In this chapter, we explore the need for a structure that encourages flexibility and tailoring to the individual. A few well-known models from the career coaching, guidance and counselling fields are considered, including GROW, CLEAR, the skilled helper and SIM. Taking common features from these and adapting the language to reflect the field of career development, we arrive at the Creative Career Coaching Model. This model emphasises the need for a strong contracting stage that ensures client understanding of and commitment to the process. There is also a clear emphasis on deep exploration of career management strengths, issues and needs, and gentle challenging to unearth and address high-leverage issues. We explore how the model can be used flexibly to meet client needs, allowing for artistry on the part of the practitioner. The model provides a secure structure that allows the coach to introduce varied tactics to meet the client’s needs.