The need to prepare future-ready graduates is now a major concern for educational programme leaders. But the world is changing at a rapid pace, professional and personal life environments are now more than ever volatile, uncertain, complex, and ambiguous. How can vocational and higher education institutions prepare learners for an unpredictable future? This paper presents an iterative design based research method, initiated in 2015. It explores the links between judgement, decision making skills, and reliability of organisations. Within engineering education and training environments, decision making skills are transversal and can be enriched by a multiplicity and variety of experiential learning situations. As a result of the applied iterative method, decision oriented learning situations can now be categorised in a VUCA rubric of perturbation. It permits educators to continuously reinforce reliability and learner proficiency throughout a curriculum.