He stood at a podium surrounded by a crush of City Council members and left-leaning advocates from protests groups like Make the Road New York and local unions.

“Si, se puede!” (“Yes, we can!”), they shouted, crammed shoulder to shoulder on a tiny stretch of sidewalk in Bushwick, Brooklyn, under the elevated subway tracks. As the trains rushed by every few minutes, the man of the hour—standing in front of a backdrop adorned with his campaign’s slogan, “One New York, Rising Together”—paused and raised his arms like an orchestra conductor, urging the overflow crowd penned behind police barricades across the street to burst into chants again.

This wasn’t a campaign rally or a protest of City Hall’s policies. It was Bill de Blasio’s first major policy rollout as mayor of New York City: a press conference to announce a deal with the City Council on legislation to expand mandatory paid sick leave.

The scene would have been unimaginable under the previous mayor, Michael Bloomberg, a data-minded technocrat who rarely embraced such theatrics. But for Mr. de Blasio–a professional political operative-turned-politician who has spent the vast majority of his career trying to get himself or others elected to higher office–the first month of governing has had many of the trappings of a campaign.

Witness the efforts surrounding his signature electoral promise: to raise taxes on the city’s richest residents to fund universal prekindergarten and after-school programs.

Last month, volunteers working for an ambiguous coalition of non-profits, unions and advocates named UPKNYC began fanning out across the city, handing out pamphlets door to door and collecting signatures at subway stations election-style as part of a push to convince reticent lawmakers in Albany to back the mayor’s tax plan.

Aiding the campaign, which kicked off with an online ad narrated by Mr. de Blasio’s wife, Chirlane McCray, is the consulting shop BerlinRosen, one of the firms that helped guide Mr. de Blasio’s electoral victory. Josh Gold, the political director of the Hotel Trades Council, who managed an independent, $1 million ad campaign that backed Mr. de Blasio in the election, has taken a leave from his job to become its manager. And Mr. de Blasio’s former campaign spokesman is handling press.

Insiders are already comparing the effort to President Barack Obama’s Organizing for America, which has tried to turn Mr. Obama’s campaign operation into a grassroots organization to promote his agenda and build support for measures like gun control and immigration.

It remains unclear who is providing the funding for this new organization, which is registered as a 501(c) (4) nonprofit group. (A representative said the group would “disclose all donors and amounts regularly” but has yet to do so.)

What’s equally unclear is whether the door-knocking will have any effect on the plan’s success, which ultimately rests upon Mr. de Blasio’s ability to sway lawmakers in Albany, including Gov. Andrew Cuomo, who has expressed deep resistance to upping taxes in an election year. (Instead, Mr. Cuomo has offered Mr. de Blasio a blank check from the state, arguably eliminating the need for the tax hikes. But Mr. de Blasio, who promised to tax the rich during his campaign, insists that only his plan will provide the reliable funding stream he needs to put the plan into practice and has rejected Mr. Cuomo’s offer.)

“If you’re the chief executive, I think you want to mobilize rank-and-file citizens, not only to support you in your next campaign, but to bring public pressure on other officials to support you now,” said Ken Sherrill, an emeritus professor at Hunter College, who nonetheless remained skeptical of the efforts. “It’s not clear to me how effective it’s been for Obama,” said Mr. Sherrill, who said only time will tell whether the efforts pay off for the new mayor.

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Campaigns are typically run in sound bites and slogans and laced with words like “hope” and “change.” Mr. de Blasio, who ran his campaign vowing to end the city’s “tale of two cities,” has continued to govern in the same style, peppering his press conferences with buzzwords like “progressive” and largely sticking to broad goals, like closing the gap between the rich the and the poor and improving relations between communities and police–aside from the pre-K campaign. Largely missing thus far, some complain, are specifics for achieving those goals, along with agendas for many city agencies, including the Parks Department and Department of Health, as well as plans for specific projects in areas like economic development or zoning.

The result has been concern among some high-level staffers, many of whom are working in agencies that remain without permanent commissioners, that they’ve received minimal direction from City Hall, leaving them confused about the new administration’s agenda and what to prioritize.

One longtime deputy commissioner described a series of meetings that Mr. de Blasio’s new First Deputy Mayor Tony Shorris had with the city department’s commissioners and deputy commissioners during his first weeks at City Hall that left some bewildered.

The deputy said Mr. Shorris “didn’t want to hear about any of the agency’s problems or the details of government.”

