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Colleen Moorehead's advice for women: Put your hand in the air and take risky assignments

"Be competent, be out there, be present, be confident," says Osler CCO

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Colleen Moorehead’s knack for listening and spotting trends has earned her great respect from Canada’s business community.

As chief client officer at business law firm Osler, Hoskin & Harcourt LLP, Moorehead’s job is to pick up on what’s keeping clients awake at night and then guide the Osler leadership team on how to best respond. Armed with the mantra “Companies are only successful if they think of their clients first,” she’s the influencer behind the firm’s extensive Client Listening and Reporting Program, conducting regular surveys and in-person debriefs with clients big and small to gauge their successes and discover where there’s room for improvement. She’s big on the value-add, be it making clients aware of continuing education programs, supporting their diversity initiatives or helping them respond to shifts in the global economy.

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“All of my business involvement since university has always been representing the client in some way,” says Moorehead from her perch on the 63rd floor of Toronto’s First Canadian Place. “Even as CEO of Nexient Learning or when I founded E*Trade [Canada], I always came at the business problem from a client’s perspective. That’s just the way I think about things. When I look at a brand, I try to turn it externally and think of it from the consumer’s perspective. Looking at the client first helps me frame how we could more holistically go to market.”

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Moorehead, 58, has been honing her listening skills throughout an impressive career that has delved into financial services, retail investing, institutional electronic trading and web-based services. After graduating from Wilfred Laurier University with a business degree, she climbed the ladder at Merrill Lynch and CIBC Wood Gundy and then took the helm at E*Trade, the country’s first Internet trading company. It was the mid-1990s, when Alta Vista was the search engine of choice and people were just discovering what this thing called the Internet could do beyond gathering information.

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Colleen has a big, charismatic personality, but when you are with her it is not about her but about you

“I could imagine how a consumer could have a better experience by being able to self-serve in the no-advice side of investing,” Moorehead recalls of those early days. “The Internet gave me the ability to access information. Today we all go “Duh!” but that was before there was any commerce related to using the Internet … There were a lot of discount trading companies in the banks but we were the first to really deliver it only through the Internet. … In 1996 we could do eBay − we didn’t even understand how to do that − and you could find information. But the breakthrough was being able to transact. So I did that and it was completely fun!”

Moorehead guided E*Trade Canada to become the largest independent online investment firm in Canada and then held senior business development and leadership roles with a private equity and business services firms. She met many interesting people along the way and felt fortunate to have mentors who believed in her and inspired her.

But it was Judith Elder, a Microsoft Canada executive and business visionary, who had a huge impact and channelled Moorehead’s efforts on supporting Canadian women to become corporate leaders. The two met when Elder came in to entice E*Trade to buy advertising with Microsoft and, subsequently, Elder asked Moorehead to help her with a speech she was about to give at Toronto’s Board of Trade. Elder’s message: women should be proud of their ambition, reject barriers and “make stuff happen.” It resonated with Moorehead, whose own career role models had been mostly men because there weren’t many women in leadership roles as she was moving ahead (“I can’t tell if my style has been impacted by that,” she admits). It was the early 2000s when command-and-control leadership was popular, she says − “Most Millennials would absolutely have walked out!” − and she found it refreshing to hear that ambition didn’t have to be negative when accompanied by a female voice.

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When Elder passed away soon after, Moorehead and a colleague wanted to honour her memory. They sought sponsorship from banks and telcos, got Rotman School of Management on board and launched The Judy Project, a program for women ascending into executive leadership and C-suite positions. This spring, 30 women who are one or two levels from CEO will congregate in King City, Ont., for the annual intensive week-long retreat focusing on role models, corporate culture, networking and self-reflection. To date, The Judy Project has educated more than 300 women from more than 40 national and global sponsor organizations.

“You leave with 29 other women who are equally ambitious for you,” says Moorehead, the program’s business director. “It creates ‘personal advisory boards’ who may meet for the rest of their lives.”

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While she sees progress on the diversity front, it’s still a watching brief. The mother of two sons spearheaded Osler’s General Counsel Report, a first-in-Canada client diversity reporting initiative that includes the percentage of female Osler legal professionals working on client matters as well as the percentage of Osler female lawyers at the firm overall. She’s proud of Prime Minister Justin Trudeau for calling himself a feminist and hopes her nieces will find as much satisfaction in their chosen professions while having their voices heard. She’s involved in two recent campaigns to chart new paths: #MovetheDial geared at female entrepreneurs in the tech industry and #GoSponsorHer that pairs young women with senior male and female leaders to engage in their career advancement and commit to their success.

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“Colleen has this amazing, big and charismatic personality, but when you are with her it is not about her but about you,” enthuses entrepreneur Elle AyoubZadeh, founder of luxury footwear brand Zvelle, about her mentor. “She listens and helps you make your own decisions, which is rare. She’s taught me the value of adaptability, big-picture thinking and problem-solving. You can tell her anything about any problem and she will help you find a way through it. She is a straight shooter and is non- judgmental. You’ll never put anything in front of her that will scare her. I love that even though she has achieved a lot of success in her career, she’s still hungry to do more.”

So what’s the secret to getting ahead? Be competent, be out there, be present, be confident, urges Moorehead. Put your hand in the air and take risky assignments but be sure they’re thoughtful and calculating. When women want to be mentored, it’s the role of leaders to listen and pay it forward. Someone paid it forward for her, she says. She’s simply returning the favour.

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