He joined the architectural firm Van Ginkel Associates as Chef de Bureau, working on the development of Downtown Montreal and Meadowvale, Ontario, a new town community for the newly incorporated City of Mississauga.
[3] During his time at IOR, he was instrumental in developing the use of Strategic Choice Theory (a dynamic socio-technical approach to planning and decision making) to help diverse groups experiencing multi-faceted challenges reach consensus.
The company collaborated with an international network of specialists working on the processes of planning, conflict resolution, and strategic choice, while providing services in action research, training, and facilitation.
[6][7][page needed] Hickling was employed by the Environment Directorates of the Dutch,[8] German, French, Italian, Latvian,[9] Estonian, Hungarian and British Governments, the OECD, and the European Commission,[10][page needed] to facilitate the solving of complex problems at the highest levels by enabling politicians, professionals, managers, industry representatives, and special interest groups to work together interactively.
Hickling was also heavily involved in the private sector, working for large and small companies including British Nuclear Fuels, Direct Rail Services, IBM, Cable and Wireless, Shell, Thames Water, EBRD, and Hamersley Iron.
In addition, Hickling wrote numerous papers and made many contributions to books and journals on the subject of planning and strategic choice.
Both companies designed and produced add-on products for Fantasy Role-playing games (FRP) such as Dungeons & Dragons (D&D) and RuneQuest.