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Planner Rollin Stanley July 6, 2012 in Calgary.Laura Leyshon

When Rollin Stanley worked for the City of Toronto, he often joked that he didn't "do suburbs."

Last month, shortly after he started a new job as Calgary's top planning official, a local alderman presented him with a bumper sticker that read, "I do suburbs, and I do them better."

After stints in two U.S. cities, Mr. Stanley has returned to Canada with a mandate to help Calgary build subdivisions that are more compact, higher density, and accessible to transit.

"They know where they want to get to," he said. "My job is to help them understand how they get there, and helping them define what that vision is."

He steps into the job at an interesting time for those tasked with urban design, when economic uncertainty is kneecapping municipal budgets and the pressures of suburban sprawl, downtown development and aging infrastructure are becoming impossible to ignore. And Mr. Stanley is not alone in his challenges: Several major Canadian cities are looking to replace their chief planners, a hiring spree that could significantly change the country's urban landscape.

Toronto's chief planner has retired, while his Halifax counterpart has moved to an academic posting. And Vancouver is looking to replace its director of planning, Brent Toderian, who Mayor Gregor Robertson fired in January, saying he wanted the city to re-focus on housing affordability.

All the turnover is worrisome, says Joe Berridge, a Toronto planning consultant in the private sector, because of the complex, vital role these bureaucrats play in a city's development.

"There are very few people around in the world who can do it well. It's like being a concert master," he said. "That's why there's such a dearth of candidates for your Vancouvers and Halifaxes and Torontos."

The churn also raises a nagging question about the role of these influential municipal officials: do fast-growing cities need – or indeed, want – visionary chief planners? Or do they actually require can-do administrators who have the contacts and political savvy to deliver change in modern metropolitan areas?

The biggest threat, according to Larry Beasley, Vancouver's former co-planning director, is that the position will be devalued, or submerged in bureaucracy.

Chief planners must be risk takers, he said, and play the role of the "enfant terrible" in municipal governments.

There's little doubt that forward-looking planners have made dramatic differences in places like Copenhagen, New York and Melbourne, bringing life surging back into central areas that had either been choked with cars or semi-abandoned.

And although Canadian cities are largely thriving, that does not mean the next generation will have it easy.

The new challenges revolve around livability and sustainability, especially in car-dependent suburbs that aren't well served by transit. Many of today's top planners, including Mr. Stanley and Mr. Toderian, promote similar ideas – green buildings, cycling, pedestrian-friendly streets, accessible waterfronts and transit-oriented development.

Yet much of what they're able to implement will depend on political and regulatory context. In U.S. cities with strong mayors, leaders like New York's Michael Bloomberg can hand-pick top planners to execute their agendas. In Ontario cities, planners' recommendations are routinely vetoed by the Ontario Municipal Board.

Each Canadian city looking to replace its top planner has unique advantages and obstacles.

In Vancouver, Mr. Beasley said he succeeded because the job of planning director was split in two, allowing him to concentrate on large- and small-scale vision while Ann McAfee oversaw the department's administrative responsibilities. But even with that setup, chief planners must sell their ideas to voters, and Mr. Toderian reportedly ran into opposition from ratepayer groups. He's now in private practice.

In Calgary, Mr. Stanley has the benefit of an ambitious master plan and a progressive mayor, Naheed Nenshi. But the city has sprawl issues, and Mr. Nenshi said the priority is to find "sensitive" ways to add density and vitality to the city's older suburbs. "That's why Rollins' job is unbelievably critical," he said.

The 54-year-old barely had time to unpack his suitcase before he began conferring with developers about zoning changes that could foster better suburbs.

"We've already had an impact in the three weeks I've been out here," he said.

In Toronto, a search is under way for a new chief planner, who will have to hustle to keep abreast of an unprecedented high-rise building boom even as the city struggles to find cash to build transit lines, improve public space and accelerate waterfront development before the 2015 PanAm Games.

"The right person could triumph over what are undoubtedly tricky bureaucratic, administrative structures in city hall," Mr. Berridge said.

Toronto chief planner Paul Bedford negotiated similarly stressful times in the mid-1990s, and manged to push through a plan allowing the conversion of old downtown warehouses into offices or condos – a radical move that brought waves of new investment and residents to the core.

He credits advice from his mentor, Jane Jacobs, who told him to be bold and outspoken. "`If you're going to do something,'" she counselled, "don't do it in a half-assed way.'"

Mr. Beasley remains optimistic that Canada's urban visions will be crafted by the right hands. He believes many top planners from U.S. cities will be eager to work north of the border, where budgetary dilemmas look manageable by comparison.

And he says up-and-coming Canadian planners now moving into senior positions have impeccable credentials and a global outlook.

"The new generation, it's their time to take over," he said. "I think you're going to see some wonderful new initiatives across the country over the next few years."