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Mr. Gray and the city administrator shouldn’t take a piecemeal approach, said Stan Jackson, who served three D.C. mayors and as interim president of the University of the District of Columbia.

“The earliest and biggest challenge is devising a forensic analysis of the finances,” said Mr. Jackson. “What are the true resource allocations and how are those allocations spent. … On the jobs front, are we integrating bricks and mortar with human capital? … On economic development, do we understand the importance of being civically engaged?”

Mr. Gray campaigned on a theme of “One City,” and he urged civic leaders at a breakfast on Saturday to help him the bridge the real and perceptive divides in voters’ minds.

“Open communications and trust between the city officials and civic leaders. That’s what Vincent Gray said,” noted Robert Brannum, president of the D.C. Federation of Civic Associations.

A longtime critic of former Schools Chancellor Michelle A. Rhee, Mr. Brannum also said the Gray administration must “start protecting jobs for people who live in the District” and that there is no shortage of stakeholders who would willingly be a part of his “kitchen Cabinet brain trust.”

Mr. Jackson cautions that Mr. Gray should act with deliberate speed to align fiscal policy with the programs that mayor-elect laid out during the campaign.

He also said city leaders must be mindful that the control board, which Congress created too oversee District government because of financial mismanagement, is merely dormant - not dead.

“There is no margin for error,” Mr. Jackson said.