After his retirement, in 2007–08 Costacurta was a member of Carlo Ancelotti's coaching staff at Milan as a technical assistant, while earning his own coaching badges. At the end of the season, he successfully earned his badges and various Italian media reported that he was pursuing a managerial role of his own. However, he refused a position at Pisa offered by new club owner Luca Pomponi immediately after the completion of his takeover of the club, citing his need to remain at Milan in order to stay at home and take care of his son while his wife was on tour with the theater.