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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 David J. Woodhead, National Director of the Independent Schools Information Service, to Graham Smallbone regarding the passing of the Children's Act and its consequences in cases of abuse nationwide, enclosing an ISJC circular notifying of its implications. Three pages numbered A to C.

A letter from Graham Smallbone, Headmaster, to Dr G.B. Todd regarding a talk to the Liberal or General Studies Groups (Sixth or Seventh Forms), possibly related to current questions on child abuse, and new legislation concerning the Children's Act 1989. Three pages numbered A to C, and a sticky note numbered D.

A letter from Graham Smallbone, Headmaster, to R.C.G. following a Haileybury Group Meeting, suggesting that members of the C.C.F. would wear mixed uniform when travelling for security purposes.

A letter from Graham Smallbone, Headmaster, to R.M.P. regarding the accommodation for the Australian Gap Year students and their role within the school. Two pages numbered A and B.

A letter From Nigel Webb, Second Master, to the Housemasters and Heads of School regarding the poor behaviour of pupils in the town, smoking and general lack of respect in cafes and around hotels.

The items in this file are all letters sent or received by Jane Matthews on various pastoral issues at Oakham School or the planning of H.M.C. Co-Educational Group Meetings.

This collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

A letter from Gerry Lea to the Headmaster, Graham Smallbone, regarding sending back any items that belonged to Henrietta, and a letter from Graham Smallbone to staff asking them to return to her parents any items that belonged to Henrietta.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.