His diplomatic skills proved advantageous when serving with Montgomery. When Montgomery assumed command of Eighth Army in August 1942 he became Montgomery's chief of staff. In this role he was successful, and after the First Battle of El Alamein he was appointed the Eighth Army's Brigadier General Staff.
In February 1942 Dorman-Smith, now Deputy Chief of the General Staff at Middle East Command, recommended him for the position of Director of Military Intelligence, Middle East. In December 1940, on the recommendation of the Staff College's Commandant Eric Dorman-Smith, he was posted to the Joint Planning Staff of Middle East Command in Cairo where he also took on the role of secretary to the Commanders-in-Chief Committee. After Hore-Belisha resigned, de Guingand was posted to the new staff college at Haifa in Mandatory Palestine as an instructor. He served as Military Assistant to the Secretary of State for War, Leslie Hore-Belisha, from 1939 to 1940, in which role he had exposure to the most senior officers in the army and developed skills in diplomacy. Through the intervention of Montgomery, with whom he had formed a friendship with during their service together the 1920s and 1930s, he secured a nomination to 1935–36 course at the Staff College, Camberley. He served in India and Ireland, and was seconded to the King's African Rifles in Nyasaland from 1926 to 1931. A graduate of the Royal Military College, Sandhurst, de Guingand joined the West Yorkshire Regiment (Prince of Wales's Own) in December 1919.
He played an important diplomatic role in sustaining relations between the notoriously difficult Montgomery and his peers and superiors. Major-General Sir Francis Wilfred "Freddie" de Guingand, KBE, CB, DSO (28 February 1900 – 29 June 1979) was a British Army officer who served as Field Marshal Sir Bernard Montgomery's chief of staff from the Second Battle of El Alamein until the end of the Second World War.A més va ser un diplomàtic consumat, les habilitats del qual es demostraren vitals per mantenir les relacions entre el notòriament difícil Montgomery i els seus parells i superiors. Va ser un oficial brillant d'estat major, demostrat pel fet que Montgomery, que no demanava menys que la perfecció, el va mantenir com a cap del seu estat major durant dos anys i mig. El Major-General Sir Francis Wilfred de Guingand KBE CB DSO (28 de febrer de 1900 – 29 de juny de 1979), més conegut com a Freddie de Guingand, va ser un oficial de l'exèrcit britànic que serví amb el mariscal Montgomery des d'El Alamein fins a la rendició de la Wehrmacht a l'oest.
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