This paper advocates for the explicit articulation of the needs for programs to engage in external and internal scanning within an educational context, to strengthen each program’s positioning in responding to changes in its operating environment in a more timely and effective manner. It noted that the 12 CDIO Core Standards, in particular Standard 1 and Standard 12, did not state explicitly the need for Program Chair to undertake such exercises. In addition, Standards 9 and 10 also did not made clear that this should be a core competency of Program Chairs. This paper suggests that Program Chairs can learn from strategic planning management in the business world, using tools such as STEEP Analysis and SWOT Analysis. STEEP is the acronym for the five drivers of change that can affect an organization and its operations, namely Social, Technological, Economic, Environmental, Political; and SWOT stands for the acronym Strengths, Weaknesses, Opportunities and Threats that the organization is facing. In addition, due to the complex nature of education, with many stakeholders often with competing demands, a tool for analysis the relationship between these stakeholders is also needed. This paper firstly provides a brief introduction strategic planning in the educational context, followed by the use of STEEP Analysis and SWOT Analysis. It then shares the use of STEEP Analysis and SWOT Analysis alongside the CDIO Self-Evaluation process by way of 2 case studies for the Diploma in Chemical Engineering (DCHE): one in introduction of chemical product design (in 2007) and another on impact of Industry 4.0 on chemical engineering education (in 2018). The paper then proceeds to discuss a key learning point from the latest review of the DCHE curriculum initiated in 2020 to enhance coverage of sustainable development, which is the need to make sense of sustainability issues. This paper further posits that today’s educational system is itself a complex system and efforts towards Education for Sustainable Development needs a more systematic approach to complement the CDIO Self-Evaluation in analyzing interactions and relationships between various change drivers and key stakeholders. To this end, the paper proposes one explores the Cynefin Framework, which had been used as a tool for sense-making when analyzing complex systems in various contexts. Lastly, this paper discusses the relative merits in the CDIO Framework in formalizing the use of external and internal scanning and developing competency for Program Chair in this area.