In this chapter, Anna Sheather helps coaches to get started with coaching with art and to overcome some of the biggest barriers that coaches can put up to working in this way. There are suggestions for helping coaches build confidence in their own creativity as well as some hints and tips around building confidence in their own practice of coaching with art. In addition, Anna provides advice on being prepared for a coaching-with-art session and for getting started with materials, including guidance on putting a starter pack together and making a portable pack for coaching on the move.