This chapter provides a reflection on how important a robust coaching contract is for any piece of coaching work. There is a case study of a best practice coaching conversation, where the client invites a blurring of boundaries away from non-directive coaching. The contract has equal significance in the organisational sponsorship of coaching work. Another case study illustrates the pitfalls of not being well prepared. It highlights the risk of naively believing one’s competency in coaching is sufficient and the consequences of not taking account of the context of the organisation. The piece reflects comparisons of capability and affirms that there is a progressive journey to be taken from novice to master coach.