While Weekes was never coached as a young player, he was appointed a Barbados Government Sports Officer in 1958 and found great success as a coach, encouraging young players to obey their instincts and develop their own style. Such was his success, Weekes was appointed coach of the Canadian side at the 1979 Cricket World Cup. Additionally, Weekes served on the executive of the Barbados Cricket Association for many years and helped develop many leading Barbadian players, including Conrad Hunte and Seymour Nurse, both deeply influenced by Weekes. Weekes also found time to work as a television and radio cricket commentator, known for his acerbic wit and deep knowledge of the game and began to play Dominoes and Bridge competitively, representing Barbados in regional Bridge championships. "The New York Times" referred to his style as "aggressive".