In 1887, upon the death of the schools' principal, [[John Collins Covell]], Gilkeson was selected by the Board of Regents to serve as principal of the institution.refrefref He left his lucrative law practice and accepted the position under the condition that he serve as an interim principal while the Board of Regents sought a more suitable candidate to build upon Covell's initiatives and reforms.refref Gilkeson believed that only administrators and educators fluent in [[sign language]] should be appointed to serve in the School for the Deaf, and during his tenure as principal, he found that personnel who relied on [[Language interpretation|interpreters]] did not receive "satisfactory results".ref During his tenure, the position of principal included the roles of [[clerk]], [[Bookkeeping|bookkeeper]], , and final arbiter of matters in the classroom.ref While he lacked special training for the position, Gilkeson's business experience allowed him to run the schools in an economically efficient manner, which pleased the schools' Board of Regents.ref