When Jean-Philippe Courtois took control of Microsoft’s global sales, marketing and operations in 2016, reporting directly to CEO Satya Nadella, he realised that he needed to lead the organisation away from an “inspection culture” towards a culture of learning and coaching. After a first phase of transformation focused on giving Microsoft’s sales teams the right skills to accompany customers as they moved to the cloud, a second phase aimed to fundamentally transform their behaviours and mindsets. The case study describes how Courtois and his leadership team envisioned and executed a culture change effort consisting of harnessing technology to generate insights into employee and partner work patterns and enabling coaching conversations that would help staff more effectively leverage their time to serve customers and attain key results.