Smith, 36, who also played for Gillingham, had a lengthy spell at Woking and more recently managed Blue Square South Welling United and has been turning out for Bromley as a player.
O'Shea, 41, played over 100 league games for the Gills.
He started his career at Tottenham and has coached the Millwall academy.
Woodward has wasted no time in strengthening his squad with the loan signing of Dagenham & Redbridge striker Jamie Taylor.
Taylor has played for Aldershot Town, AFC Wimbledon and Woking, and is on a month`s loan at The New Recreation Ground.