On being sacked by Aberdeen in November 1997 (after a 5–0 loss to Dundee United), Aitken turned his attention to coaching. In February 1998 he was appointed head coach of the Maldives national football team but resigned a month later over the poor facilities available to the team. After obtaining his UEFA Pro Licence at the Scottish Football Association's Largs training centre, Aitken went on to become a coach with Leeds United before rejoining former Leeds coach David O'Leary at Aston Villa.