Case studies involving interviews with three Tasmanian dairy farmers and retrospective analysis of their benchmarking data were carried out to evaluate the pasture management learning process that occurred within the 20.12 Pasture Business Project. This paper describes the significant impact of coaching on farmers developing knowledge and skills, improving pasture consumption and cow health, and increasing confidence to further develop their businesses. Key learnings from the subsequent cross-case analysis about how and why the project was effective in promoting practice change were as follows: 1) Farmers were motivated to learn and were in the position to apply new knowledge. 2) Working one-on-one with a coach allowed farmers to incrementally build capacity from their unique starting point, and in relation to their specific farm setting. 3) The commitment to one-on-one coaching sessions motivated farmers to be disciplined throughout the learning process. 5) The learning process reached completion when farmers could confidently apply pasture management principles and adapt them as their farm business and environmental conditions changed.