Viskovatiy rose to the rank of dyak in 1553 during the time of Ivan the Terrible's intensive organizational activities.
In 1554, Viskovatiy was appointed a member of the boyar investigation committee regarding Prince Semeon Rostovsky's treason.
That same year, Viskovatiy had to appear before the ecumenical council of the Russian Orthodox Church because he had been influenced by Matvei Bashkin's heresy and had drawn other people into accepting it.
In 1563, Viskovatiy went on a diplomatic mission to Denmark to hold negotiations on Livonian affairs; that was the time when tensions between Denmark and Sweden were building up towards the Northern Seven Years' War, in which Russia did not take part, but was a very interested observer.
Viskovatiy was accused of his alleged intentions to give Novgorod to the Polish king and Astrakhan and Kazan to the Turkish sultan.