After retiring, Grimson finished his undergraduate degree and began work on a law degree. He completed his law degree in December 2005 at the University of Memphis Law School. He was In-House Counsel for the National Hockey League Players' Association (2006–2008) and then worked for the Nashville law firm of Kay, Griffin, Enkema & Brothers, PLLC (2008–2012). He worked as a Color Analyst for the Nashville Predators on Fox Sports South and the team's flagship network, 102.5 The Game, through the 2016-17 season