“Shorris just said, ‘We want to deal with inequity problems and diversity issues,’” recalled the deputy, who said that Mr. Bloomberg’s right hands had been far more invested in details. He left with the impression Mr. de Blasio’s inner circle at City Hall didn’t want to know about potential problems.

“Everyone’s just being told, ‘Be progressive.’ We’re like, WTF does that mean? What’s the fire company going to do to be progressive?” the source asked. “We know stop-and-frisk and universal pre-K [are on his agenda], but what happens after that?”

Mayor de Blasio’s press secretary, Phil Walzak, pushed back on the idea that the administration is only interested in broad strokes. “Yes, the de Blasio team is indeed focused on progressive values and tackling income inequality,” Mr. Walzak said. “But [First Deputy Mayor] Shorris, with over three decades of management experience, and other top officials have also been intimately involved in the nuts and bolts of policy and the machinery of government, working seven days a week to get the new administration up and running in a new direction.”

He pointed to the preliminary budget plan due later this month and intense work on preparing for upcoming labor negotiations with all of the city’s unions.

“From the policy details of Vision Zero [a plan to reduce traffic deaths] to the complex issues around hospitals facing closure to working with the corporation counsel on the legal elements of the Floyd [stop-and-frisk] case to developing the administration’s approach to Sandy recovery and resilience, Shorris and the entire administration have been demonstrating a proactive, engaged and hands-on approach to governing and communicating with the agencies,” he said.

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Mark Green, the city’s former public advocate and a past Democratic nominee for mayor who has sparred with Mr. de Blasio over the years, also pointed to the mayor’s willingness to weigh in on breaking news stories, like the recent controversy over Staten Island Congressman Michael Grimm, who threatened to throw a NY1 reporter off a balcony in Washington after the president’s State of the Union Speech. “Absolutely inappropriate,” admonished the mayor, when asked about the incident during a press conference. Mr. de Blasio then demanded that Mr. Grimm, a Republican, apologize to the reporter and called on House leadership to sanction him over the remarks. (In such situations, Mr. Bloomberg generally passed on the bait, choosing not to insert himself into the story.)

Mr. Green noted that 12 years as a candidate, a city councilman and public advocate eager for attention had left Mr. de Blasio adept at getting his name in the papers, even if he no longer needs to try. “It will be interesting to see if he can resist the learned impulse to grandstand and jump on the headlines, whether it’s Michael Grimm or whether it’s some stupid [New York] Post headline,” said Mr. Green, who quipped that if the mayor jumps on every questionable Post headline, he’ll have time for little else.

Others warned of political repercussions to calling out other officials–especially from the opposite party. “Being an überpartisan mayor has not been the model for a very long time,” said the deputy, arguing that Mr. de Blasio will have to be able to sit down with Republicans like House Speaker John Boehner if the city ever faces another disaster and needs federal help. “You can’t be this partisan attack dog who takes every opportunity to comment on every political thing in Washington,” he said, warning that next time Mr. de Blasio needs a favor, “They’re not going to be so nice to him.”

Mr. de Blasio is also highly attuned to the power of images and has continued crafting his folksy brand since taking office. He turned down tickets to the Super Bowl so he could watch the game on TV “just like the vast majority of New Yorkers” and then made a surprise visit to catch part of the game at his local Park Slope firehouse (a picture of which was quickly tweeted out by his office).

This Saturday, he invited the press along to film him and his famous family racing each other down the giant “Super Bowl Boulevard” toboggan run in Times Square. Additionally, his official Flickr photo feed is filled with dramatic photos clearly intended to convey specific messages, including shots of him shoveling his own sidewalk after last month’s snowstorms, in all of his everyman glory, and looking mayoral, carefully examining snow removal progress in one of the city’s emergency war rooms. At the same time, press access has been far more regulated than under his predecessor, with many more pooled and closed-press events.

Bill Cunningham, a top adviser on Mr. Bloomberg’s first campaign who went on to serve as his communications director, said that Mr. de Blasio’s approach reminded him of Mayor Ed Koch, a former congressman, who “understood the theater of the job” and used it his advantage. “Part of the job is the showmanship and the theatrics and the optics,” he said.

Mr. Sherrill also commended the mayor for embracing the demands of his public persona far more quickly than many of his predecessors, including many governors and presidents, but warned the job is far more than a photo op.

“He is very comfortable performing … But you always have to strike the balance between being a show horse and workhorse,” he cautioned. “When you have administrative responsibilities, I think it’s much harder to get a sense of how to allocate your time, of where the focus should be. And I think that’s where the jury is still out on de Blasio.”

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