It is known that the work of headteachers is demanding. Observation, diaries and logs completed by headteachers show a relentless, complex and emotionally demanding workload. What can be learned about headship from how new headteachers spend their time, and perhaps as importantly, what can new headteachers themselves learn? This article draws upon data, including that derived from observation, from a small-scale qualitative study of new headteachers in large cities, funded by the English National College for School Leadership. It examines how headteachers spend their days, the challenges faced and the value of being observed. It argues that the learning about leaders and leadership from observation has been considerable. A new observational classification is outlined. An analysis of the headteachers' day provided insights into the things that mattered most, the challenges currently faced and how they were acting as learning-centred leaders. The other main form of learning from observation was for the research participants themselves. Gaining feedback and reflecting on their actions and use of time as school leaders was deemed to be very helpful. The article concludes by suggesting that being observed has the potential to be a powerful form of leadership development.