When Ted Tyndorf looks up from his desk and through his office windows on the 12th floor of the east tower of City Hall, he doesn't get a view of the skaters in Nathan Phillips Square, the shoppers and tourists bustling along Queen West or the high-rises towering beyond. Instead, Toronto's chief planner -- the guy responsible for monitoring the growth of Canada's largest city from its sprouting towers to its sprawling roads, green spaces, sidewalks and streetcar tracks -- sees a string of cubicles and desks with busy city staff scurrying among them.

That the infrastructure of bureaucracy obstructs Tyndorf's view of the city reflects the realities of the planning department he heads. Pulling together layers of complicated zoning bylaws and official plans, moderating discussions among residents and developers and dealing with an often ill-informed media is all part of his job.

Tyndorf's department is responsible for processing development applications, conducting research and gathering public input for studies and bylaws meant to determine a neighbourhood's physical growth. If a building goes up that people aren't happy about, city planners often receive much of the blame.

"[Former Eye Weekly columnist] John Sewell accused me of having approved more tall buildings in the downtown core than any other director had ever done," Tyndorf says. "I don't think it's true, but if he wants to give me credit for that, that's good because I've got all kinds of other people criticizing me for not approving tall buildings."

When I tell him I'd like to ask him about how the city manages condo proposals, concerned residents and the ins and outs of the official plan, he can't help but laugh. "I'll try my best to condense a four-year planning degree into one hour," he says.

"The city has no right to do anything except what the province has granted," Tyndorf tells me. "We really are 'creatures of the province,'" he says.

The city is required to consider every proposal that comes before it, Tyndorf explains, even if it goes above and beyond height or density restrictions in the established bylaws and official plans of the six former municipalities. Though council approved Toronto's new official plan in 2003, only a few pieces are actually in effect -- most of it is still wrapped up in more than 160 separate appeals.

"It's a real spaghetti of policy and design bylaw right now," he says.

The appeal process began in the fall, and the city will respect each section of the plan as it's approved piece by piece by the minister of municipal affairs.

"It just confuses the hell out of it even more," Tyndorf says. "Now you're dealing with portions of the plan that have been approved in combination with old plans."

Add to this mess the need to harmonize zoning bylaws and the importance of including public input, and the confusion grows. "There are 328 full-time positions spread over six different locations," Tyndorf says. "Before amalgamation, there were closer to 500 people among seven planning departments. When we hear in the press or neighbourhood meetings that we aren't doing enough, believe me, it's not that we don't want to do it; we just can't."

The Activist: Sandra Shaul

Sandra Shaul talks about other cities with about as much focus as a kid in a candy store. "My favourite city on this planet, besides Paris, is Philadelphia," she says, describing the jog she used to take every day before heading off to work -- past the Liberty Bell, the Philadelphia Museum of Art and Benjamin Franklin's grave.

Moments later, she's telling me how the restored art deco skyscrapers in Pittsburgh are to die for, how she's had a love-hate relationship with New York since she was 16 and how San Francisco's towers are so exquisite, she cried when she left.

Shaul's affection for urban architecture and design grew when her job as a web project manager took her to iconic urban centres across the United States. Back then, she spent so much time gushing over other cities, she gave little thought to her own.

Now, she could almost be considered an expert on how to calm the often tumultuous relationship among developers, city staff and residents when it comes to urban planning in Toronto. For just over a year now, Shaul has been actively involved with the Annex Residents' Association, a group notorious for stubbornly standing up to nasty developers and getting what they want. Other resident associations now turn to them for guidance, looking to the group as a model for their own negotiations.

The neighbourhood group's latest victory was regarding a proposal for 1 Bedford Road, a piece of property just off Bloor Street behind Harvey's and Swiss Chalet. The developer had originally proposed to build a condominium with two towers, 34 and 23 storeys tall. After months of negotiations among residents, city staff and developers, the proposal changed to one tower of 32 storeys and funding for a visioning study of the Bloor Annex Corridor between Avenue Road and Christie Street. The outcome was a compromise reached through hard-fought negotiations. Many residents, including Shaul, still worry the new tower will be too tall, but they're ecstatic about the promised visioning study, which they believe will ultimately guide the growth of their neighbourhood.

Shaul credits much of the group's success to its insistence on meeting face to face with planners and developers, instead of allowing city staff to keep everyone in separate rooms. "If you've worked in an office, you know that one person says they'll speak to another, and then it goes back and forth. Paranoia starts, as does miscommunication à la broken telephone ... eventually, you can't negotiate any more and each side is starting to demonize the other," says Shaul.

"We started off pretty rocky, but we ended up, I think, liking each other," Shaul says, with no shortage of praise for the city's chief planner, Ted Tyndorf, and community planner Gary Wright. "We had a face-to-face and heart-to-heart with them and they could see we weren't crazed NIMBYs," says Shaul. "We came away saying there are some things we agree on and there are some things we disagree on, but we know they're thinking."

Despite such positive experiences, Shaul remains quite critical of the overall planning process in the city.

"Yes, every application has to be considered, but it has to be considered against the official plan. If it's what I would consider a gross violation of the official plan, then why do you have to even bring in the citizen's groups?" she argues. "Why do we have to raise a big fuss? Who's doing the planning around here?"