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An Incredible Story of Continuous Growth: Jessica LeCroy

Women of Influence sits down for an exclusive interview with Jessica LeCroy, lawyer, diplomat, independent corporate director and Mississippi farmer.


She was a senior strategic advisor to generals in Iraq, and assisted in the opening of the first U.S. Embassy in Tbilisi, Georgia, after the dissolution of the Soviet Union, even learning the Georgian language in the process. From 2004-2006, LeCroy was Canada’s U.S. Consul General in Toronto, and for three years after retiring from the American Foreign Service, she’s most recently been a senior advisor in the Toronto office of business law firm Bennett Jones LLP.

Asked to explain her unusual career trajectory, she shrugs. “I guess I may be a little ADD!” And when asked where she calls home, she responds, “Wherever I am standing at the moment.” Regarding her attachment to Toronto and Canada, she observes that not enough accurate comparative critical analysis of policy differences between the U.S. and Canada is done to inform the electorates of each country. Indeed, she wrote an article on this subject when she was a visiting senior fellow in geo-economics at the Council on Foreign Relations in New York, entitled “Can Canada Be as Innovative, Competitive and Entrepreneurial as the U.S.?”

Except for her Southern accent, one would never guess that LeCroy grew up in the rural northern Mississippi where most people stayed put in their communities for life, women “glowed” as beauty queens and racial segregation was entrenched. Her widowed mother, who had assumed sole responsibility for managing the family farm and agribusinesses, sent LeCroy and her younger sister to a girls’ boarding school in nearby Memphis called the Lausanne School (now the Lausanne Collegiate School). Lausanne was one of the first schools of its kind to accept blacks, Jews and other minorities as students. It broadened her worldview. “They reinforced my own family’s simple message: properly educated, and with a modicum of initiative, just about any dream can be realized by anyone, no matter what the obstacles may be,” she says.

“You see,” LeCroy explains, “my mother was under the illusion that the strong, independent professional women characters she saw in the movies portrayed by Rosalind Russell, Katherine Hepburn and Barbara Stanwych were real, that they actually existed in critical mass, and that was what she wanted for her four daughters, come hell or high water.” In 2010, the Lausanne Collegiate School honoured LeCroy with its prestigious Chair of Ideas award, carrying on its tradition of a distinguished lecture series that included Margaret Mead, Aldous Huxley, as well as, more recently, other Lausanne graduates like the actress Gennifer Goodwin.

From that progressive girls’ school in Memphis, she became one of the early women undergraduates at the previously all male University of Virginia. Then followed graduate school and finally law school at Boston University. She claims she was too busy with friends, work and school to take too much notice or let herself be too affected by discrimination against women, though it clearly existed. When LeCroy’s mother died when she was in college, she managed the family businesses – a cotton gin, feed store, fertilizer distributorship and farm – for a while. She invested most of her inheritance in education at numerous institutions and programs. After passing the Texas bar, she worked briefly as a corporate and banking lawyer in Dallas, the firm’s first woman associate.

It seems LeCroy’s life has always been one of constant transition, adaptation and growth. On impulse, at the suggestion of a law school classmate, LeCroy took the U.S. Foreign Service exam and passed on the first try. That kick started a 25-year diplomatic stint and promotion into the exclusive rank as a career member of the U.S. Senior Foreign Service. “I knew very little about the Foreign Service,” she says, “but I thought I would always wonder what I had missed if I didn’t seize the opportunity.” She never intended to make diplomacy a career, she adds, and would come close to resigning several times.

LeCroy held a dizzying array of positions overseas and in Washington and New York. Nicaragua, her first assignment, was “the year of living dangerously” during the Contra War where she started out as a human rights officer and was pegged as someone who could ‘do’ conflict zones. In contrast, The Netherlands provided “a great social life.” Bosnia was “an eye-opener that war and atrocities could occur even in Europe.” In Tbilisi, Georgia, she also shepherded a vision of a trans-Caucasian oil pipeline transit through the country, meeting with President Shevardnadze and other Georgian officials. Up next came Iraq, where she was personally requested as one of the first, if not the first, Foreign Service officers to serve out a year’s assignment. She was asked to return three more times on a development research team focused on supporting entrepreneurship. Her role? “Let’s just say ‘unwilling accomplice.’”

