Once there was Yankee Stadium. Now there is Coney Island.

Once there was the West Side Stadium. Now there are the West Side rail yards.

Once there was Atlantic Yards. Now there is Moynihan Station.

For just about each of Deputy Mayor Dan Doctoroff’s early development projects, there is now another similar one wending its way through a review process. The new one may be just as ambitious--and controversial--as the old, but it is infused with a vastly different sensibility, more patient in its approach, more responsive to the grass-roots community.

As he is about to step down as deputy mayor for economic development and rebuilding, Mr. Doctoroff eschews the idea that he or the Bloomberg administration went through a sea change in the way they approached development over the past six years. But it is hard to deny that he is, if not exactly more conciliatory, at least smarter about what he wants and how to get it.

“It is fair to say that we have become better listeners, and we have reached out earlier and more often to the State Legislature,” Mr. Doctoroff told The Observer in a telephone interview on Dec. 10. “On the other hand, we would not say that we did not go out and promote our ideas before. We have gotten better at it. I would not say there has been a dramatic shift.”

Still, what a shift there has been. On June 15, 2005, the Bloomberg administration announced that it supported a new Yankee Stadium. Without further ado—and in a process critics say ramrodded the project through—eight days later, it got the Legislature to set aside the park land where the ball team would build it.

By contrast, the mayor announced on Nov. 8 of this year that the city wanted to swap park land to make way for a new amusement district in Coney Island. It will hold a couple of public meetings about it, and then leisurely ask that park alienation be introduced in Albany in January, and the city expects that it will take until June to get it passed.

Here’s another example: The same rail yards where city and state taxpayers were supposed to build a platform and allow the New York Jets to build a new stadium is now the subject of a complex private-public, City Hall-Metropolitan Transportation Authority arrangement. This time around, a combination of offices, apartments and stores will be built (along with a new school, a couple of parks and a cultural facility) by a private developer, chosen through a competitive process, who will give a few hundred million dollars to the transit agency’s capital budget; build the platform on his own dime; preserve most if not all of the High Line, the old elevated train track turned park; and put aside a few hundred apartments for low-income families.

Mr. Doctoroff suggested that each of these projects has to be treated independently, and that the process—i.e., the level of community involvement—would vary.

“You cannot take a cookie-cutter approach,” he told The Observer. “Sometimes you have to seize the opportunity and still provide the community input that it deserves.”

But he also added that one of the lessons he learned is that ULURP—the name for the city rezoning process—works. The deliberative, and at times contentious, seven-month review procedure takes a project through a community board, a borough president, the City Planning Commission and, finally, the City Council—with a public hearing and vote at each step.

THIS IS QUITE a change from a few years ago, when Mr. Doctoroff and then Governor George Pataki decided to take the West Side Stadium through a state process that avoided the possible contention of city politics. But it was in Albany where Assembly Speaker Sheldon Silver killed it; a majority of City Council members ended up supporting the idea.

There is one other project like that—although it ended up getting Mr. Silver’s approval—that Mr. Doctoroff now has second thoughts about.

“I look back on Atlantic Yards,” he said. “I am a huge believer in the ULURP process. I think it makes sense. It allows the issues to be aired in an appropriate way. If it happened again, and the state were to ask if I would encourage them to take Atlantic Yards through the ULURP process, I would say yes.”

Mr. Doctoroff pointed out that, by contrast, the plan now is to take Moynihan Station, a new transit complex in western midtown, through ULURP, even though the state has bought property and plans to lease it to a private developer. When Atlantic Yards—a basketball arena and apartment village in Brooklyn—avoided ULURP, the argument was that since the train yards on which it would be built were owned by the state, it should be handled exclusively by the state.

As it happened, Mr. Doctoroff oversaw the rezoning of 78 other neighborhoods that did go through ULURP—meaning that they received the consent of the City Council. Mayor Bloomberg, in announcing his right-hand man’s departure from government (and his re-entrance into the private sector as president of the mayor’s media company, Bloomberg L.P.), said Mr. Doctoroff was more effective than any economic development official since Robert Moses while being far more sensitive to community concerns.

Alex Garvin, an architect who worked as the managing director for planning for the Olympics bid in 2005, said that Mr. Doctoroff became savvier about the way government operated.

“I think his experience with government and what existing agencies can and cannot do has changed over time,” he said. “A lot of the things which we proposed were long shots from the beginning, and nobody would have been surprised if they either happened or didn’t happen. Dan tends to pick out things that are worth fighting for.”

The stadium defeat, as humbling as it might seem to an outsider, actually set up Mr. Doctoroff’s next big project: PlaNYC, a collection of 127 initiatives to make the city more environmentally friendly, chief among them, congestion pricing. It may have been a coincidence that the city that actually won the 2012 Olympics had pioneered this system of charging cars for entering the city’s business district, but it wasn’t exactly coincidental that London had an equal, or greater, reputation for livability as New York.

“When I was traveling around the world understanding how they were evaluating the different cities that were bidding, I also gained a much deeper understanding about what New York’s competitive strengths are,” Mr. Doctoroff said. “It reinforced this view that New York is in a fierce competitive battle for employers, residents and visitors, and we have to continue to strive to think about the city’s future and prepare for it with the way we use land, the way in which we use infrastructure, the way in which we serve residents and businesses, the way in which we treat our environment. I am constantly aware of the way in which other cities emulate New York, and if we don’t stay out ahead, there will not be a very happy result.”

Mr. Doctoroff, in fact, ended up commissioning a $523,000 report shortly after the failed Olympics bid on how the city could stand its ground against London; according to the report, 32 percent of senior executives surveyed found that London was a better place to live than New York, while 30 percent thought the opposite.

Congestion pricing was supposed to help by raising money to build out the transit system and discourage commuters from using cars. It, and the whole PlaNYC, came about through a deliberate, open process in which Mr. Doctoroff’s staff held dozens of meetings with officials, community groups and regular citizens. The mayor set up a panel of labor leaders, real estate representatives, planners, environmentalists and City Council members to mull the issues over. And yet, despite all that foundation work, once the mayor announced his support for congestion pricing in April, it ran into the same problem that the stadium did: resistance from Mr. Silver and colleagues in the State Assembly. Could it be that Mr. Doctoroff made the same mistake twice?

Mr. Silver, Governor Spitzer and Mayor Bloomberg eventually worked out a compromise, sending the congestion pricing issue to a commission made up of representatives from all levels of government that will recommend a congestion mitigation plan by the end of January. It is, for matters that are not about land use, the next best thing to ULURP. Mr. Doctoroff, this time, will be watching from the sidelines to see if it works.