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“Over the last 10 years, I’ve worked with over 1,000 community organizations,” she said. “I know the people that will deliver, the people who will open up to have those conversations and the ones who will stay on the sidelines. And that all helps in this.”

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When the campaign began in earnest last February, Ms. Latif wasn’t on Mr. Tory’s team. She spent the first several months volunteering for a rival, councillor Karen Stintz. She made the switch only after a concerted lobbying effort that began in March over coffee with Bob Richardson, Mr. Tory’s campaign co-chairman.

She said one big reason she moved was Mr. Tory himself, and the relationships he had already built in the communities she targets. Back when they both worked at Queen’s Park — her for Mr. McGuinty, him as the leader of the opposition — Ms. Latif would regularly try to book the premier for community events, only to find Mr. Tory already on the roster.

She found the same thing happening when she started on the Stintz campaign. “[Ms. Stintz] has spent a lot of time in politics, but not actually building those relationships,” she said. “Whereas someone like John, in the years he’s been a radio host, he’s still showed up to those events. He’s been to the Tamil Chamber dinners. He’s talked about important issues … and those relationships were still solid.”

Ms. Latif said there’s no science to her job. “A lot of it’s about gut and past relationships.” While many communities want to hear about one or two issues in particular, she said for most the overall message doesn’t really need to change.