In 2009, he enrolled in a 'Leaders in Development' course at the John F. Kennedy School of Government, Harvard Kennedy School, Harvard University, Cambridge, Massachusetts, U.S.A., and in 2011, enrolled in a Master of Business Administration (MBA) program at the University of Ilorin, Kwara State.
The following year in 1999, he was appointed s special assistant to the federal minister of Finance, Alhaji Jubril Martins Kuye (JMK), and served in this position until 2003.
Ishola returned to Ogun State in 2003 to serve as Secretary to the Government under the administration of Governor Gbenga Daniel.
[5] Four years later, he returned to Abuja to serve as substantive Minister for Mines and Steel Development on 26 July 2007 following his appointment by President Umaru Musa Yar'Adua.
[7] However, he returned to government in 2020 following his designation as a non-career ambassador by President Muhammadu Buhari on 1 July 2020 and his subsequent posting on 13 January 2021 as Nigeria's High Commissioner to the United Kingdom.