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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 reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

Minutes of an OSEL meeting held on 25 October 1983 at the Headmaster's house. Contents: Minutes; Matters arising; Medical Congress, January 1984; Chess Tournament; Other April events; Activity Holidays 1984; Computer Weekends; Catering budgets and menus. Seventeen pages A to Q.

A memo from Roger Blackmore to Graham Smallbone enclosing a report on OSEL's activities, and estimated income and expenditure. Four pages A to D.

A report on OSEL's Activity Holidays in the year 1986-1987, including payments and balance sheet.

A letter from Roger Blackmore to Andrew Barrett regarding his remaining on the OSEL board.

A letter from Alan Grieve at Taylor Garrett to Simon Schanschieff regarding the content and objectives of the Activity Holidays for 1987.

A letter from Roger Blackmore to Alan Grieve regarding attending a meeting of delegates from companies marketing Activity Holidays and OSEL being represented in a sub-committee.

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

A memorandum from T.M. Reay. Bursar, to Graham Smallbone, Headmaster, regarding the the financial position concerning any catering in support of the Oakham Festival.