This exploratory study set out to understand how to 'design' change in this complex interconnected world - Whole Systems Designing (WSD). The purpose of this study is to (1) understand WSD skills; (2) prototype tools and methods to teach and measure them. The literature on systems theory, design thinking and change leadership is reviewed to identify and present 18 WSD skills in principle and practice. Also, a framework for Whole Systems Change is offered as a first step for teaching these skills. A design study developed WSD card-set and evaluated its efficacy through a focus group study. The participants found it useful for explicitly discussing their personal design process. A research study which used network methods to map the learning behavior of 60 students found that educational background predisposes students to learn different skills and students from the same educational background and year in school have similar concept maps.