Chesney served as a royal justice in Lincolnshire during his bishopric, and maintained a close relationship with his nephew, Foliot. He was also an early patron of Thomas Becket, and gave the young cleric an office in his diocese early in Becket's career. Although shown favour by King Stephen, including the right to a mint, Chesney was present at the coronation of King Henry II in 1154 and went on to serve Henry as a royal justice. Around 1160, Chesney became embroiled in a dispute with St Albans Abbey in the diocese of Lincoln, over his right as bishop to supervise the abbey. The dispute was eventually settled when the abbey granted Chesney land in return for his relinquishing any right to oversee St Albans.

Chesney was active in his diocese; more than 240 documents relating to his episcopal career survive. They show him mediating disputes between religious houses and granting exemptions and rights in his diocese. Chesney bought a house in London to serve as an episcopal residence, constructed an episcopal palace in Lincoln, and founded a religious house outside the city. He died in December 1166, probably on the 27th, and was buried in Lincoln Cathedral.