Ambassador Checchia started his diplomatic career in 1978 and later attended the Diplomatic Training Course at the Istituto Diplomatico. He was first assigned as Assistant Attaché to the Ministry of Foreign Affairs (MFA), Directorate General for Economic Affairs, Middle and Far East Countries Desk, and later to the Press and Information Services.

He was then posted to Mexico City until the end of July 1985. He was appointed Consul to France in the city of Bastia on 29 July 1985 and then assigned to Ankara on 15 November 1987 as First Secretary, an office he maintained until his promotion to Counsellor on 1 May 1988.

Mr. Checchia returned to the MFA in 1990 and was assigned to the Directorate General for Political Affairs, CIS and Central/Eastern European Countries Desk, where he remained until 3 September 1995 also as Deputy Desk Director. In this capacity, he regularly participated in the meetings of NATO and EU working groups dealing with former Soviet Union countries and related issues.

He was the Italian representative within the EU Working Group for Enlargement (and Chair, during the Italian Presidency in 2003), where he contributed to the preparation of the 2004 accession of ten Mediterranean, Central and Eastern European countries. Likewise, he represented Italy in the EU Working Group on former CIS and Eastern European Countries and related EU-funded assistance programmes (TACIS Programme).

Posted for the second time to the Italian Embassy in Ankara on August 1999 as Minister-Counsellor and Deputy Head of Mission. In 2001, he returned to Rome following his appointment as Diplomatic Advisor to the then Minister of Productive Activities, a position he held until 1 October 2006.

From 2006 to 2010 he served as Ambassador of Italy to Lebanon. At the end of his mandate, Mr. Checchia returned to Rome and was appointed Special Envoy of the Italian Minister of Foreign Affairs for Afghanistan and Pakistan. Mr. Checchia took up his duties as the Diplomatic Advisor to the Minister of Defence in June 2011.

In 2012, he was named rank Ambassador by the Council of the Ministers. Appointed Permanent Representative to the Atlantic Council in 2013. Ambassador to OECD from 2014-2016.