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This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

A letter from the Headmaster Graham Smallbone to Bryan Waites at the Rutland County Museum regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson.

A letter from the Headmaster Graham Smallbone to Bryan Waites at the Rutland County Museum regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson and an article in This England.

An internal note from the Headmaster Graham Smallbone to Teaching Staff regarding the Spring term 1988 reports.

Two letters (A and B) from Graham Smallbone, Headmaster, and John Buchanan and Rev Terence Treanor asking Old Oakhamians to support the construction of the new library as part of the 1993 Development Plan. One letter was sent to O.O. who left in 1965 or earlier; one letter was sent to O.O. who left in 1966 or later.

Correspondence relating to John Barber's eightieth birthday and the Barber Archives.

Two notes from the Appeal Office to the Bursar (A) and the Headmaster (B), regarding the celebration of John Barber's birthday and the Barber Archive Room.

A memo (A) from John Lake, Appeal Director, regarding approaches to prospective major donors and enclosing a draft letter (B) to be sent out.

A group of letters related to the visit of the National Youth Chamber Orchestra to Oakham School in August 1993.