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Considering Systems Thinking (ST) as a cognitive skill can create greater acceptability of and openness to the discipline from practitioners and researchers outside operations research and management science. Rather than associating ST with frameworks and methodologies, ST as a cognitive skill can help popularize and democratize the discipline. This paper highlights how the conceptual lens of Holistic Flexibility can help practitioners deploy ST as a cognitive skill without the application of any traditional systems methodology. Holistic Flexibility is defined as the dynamic interplay between a state of mind that has the ability to absorb systemic complexity and a state of practice that has the ability to embrace flexibility, both in intent and in form. Through two case-studies, discussions in this paper highlight how Holistic Flexibility can serve as a conceptual lens for systems practitioners. The case-studies demonstrate the importance of a practitioner’s ability to seamlessly manage and work with multiple variables, stakeholders, and factors to deliver responsible outcomes with the aid of learning loops. The main contribution of this paper lies in the case-studies and analyses presented that provide use cases for Holistic Flexibility in ST, which will help address recent calls in the discipline for ST to be considered as a cognitive skill.