For the first year after the end of his playing career, Worsfold worked as a commentator with Channel 7. At the end of 1999, Worsfold confirmed that he was interested in coaching and that he was willing to move away from Perth in order to do so. He was subsequently offered a full-time assistant coaching position at both West Coast and , and was at one stage considered a possible candidate to coach following Gary Ayres' decision to leave the club to coach . Worsfold also interviewed for the vacant senior coaching position at , along with Chris Connolly, Mark Harvey, and Peter Schwab, but was turned down in favour of Schwab. Worsfold finally signed a three-year contract to serve as an assistant coach at . He had also been in contention for the position of senior coach at but declined to be interviewed after accepting the role at Carlton. Worsfold's appointment was controversial; Carlton's president John Elliott officially confirmed Worsfold had been engaged as assistant coach on "The Footy Show", two days before the club was due to play in a preliminary final. Carlton's senior coach David Parkin suggested the appointment had come "out of the blue", and it was later reported that he had threatened to quit as a result of the club's lack of consultation.