Prior to entering politics, Dockrill was a member of the Nova Scotia Government Employee's Union and a receptionist at a Cape Breton health care facility.
Changes to laws governing unemployment insurance, restrictions on the fisheries, the slow destruction of the area's coal mining industry and problems with health care services all contributed to a growing sense that Dingwall was out of touch.
[citation needed] Dockrill ran an aggressive campaign, assisted by resources directed to the riding by then Nova Scotia NDP Provincial Secretary Ron Cavalucci.
She worked tirelessly on the issue of the coal industry, the last Cape Breton mine was closed soon after her defeat in the election of November 2000, when she lost in a landslide by Liberal Rodger Cuzner.
In 2004 Dockrill, who had returned to her previous position working in a health facility, ran for and lost the NDP nomination to newcomer Shirley Hartery, who went on to be defeated by Cuzner in the June election.