After retiring as a player, Barry moved into management, taking the reins at Dunstable Town, Bedford Town, Maidstone United, Southend United, Barnet, Birmingham City, and most recently, Peterborough United. He is currently the Director of Football at Peterborough United.
Barry’s often unpredictable approach to the transfer market earned him a reputation for making bold and sometimes erratic decisions, leading to Birmingham City fan Jasper Carrott humourously remarking that Fry was “probably trying to sort out the unemployment problem single-handedly”. One of Barry’s most memorable moments came in a 1995 match against Huddersfield Town, when after Birmingham City took the lead, Barry leapt from the dugout, running the length of the touchline with his arms flailing like a windmill before jumping into a commentator’s booth—a spectacle rarely seen when matches weren’t televised.
Known for his attacking style of football, Barry’s teams were often thrilling to watch, although his tactics sometimes led to as many goals conceded as scored.
Now a regular figure on the after-dinner speaking circuit, Barry’s vibrant personality and entertaining stories from his football career continue to captivate audiences, making him one of the most sought-after speakers in the industry.