Given the complexity of the phenomena comprising wisdom in practice, approaches to understanding how it might best be investigated need to be carefully considered and justified. This includes the kinds of data to be gathered, from whom and for what purposes, and how these data are analysed, conclusions drawn and deductions generated. Consequently, this chapter sets out the description of several approaches and justification of the overall method and procedures used for data gathering and their analysis in this book. The analysis was conducted in three distinct ways drawing upon different but reconcilable orientations and approaches. There was, firstly, a theory-driven thematic abductive analysis was undertaken to see how the data aligns with an existing construct of wisdom, the Holistic Wisdom Model. This involved using its core concepts and premises, while also comparing and seeking features that do not comply with that construct. Then, the second line of the analysis was undertaken using a praxeological approach to discourse organisation. The approach taken combined principles of discourse analysis with a conceptual framework for investigating the relations between discourse and action through a range of interconnected theoretical perspectives. Lastly and thirdly, a hybrid approach of inductive and deductive thematic analysis of the interview data was conducted. This analysis was conducted to offer a fresh approach to considering what constitutes wisdom in practice, its learning, bases for collaboration and its relationship with individuals’ personal values, using a detailed analysis of their utterances.