular scene, and therefore allows you to control how you react.

What advice can you share about setting career goals?

I think you need to have a long focal length and a short focal length at the same time. Have goals and ambitions, but be prepared to lead your intentions. What I mean by that is developing what I call sound habits of mind and body. The big goal is that long focal length, and leading your intentions is probably a shorter focal length. You need to do both.

You’re a believer in the power of strong habits to help achieve goals. How do you make this work for you?

What I find works for me is creating structure in my life. And the goals then almost take care of themselves. You set yourself up for success. I have these little routines that I do, not unfailingly, but when I do them, I'm much better and more capable in a professional context. They create an environment in which it's easy to do the right thing. 

For example, I get up and go for a walk every morning with my friend. We have done that essentially every day for over 20 years. I keep my walking clothes at the bottom of the bed so I can get dressed in the dark. Unless I have literally pulled an all-nighter, I have more energy if I go for a walk than if I sleep in. 

That’s a good example. Do you have any thoughts on how leaders can stay focused when they may be facing so many demands?

I wouldn't overlook the importance of what I would call micro-structure in your life, whether it's exercise, nutrition, journaling, how you manage technology, or how you deal with distraction. We're just inundated with distractions now. And I think that's one of the hardest things that we have to do, is manage our minds and our attention.

Constellation Software President Mark Leonard talks about making decisions around time, energy, and attention – where are you spending them? Those decisions add up to the ability to then execute the larger things that you want. You will be much less successful with the larger things until you've mastered the smaller things.

A good habit that we encourage throughout Volaris is to constantly work on expanding your network - something you have also practiced. What’s your advice for how to network strategically?

I think the key to successful networking is curiosity and generosity. If you have those, I think you will be a good networker. What do I mean by that? Don't ask what your network can do for you, ask what you can do for your network. 

Connect two people across your network, be a synapse. Usually, I’ll set it up in advance, I don't give a cold call introduction. Let them know that you think it would be a fruitful connection and ask if you can go ahead and make the intro. And 99 times out of 100, they’ll say yes. If something positive comes out of it, now you've got two people who are well-disposed towards you. 

Constantly think about what you can put into your network. Don't worry about taking out – those opportunities will come. Also, don't think that you've got to give your elevator pitch. Just ask open-ended questions, people love to talk about themselves. Follow the thread, wherever they lead you. Eventually, they'll come around asking you some questions. You'll learn something in the process, and then be prepared to move away and continue to mingle. 

You’ve also got to conserve your energy. Ask yourself: “Is this going to advance the kind of contacts and grow the network that I will benefit from, and that I’ll be able to contribute to?” If the answer is no, or it's not as good as this other opportunity, then don't do that and do this. You get to calculate an expected ROI from your effort, so do it.

Claire Kennedy’s trip to Antarctica in 2016

In your free time, you volunteer for True Patriot Love Foundation, a Canadian charity that supports military veterans. And you took a trip a few years ago to Antarctica in support of mental health for veterans. I understand that trip was very impactful to you. Can you tell us more about that?

Yes, it was in January 2016. If you ask me why I did that, I still don't have a good answer. Maybe it was the benefit of not really knowing what I was getting into. The time on the mountain was the hardest ten consecutive days of my life – and I say that as a single mother of two teenagers. 

In spite of how difficult it was – but honestly, because of it – it was one of the best things I have ever done. It was such a powerful experience. We climbed Mount Vinson, which is one of the Seven Summits, so it's the highest peak on the continent. You get dropped off by plane at base camp, go to low camp, climb a headwall up to high camp, and then go to the summit. The headwall is the steepest part of the ascent; you’re basically going up for ten hours. We had no Sherpas, so we had to carry everything on our backs. It was exhausting.

That sounds like quite the challenging climb. How did you find the strength to get through it?

For hours, I said to myself, “Kennedy, you only have one thing to do in the rest of your life – you just have to move your foot. You just have to take one step.” That was how short my focal length was. It wasn't even thinking that I had to get to the top of the mountain. 

That was a real lesson to me in terms of the ability to focus, and how sometimes you have to bring that focal length right down. One of the soldiers said to me, “Slow is smooth, and smooth is fast.” And it worked like magic — to do things once and do them right. 

In my professional life, there have been manifestations of that. Oftentimes, you actually have to slow down to speed up. And the time that you have to do that is when you're most frazzled or busy or overwhelmed. That's when you have to step back and tackle things — one at a time, in a very deliberate way.

Read more: