Over his time as GM with the Red Wings, Holland guided the team to more combined regular-season and post-season wins (1,098) than any other NHL franchise. The Red Wings reached the playoffs for his first 19 seasons as general manager, giving the organization 25 consecutive seasons in the NHL post-season (1990-2016) - the third-longest streak in NHL history. For his efforts, he was named the NHL's GM of the Decade (2000-09) by Sports Illustrated.
Prior to taking over as GM of the Red Wings in 1997, Holland served in a number of different roles within the organization, including as Assistant General Manager (1994-97), GM of the Red Wings' American Hockey League affiliate (1994-97), Amateur Scouting Director (1989-94) and western Canada scout (1985-89).
Internationally, Holland has served on several management staffs for Hockey Canada, helping Canada win gold medals at the 2010 and 2014 Olympic Winter Games and at the 2016 World Cup of Hockey. Holland was also GM with Canada at the 2006 World Hockey Championship in Latvia, where Canada finished fourth overall and Assistant GM at the 2005 World Hockey Championship in Austria, helping Canada win a silver medal.
As a goaltender, he was drafted by Toronto in the 12th round, 188th overall, in the 1975 NHL Entry Draft, reaching the NHL for four games with Hartford and Detroit. Holland retired as a player after the 1984-85 season, transitioning soon afterwards into scouting.
Holland played junior hockey for the WHL's Medicine Hat Tigers from 1973-75. Holland twice signed with NHL teams as a free agent - in 1980 with Hartford and 1983 with Detroit. He spent most of his pro career in the AHL with Binghamton, Springfield and Adirondack. Holland was named to the AHL Second All-Star Team in 1982 and the NAHL Second All-Star Team in 1977. He made his NHL debut in 1980-81, playing one game with Hartford followed by three games for Detroit in 1983-84.