Chesswas was employed by the Luganda Language Board as a teacher of Luganda when, in 1949, the Government for the Uganda Protectorate began to offer free courses in Luganda to any officer wishing to take up the study.
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Chesswas spent 19 years in the education service of Uganda, predominantly as Provincial Education Officer, Buganda, and finally as Officer in Charge of the Educational Planning Unit within the Ministry of Education.
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Chesswas cites Sir Apolo Kagwa's Engero z’Abaganda and Michael B. Nsimbi's Olulimi Olugand as his major sources, and acknowledges Nsimbi as his primary aid in developing the text.