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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 collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

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.

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

Two letters between Roger Blackmore and Alan Grieve on various matters, such as the last OSEL meeting, the new brochure for the Medical Congress and OSEL accounts.

A letter from Roger Blackmore to Alan Grieve regarding the latest minutes of OSEL meeting and discussing five points relating to catering.

A letter from Roger Blackmore to Alan Grieve regarding the minutes of an OSEL meeting and the publicity for the upcoming Chess Congress.

A letter from Roger Blackmore to Alan Grieve regarding the agenda for the next OSEL meeting and enclosing notes and initial comments on the questionnaires, accommodation, courses and other activities. Six pages A to F.

A letter from the Headmaster Graham Smallbone to T.M. Reay, Mrs Wheway, Roger Blackmore and the Housekeepers, containing the minutes of a meeting regarding OSEL, conferences and support to house staff. Two pages A and B.

A letter from Alan Grieve to Roger Blackmore regarding the minutes of OSEL meetings and raising two points on Activity Holidays and Computing courses. Two pages A and B.