Trump’s habit of self-imposing — then missing — two-week deadlines for major announcements has become a staple of his administration as it’s struggled to amass policy wins. The president has used two-week timelines to sidestep questions from reporters or brag to CEOs at the White House. But his pronouncements have also flummoxed investors, Congress and occasionally even members of his staff.

The president’s inability to meet his own deadlines highlights his struggle adjusting to the pace of Washington. It also foreshadows the trouble that lies ahead as his administration faces a series of hard deadlines in Congress over the next few months…

Trump’s penchant for casually announcing short deadlines without a plan to make good on them underscores his improvisational approach to the presidency, said Barbara Perry, a presidential historian at the University of Virginia’s Miller Center of Public Affairs. Skills the one-time reality television star honed in New York’s impulse-driven media and real-estate circles haven’t translated well in the halls of Washington, Perry said.

“For someone who bills himself as the master of the art of the deal, well, where’s the art and where’s the deal?” she said. “Trump continues to be in campaign mode with a lot of promises that he’s not fulfilling.”