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Ian Robertson poses for a photograph in the business district of downtown Toronto, on Oct. 18. While working at Kingsdale, Robertson realized that his political skills were transferable to the world of proxy contests and hostile mergers and acquisitions, which inspired his new company: a leadership advisory firm called the Jefferson Hawthorne Group.Christopher Katsarov/The Globe and Mail

As the chief executive officer of Kingsdale Advisors, Ian Robertson spent his days rescuing companies in crisis.

During his 10 years at the company – first as executive vice-president of strategic communications before transitioning to the top job – Mr. Robertson says he navigated clients through 147 proxy fights. What he learned was that, in most cases, there had been clear warning signs, which were either ignored or missed.

It was this realization that inspired Mr. Robertson’s new company: a leadership advisory firm called the Jefferson Hawthorne Group, which launches this week.

“Kingsdale is the best emergency room in Canada. I saw a need for preventative medicine,” he said.

Before becoming one of the most notable figures on Bay Street, Mr. Robertson spent nearly 20 years in politics, culminating in his roles as campaign manager and chief of staff to former Progressive Conservative leader Tim Hudak. At the Jefferson Hawthorne Group, Mr. Robertson says they’ll be helping boards and CEOs think through high-stakes issues – reputational risks, succession planning, geopolitical issues – the way political campaigns do.

Mr. Robertson’s exit from Kingsdale is among a number of other recent high-profile departures, most notably Kelly Gorman, who last month became the chief executive of Advocis.

Anna Fernandes, the vice-president of strategic shareholder advisory and analytics, also left in September. She told The Globe and Mail over LinkedIn that the “departure of several esteemed colleagues” caused her to “explore new opportunities that align more closely with my vision for the future.” She added she was grateful for the opportunities Kingsdale provided.

Andrew Sidnell, who spent two years as vice-president special situations, has also parted ways with Kingsdale. He is one of Mr. Robertson’s new partners at the Jefferson Hawthorne Group; Daniel Gordon, whose career has also toggled between senior roles at Queen’s Park and Bay Street, is the third partner.

Mr. Robertson told The Globe that the recent turnover at Kingsdale is a timing coincidence, and that when he took over as CEO three and a half years ago, he told founder and executive chair Wes Hall that his plan was to stay for three to five years.

“Wes has been an excellent mentor,” Mr. Robertson said. “Kingsdale is the best bootcamp you can find for learning how to deal with the rough and tough world of corporate Canada.”

In an e-mail, Mr. Hall said he is “proud of my people when they move on to greater opportunities,” pointing to the example of Ms. Gorman, and added that Kingsdale has “an extremely deep bench” of talent. Senior vacated positions will be filled with internal candidates.

“If Ian puts the same kind of effort he does in his business as he did while here at Kingsdale he will do just fine,” Mr. Hall wrote.

Mr. Robertson, 46, was born in Belleville, Ont., as the son of two teachers. The family moved around rural Ontario, eventually landing in Brampton by junior high.

He caught the politics bug as a teenager and spent the 1995 provincial campaign hammering in lawn signs for Progressive Conservative leader and eventual premier Mike Harris. It was an interesting choice for a kid whose parents worked in education, given Mr. Harris’s frequent criticism of school boards.

“There were deep sighs,” from his parents, Mr. Robertson recalled. “And I remember putting the law sign on my front lawn and it being gone by the end of the day.”

From there, it was onto Western University where Mr. Robertson was a devoted member of the young conservatives. He wrote his last exam and drove to Toronto to start work at Queen’s Park on the same day. His first job was as a “general assistant” – coffee and bagel fetcher – but he quickly showed a knack for speech writing.

By the age of 24, Mr. Robertson was the director of communications for Ontario’s minister of health, Tony Clement, overseeing issues such as West Nile, the SARS crisis and 2003 blackout.

When voters kicked the PCs out of office, Mr. Robertson switched to the not-for-profit sector, working with the Mount Sinai Hospital Foundation and then ChildFund International. In 2009, it was back to Queen’s Park for five years under the new PC leader, Mr. Hudak.

When that chapter came to a close, Mr. Robertson met Mr. Hall at Kingsdale and realized that his political skills – convincing people to vote a certain way, manoeuvring through difficult scenarios – was transferable to the world of proxy contests and hostile mergers and acquisitions.

Jefferson Hawthorne Group is a continuation of this work. For example, they’ll be using political techniques to guide decision-making.

“In politics you’re always doing these exercises called war games. Every decision you’re thinking: What are the other guys going to do? What will these stakeholders do? On Bay Street, because of the demands, people tend not to think through the whole suite of risks,” Mr. Robertson said.

One recent example was the rush that some companies felt to make a statement after the Oct. 7 attack by Hamas, he said. Tweets were made without thinking through how the words would be received by staff, executives, customers and shareholders – none of whom are a monolith.

“Leaders now are confronted by a broader set of stakeholder interest than ever before. And it causes them to make a bunch of decisions that they didn’t have to think about when doing their MBAs.”

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