It wasn’t just overseas where she found her excitement. “Many of my domestic assignments were just as interesting and challenging,” says LeCroy. She refers to her time at the Treasury Department, as a congressional fellow on the Hill working trade and foreign policy issues for Congressman Berman of California and Senator Bill Bradley of New Jersey, as a civilian graduate of the National War College, and time spent at the Council of Foreign Relations. As a relatively junior officer, she served as a deputy director in the Office of Counter-Terrorism and would, in another assignment, go on to lead a large telecommunications delegation on repeated visits to Paris to negotiate with other Western governments for the transfer of sensitive technology to the then Soviet Union. She quotes with animation a veteran ambassador admonishing her as a junior officer that she seemed to be “suffering from the illusion that hard work alone is going to get you ahead.” His advice? “You’ve got to learn to suck up!” A lesson, LeCroy adds, she never learned.

It is important to know, she points out, there have been moments of despair and disappointment when she believed her high-risk professional life was finished. At those times she had rock-solid moral support from her sisters and close friends. But the key to always landing on her feet, she says, were “rescue champions” who would appear, often out of the blue, to guide her up the professional ladder and around seemingly impossible obstacles and resistance. She doesn’t think they would want to be acknowledged by name. “They know who they are,” LeCroy says, noting that most of these rescue champions were in fact male, many with names that would be instantly recognizable. LeCroy also admits to having prepared “a rescue package” for times of failure. This consists of a copy of Yeats’ poem, “To a Friend Whose Work has Come to Nothing,” the recording of the CBC business reporter review mentioned at the beginning of this article, and some special emails of support over the years from a professor at the War College, former bosses at the Treasury and Defense Departments, and a few others, including colleagues at Bennett Jones.

Her greatest professional skill at this point in her career, LeCroy says, is as a business strategist. In the business world, she notes, change is ubiquitous. She relishes being thrown into topics she knows little about. That gives her a clean slate, with few prejudices or preconceived notions. From that perspective, she is able to identify new dots no one else sees, rather than merely connecting dots that already exist. A pattern has evolved over time where she has been duly called on to sit with a table of experts on a selective subject matter or sector to review game plans or tackle a particular problem. “I listen, I ask questions, and then I say, ‘have you thought about this as a possibility?’ And it is simply thrilling to see eyes spark and synapses fire.” As is often the case, the experts themselves readily admit to being too bogged down by details and boxed in by the parameters of the problem to contemplate creative solutions.

She cites a long list of examples where this kind of design thinking had been applied during her careers in business, law and diplomacy. Most recently in the non-profit world, she suggested that the International Women’s  Forum (IWF)’s water initiative work with the Prince Charles ‘seeing is Believing’ project for urban aboriginal youth, where she had been recently invited to join the advisory board. Working with local colleges and technical schools, she proposed there might be training opportunities to address critical clean water issues on reserves where these displaced youths could be purposefully employed. This would be a collaboration that would meet everyone’s objectives. As U.S. Consul General in Toronto, she had established an aboriginal officer portfolio for the consular section; it was an issue close to her heart.

LeCroy maintains that one can gauge the value of any country by the way it treats its minorities and disadvantaged. In this regard, she points out, Canada’s promotion of inclusiveness is recognized as a model globally. The Progressive Muslims of Canada is another organization she actively supports, and attending their Eid and Canada Day celebrations each year are priority events on her calendar.

While Toronto has been her base for the past several years, LeCroy’s focus has turned back home where she is needed to help wind down the remaining family businesses. She is also renovating long-distance the apartment she has owned in Dallas for the past 30 years. She remains on the board of directors and advisory boards of several Canadian entities: a high-tech start-up based in Montreal, the veterans’ palliative care centre McDermott House Canada (MDC) which just launched a Friends of MHC organization in the U.S. to which she belongs, the International Women’s Forum Toronto chapter and the Canada-U.S. Law Institute. She is also a member of several mining industry professional organizations. As President of the Toronto chapter of the Organization of Women in International Trade (OWIT), LeCroy was recently in Toronto to attend their annual awards gala being held at the Toronto Board of Trade, where we caught up with her for this exclusive interview.

Looking to her own next stage of professional growth, LeCroy sees herself as most useful in the role of independent director at a public company that is global or intending to go global. “Corporations are actively looking for women to serve on their boards,” she says. “They are also looking for people with international experience.” And with LeCroy’s seemingly borderless career, she’s got that in spades.

With all of these incredible stories, is a memoir in her future? “No, never!” she exclaims, adding, “I am a behind the scenes kind of person – discretion is the better part of valour. If I had my way, there would be awards for people who refused to write memoirs.” As U.S. Consul General, LeCroy gave only one interview, to The Globe and Mail, though she had many public appearances to explain U.S. positions, policy and initiatives to the Canadian public. Now she accepts mostly off-the record requests. She recalls a reported comment from former Mississippi governor and Washington insider Haley Barbour when he visited Toronto, just after she had left her post as Consul General, asking why, as a fellow Mississippian, he had never heard of her. “I intend to remain a private person,” she says.