Monson began at GU as an assistant coach in 1988 before being elevated to associate head coach under head coach Dan Fitzgerald in 1994; in all, Monson spent eleven years helping build the Gonzaga program. As an assistant, Monson was a key figure in the Bulldogs turnaround during the 1990s. Gonzaga had a record of over ten seasons and he was responsible for recruiting many of the key players in Gonzaga's NCAA Sweet 16 appearances from 1998–2001. From the time Monson was named associate head coach in 1995, Gonzaga averaged 22 wins per season and reached postseason play every year but one. For all of this, Monson was elevated to head coach of the Zags in 1997.