Bob Hill played basketball and baseball collegiately at Bowling Green State University and was also a member of the Sigma Chi Fraternity. He attended the school during a time when college players were not eligible to join the varsity squad until their sophomore seasons; although he showed tremendous promise as a member of the freshman team, his success never really translated over to his tenure as a member of the varsity team. He then became interested in coaching.
On December 20, 1990, Hill was promoted to head coach of the Pacers after Versace's firing. He spent three seasons as the Indiana Pacers' head coach (1990–93). He led the Pacers to the NBA playoffs.
After being fired by the Pacers, Hill piloted the San Antonio Spurs to an NBA-best 62 wins in 1994–95 before losing to the Houston Rockets in the Western Conference finals. After a 3-15 start to the 1996–97 season, Hill was fired by one of his bosses, Gregg Popovich, who thereafter replaced Hill as the Spurs coach. Hill's firing at the time was puzzling to some and deeply angered Hill, considering his previous success and the fact that the poor start to the season was due in some part to injuries to David Robinson and Sean Elliott, the team's two best players.
Between 1999 and 2003, Hill was head coach at Fordham University where he compiled a 36–78 record (31.6% winning %). He was let go by the Rams following the 2002–03 season after only 1 win in the Atlantic 10. The Rams finished 2–26 in 2003, the worst record in school history. Fordham paid Hill $650,000 to leave the university in a buyout agreement four years into his 10-year deal.
He took responsibility for his rocky four-year tenure there. "Fordham was my fault; I just shouldn't have done it," Hill told the New York Daily News. "I don't want to get into why," he added. "Just blame it on me."
"I guess the best way to put it (is), I've had a really privileged career," Hill said. "I've been around a lot of great organizations; I've had a lot of great players. I've always had success to some degree, so I feel like I understand what it takes to do that and it just didn't work."
Asked to recount some of the missteps he made during his tenure at Fordham, Hill said that he made a mistake before the 2002–03 season in trying to bring in playground players such as Adrian Walton and Smush Parker. "We tried to bring the Rucker League to Fordham and it didn't work out," Hill said.
But Hill said he didn't have any regrets about his time in the Bronx. "It's a good school, good people, the whole thing, but I made a mistake," Hill said. "I don't really regret it," he added. "I've learned so much about what those young guys go through to try to be successful. It's hard for them." (Ian Begley)
On January 3, 2006 he replaced Bob Weiss as head coach of the NBA team the Seattle SuperSonics, after a lackluster 13–17 start to the 2005–06 season; he had most recently served as assistant coach for the team. He was fired over the phone as Sonics head coach on April 24, 2007.
He holds a career win-loss NBA coaching record of 312–293.
Hill has three sons with his wife Pam. The oldest, Cameron, is currently the Head Basketball Coach at Ursuline Academy in Dallas and is the owner of CHB, specializing in player development and team training. His second son, Chris, is the Head Basketball Coach at Jesuit College Preparatory School of Dallas, and his youngest son, Casey, is the head coach for the NBA D-League's Santa Cruz Warriors.