Every spring for the past 13 years, a small group of ambitious women have gathered at a private leadership retreat an hour north of Toronto. Over six secluded days, a new crop of passionate executives with the potential to be senior leaders has frank discussions about risk and power.
The initiative, known as the Judy Project, named after the late Microsoft Canada executive Judy Elder, is designed to help women embrace their ambition. Since its inception, more than 300 future leaders who hope to run large organizations have completed the program, simultaneously building personal networks to nurture them as they rise.
Few people have been as crucial to the project's success as Colleen Moorehead. A founding partner, she continues to serve as business development director – a fitting role for one of Bay Street's best-connected people. Now chief client officer at Osler Hoskin & Harcourt, her Rolodex – or iPhone contact list – is unimaginably big; she throws around names of powerful business people as though she just shared a bottle of red with them. Often, she has.
Young women need lines of sight to Bay Street's upper echelons, and Ms. Moorehead's success signals they can make it without having to compromise who they are. Folksy, energetic and refreshingly authentic, she is one of the few people brave enough to admit her success involved some flukes. "I feel lucky – honest to goodness," she explains over lunch at Colette, a French-themed restaurant in Toronto's Thompson Hotel. "Many of the things I did earlier in my career, I didn't realize would all knit together to this life … So I don't ever make the mistake of thinking I planned it all."
A former farm kid who grew up with five siblings in Rostock, Ont., just outside Stratford, Ms. Moorehead once sold encyclopedias to help pay for school. Despite excelling at science, and even winning a scholarship for it, she followed the advice of her older brother and studied business at Wilfrid Laurier University. (Ms. Moorehead wondered what in the world she'd do with a science degree after graduating.)
She started her career at Moss Lawson, a retail investment brokerage, because the partners who recruited at Laurier were the most interesting to talk to. They read business newspapers and translated the information into stock market ideas, and they made her want to learn more about great Canadian companies. Through the eighties and nineties, Ms. Moorehead worked her way up the ranks at Merrill Lynch and CIBC Wood Gundy, then moved into capital markets where she worked closely with Lance Uggla, who founded and runs financial information and services giant Markit in London.
"She was always a force for change, a taker of risk, and had energy to get the job done," Mr. Uggla recalled in an e-mail.
Following her first maternity leave, in 1996, Ms. Moorehead joined Versus, an electronic trading company that bought the licensing rights for E*Trade Canada. Twenty years ago, online trading wasn't a sure thing, but the bet paid off: When the company was sold to Bank of Nova Scotia in 2008, it was Canada's largest independent online brokerage.
Since leaving E*Trade (now known as iTrade), Ms. Moorehead has dabbled in different industries. First, she took a job in private equity; later she experimented with asset management. Then, in 2012, she made a splash when she accepted a position at Osler, joining Dale Ponder, a Judy Project graduate from the first retreat, who now runs the firm.
Ms. Moorehead walked into a senior role at the law firm despite not having a law degree – and that was partly by design. Gone are the days where partners served as trusted advisers to the same clients for decades. Today, law firms constantly need to pitch potential clients and win business, and must also come up with more innovative fee structures.
This pitching mentality is common in industries such as consulting and investment banking, and Ms. Ponder thought it would be helpful to have somebody from that world instill it at Osler. Colleagues of Ms. Moorehead's say she has the "oomph" they need, a warm energy that pushes partners to make new calls and forces them to rethink the way they market themselves.
Now 57, Ms. Moorehead is experienced enough to know what she's best at: executing a solid business plan – which is exactly what Osler offered. "I do very well when an organization has a vision," Ms. Moorehead says. "I can help enable; that is one of my talents." And she likes that she was hired into a five-year mandate. "I always think about work in five-year periods. It makes me feel good, having some urgency."
Chat with her for five minutes and you understand why colleagues and clients open up to her. There's a twang to the way Ms. Moorehead talks, and she exudes warmth. For our lunch of tuna niçoise, we start with butternut squash soup and by the time it arrives, I'm already talking about trying to have kids.
