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the lunch

Illustration of corporate director Sheelagh Whittaker.ANTHONY JENKINS/The Globe and Mail

Shortly after our lunch of sautéed vegetables and grilled Orata fish is served, Sheelagh Whittaker begins dishing out confidences.

Maybe it's the setting. We're seated at a corner table at the back of La Fenice, a crowded restaurant in Toronto's theatre district. It is the very table, my dining companion allows with a spreading smile, that she and two other business chiefs frequented in the mid-1990s to escape the stuffy confines of the business establishment "to let our guard down."

At the time, Ms. Whittaker was chief executive officer of the Canadian branch of U.S. data processing giant Electronic Data Systems (EDS). Her lunch mates were Maureen Kempston Darkes, then president of General Motors of Canada Ltd., and Diane McGarry, then chief executive officer of Xerox Canada Inc. Over a five-year period, the trio gathered every three months or so to laugh at the missteps or cheer the triumphs that came with being pioneering female CEOs.

"It was a chance to be with peers who were like you, which wasn't that common," Ms. Whittaker recalls. "When we were together, we were frivolous and frank. … It was totally safe, you knew no one would ever hear about it."

The unguarded getaways were necessary therapy because, according to my dining guest, there was little room for spontaneity in the tightly controlled ranks of the business elite. Board meetings were run with "militaristic" precision, directors were closely connected by schools and clubs, and uninvited boardroom inquiries were often "squelched."

The problem, Ms. Whittaker says, as she stabs a flaky, sweet morsel of fish, was that boards were often run by "command and control" CEOs who answered to directors only too willing to be controlled.

Nothing took forever to happen.

"I have, in my life, read books in the washroom because the meetings were so boring," she says, with great, gulping laughter.

Ms. Whittaker has been startling Canada's clubby business community with her tart assessments since she first rose to prominence in 1988 as the CEO of the startup Canadian Satellite Communications Inc. Back then, she was a tireless advocate for the promotion of female executives.

Today, at the age of 63, she is as provocative as ever, even though her career has taken her deep inside the business establishment. Based in London, she serves as a director with British insurance giant Standard Life PLC and Calgary's Imperial Oil Ltd., where she views herself as part of a more enlightened generation of directors seeking to "stamp out personal and corporate complacency" in the boardroom.

"I guess I have always had this frankness. It was never calculated, but it stood me in good stead," she says.

She was probably Canada's first CEO to introduce herself as a feminist and, more recently, hardened her stand on advocating quotas to boost stubbornly low levels of female directors.

As a director of a variety of major corporate boards, including former posts at Royal Bank of Canada and CanWest Global Communications Corp., she is not shy about chastising sleepy directors who turn a blind eye to business failures. She is full of praise for controversial shareholder activists such as Bill Ackman, who rocked the board of Canadian Pacific Railway Ltd. in a successful proxy contest in May. After years of shareholder indifference, activists are creating a "much healthier" corporate environment by prodding directors to be more vigilant, she says.

She regard's Mr. Ackman's successful ouster of CP's CEO, chairman and five directors as "a cautionary tale for other directors to learn from."

The lesson is that even the most prominent boards can no longer ignore shareholders when their companies have missed financial and operating targets for years. By fighting Mr. Ackman, she says that Canadian Pacific's board "was effectively saying … for whatever set of reasons, that they were tolerating underperformance."

That Ms. Whittaker has the confidence to be so critical reflects in part the disintegration of a what she calls the old "lobster" and "limousine" days when she was first appointed a director at Canadian companies in the 1980s.

It would have been unthinkable until recently for a director to question the actions of another board. She says it is possible today because there is lot more "hand-wringing" about potential risks in the wake of the financial crisis and increased shareholder and regulatory scrutiny.

She calls this boardroom shift "a journey from self-satisfied smugness to self-doubt. … You should be worried if directors are not questioning the status quo."

Ms. Whittaker's independent streak was forged at an early age, in a family preoccupied by her mother's crippling multiple sclerosis. The disease rendered her mother an invalid when Ms. Whittaker, her two sisters and a brother were young. Her father had limited time for parenting. The children were forced to shoulder a greater share of the domestic responsibilities and had to learn to be pragmatic about life's harsh realities.

"We were largely motherless children," she says. "We had to face reality and just get on with it. … There was not much room, or even patience, for any guile."

At EDS, she flourished in a company that embraced strong opinions. The company was founded by Ross Perot, the legendary plain speaker and failed U.S. presidential contender, who once dismissed fellow General Motors' directors as "pet rocks" after they blindly supported the auto maker's then-CEO Roger Smith.

Ms. Whittaker joined EDS in 1993 after Mr. Perot sold the company to GM (it was later sold to Hewlett-Packard Co.), but she says "his direct style and his fingerprints were still all over the company."

After an eight-year stint in Canada, she was repeatedly promoted at EDS to run divisions in Great Britain, Australia, Africa and the Middle East; she retired in 2005.

With more time on her hands as a director, she has found a new outlet for her sharp observations: writing.

Her first book, The Slaidburn Angel, was published by Dundurn this fall. It is an unflinching examination of a sensational infant murder case in the 1880s against two sisters on her father's side of the family. Woven into the story are what Ms. Whittaker calls "meditations on loss" in her own family. Her mother died when Ms. Whittaker was 18, and, years later, one of her sisters began a long struggle with mental illness.

Few business leaders are so forthcoming about such difficult family issues. Ms. Whittaker, however, says she "never gave a thought to filtering the truth."