A native of Newton, Massachusetts, Cadiff originally enrolled in pre-med at Harvard University, but low marks in science forced him to reconsider. He chose a special concentration in the history and literature of theater arts and was the assistant director of Harvard's Spring 1974 production of Kiss Me Kate. After that, he immersed himself in directing with more college productions. While an undergraduate, he met Hal Prince, the famed Broadway producer.
After Cadiff graduated magna cum laude in 1977, Prince offered him a position as assistant stage manager for the Broadway show On the Twentieth Century, and he moved to New York City to begin his career. Eventually, he began writing and directing his own plays, including the award-winning musical play Brownstone, as well as the Drama Desk Award-winning off-Broadway play 3 Guys Naked from the Waist Down and MAIL, which was presented at the Kennedy Center as well as on Broadway.
He made the move to television directing with several episodes of the popular sitcom Growing Pains, followed by the sitcom Empty Nest. As a director and producer of the hit comedy series Home Improvement starring Tim Allen, Cadiff won a People's Choice Award and the Humanitas Award. On Michael J. Fox's comedy, Spin City, he served as executive producer as well as director and and was honored with a Genesis Award and an International Monitor Award. Cadiff made the move to feature film directing with an adaptation of the legendary television series, Leave it to Beaver (1997), for Universal Studios.
Additional television directing credits include ABC's According to Jim and My Wife and Kids. For the fall of 2003, Cadiff directed the pilot of the ABC comedy It's All Relative. His second feature as a director was Chasing Liberty (2004), starring Mandy Moore and filmed in England.
Leave it to Beaver (1997)