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City Hall’s council and support services director Winnie Li says her career these days isn’t that far off from her days as a journalist, holding governments to account.Kevin Van Paassen/The Globe and Mail

After Toronto City Council's decision to strip Mayor Rob Ford of most of his powers in November, 2013, most city hall-watchers were preoccupied with the political fallout from the stunning move – but Winnie Li was focused on more practical considerations.

Ms. Li, the long-time head of council and support services at Toronto City Hall, immediately began making plans with her team: How many workers would need to work overtime to move Deputy Mayor Norm Kelly, who took over most of the mayor's powers, into his new office? What kind of furniture would he need? What kind of paperwork would be needed to transfer the mayor's staff to the deputy mayor?

As one of hundreds of employees at City Hall, the soft-spoken Ms. Li is just one of the many behind-the-scenes workers at the city who kept things running smoothly throughout the turmoil of the Ford mayoralty. And, as Mr. Ford's term comes to a close and mayor-elect John Tory is sworn in next week, she is a key figure in ensuring a smooth transition.

"Basically, the bottom line is to make sure that their offices function optimally," Ms. Li said. "I see all 44 councillors as running their own offices … So the role of myself and my team is to provide the support for them to run their offices the way they need it to run."

Ms. Li oversees a team of 56 people who co-ordinate most of the back-end services for the councillors: human resources support, accounts payable and expenses, and IT services. If a councillor needs new furniture, or to expense a cellphone bill, or to fix a photocopier, Ms. Li is the one they call.

Right now, her biggest job is figuring out the logistics of moving the non-returning councillors out, and the seven new councillors – as well as Mr. Tory – into their new spaces.

"I call Winnie when I have issues overarching … staff, budgets, and everything else that goes on, and a lot of rules that we have to follow," Councillor Paula Fletcher said. "She's very helpful."

Ms. Li, 60, has had a long and varied career in public service. After growing up in Hong Kong, she completed her sociology degree at the University of Chicago, before earning a journalism degree at the University of Missouri.

"I was in the United States during the Nixon and Watergate era – so that's the whole background – the media, the fourth estate, providing the voice to the people and holding governments accountable."

She worked for a year at The New York Times' Hong Kong offices as a researcher and translator – and wrote about a dozen stories on a diverse range of issues, including the Vietnamese boat people – but the time difference between New York and Hong Kong meant that most of her shifts were overnight, which became unmanageable.

After many years of working in communications and public relations, she moved to Canada at the age of 35, when she was the the communications person for several city departments, before taking the lead in 2003 on the city's efforts with the SARS economic recovery campaign.

In the nine years she's been in her current role – and partly because of the diverse services her department provides – Ms. Li has become a go-to for councillors for any range of matters.

"Winnie's great. Winnie just kind of helps us run our lives," Councillor Josh Colle said.

A few years ago, for example, when a raccoon was discovered on the second floor of City Hall, it was Ms. Li whom several councillors called to take care of the problem. She put them on to building management.

And Ms. Li, whose daughter recently gifted her with copies of her old articles from The New York Times archives, said that her career these days isn't that far off from her days as a journalist, holding governments to account.

"In making government work, there's the decision-making process, but there's also the need to make the elected officials function," she said. "The ability to make elected officials' offices function in an optimal manner – I see it as really a fundamental foundation for a local democracy."

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