When considering organization strategy-making and execution from a learning perspective, the role of conversation and engagement is of critical importance, yet little research has been conducted in this area. Recent publications have suggested an increasing role for conversation and dialogue in strategic planning processes. The present study provides initial validity and reliability scores of an instrument for measuring individual conversation quality and engagement skills in a strategic planning context. Participants were managers (n = 204) from four organizations. Results indicate an instrument with highly accurate and consistent measurement scores. Implications for practice and future research are briefly discussed.