Despite being wealthy and living in tony Rosedale, Ms. Moorehead doesn't come across as highfalutin. While she buys designer clothes – a good chunk of her wardrobe is from Canadian designer Joeffer Caoc – she's also marinated a leg of lamb in the trunk of the car. Her justification: She was busy. "It works!"
Ms. Moorehead's large family didn't have much money when she was growing up, so she did the business co-op program at Laurier. Now that she's well-off, she's conscious of how it affects her kids. "My rosy perspective on the world comes from seeing [it] get better and better for me," she explains. "I think that's harder to instill in your kids now." To try, she sent her 19-year-old son to a school in Zambia that she supports, where he taught art last summer.
"I think we should feel fortunate that we get a shot at living these lives that are rich and have all these experiences," she says. "Yeah, you know what? There's some stress that comes with it." But now that her boys are teens, "it's a really enjoyable time for me. I can focus on what I do at work, and I can have great dinners with my kids." One is still at home; the other is in art school in downtown Toronto. ("It's good. He's cooking. He's leaving his mess somewhere else.")
Despite her busy career, Ms. Moorehead has always been heavily involved in community work. Google her name and a litany of volunteer experiences come up. Notable initiatives include her work with Covenant House, Toronto's Women's College Hospital and, of course, the Judy Project. "We're lucky enough to be in Canada; you have to give back."
It's hard to pinpoint what campaign has mattered most to her, but pushing for more diversity in Corporate Canada has certainly been on her mind the longest. She came up through the investment industry at a time when men used to openly call women "broads" on the trading floor. There weren't many senior women above her to look up to in the eighties; she relied on female peers around her own age as a support network.
To outsiders, it may seem like her efforts are designed to give other women a fair shake. She wants that, but more than anything Ms. Moorehead makes the business case for diversity. "You're a better competitor if you search 100 per cent of the pool," she says, because that means you're sourcing the best talent. She constantly stresses that it doesn't take that much more effort to broaden the slate of interview candidates – an agenda she pushes at Osler – instead of relying on the usual suspects who are often younger versions of the executive team.
Because she's so connected, women constantly ask Ms. Moorehead how to become part of such important charitable campaigns and how to get on corporate boards. "I don't like giving advice because advice is quite personal – what I know is what I know," she offers as a disclaimer. But she does have a theory: "Most good things happen to people because they put their hand in the air."
It seems rather simple, but it's a pretty succinct way of summing up her career, and also serves as a smart tip for the next generation. Jump through different jobs. Take on scary challenges. If you fail, so what?
"It's very rare that you know what the next thing is going to be," she says. "Do you worry about it? Sometimes." But she constantly tells women, who she finds are much more prone to clasping on to the sure thing, to be bold. "Something good will happen. It always does."
Where she grew up: Rostock, Ont.; attended high school in Stratford.
Education: Bachelor of business administration, Wilfrid Laurier University, 1981.
Family: Sons Liam, 19, and Aidan, who turns 17 next week.
Recent honour: 2015 Catalyst Canada Business Leader Champion for promoting women's advancement.
On adapting to how her kids communicate: "If I tell my son I'm going to send him an e-mail, he says 'What?' I have to send him a text to say I sent him an e-mail."
On cooking: One of six siblings, Ms. Moorehead was given the cook's job when her mother went back to work. That meant spending a lot of time with her grandmother and learning to love food. "If you did a survey of my friends, they would all say: 'Good place to have a meal,'" she said of her own house. Today, she loves "making bouillabaisse in the city with salad and baguette, and big cottage dinners for a crowd in the summer with family."
The sport she favours: Tennis. Has been to the U.S. Open in New York for five years running and hopes to attend Wimbledon next year.
What she watches: "I hate reality TV, it makes me want to scream. It's so forced; it's not authentic." Loves old W Network movies "when it's cold and I am tired;" HBO documentaries and old CSI episodes.