Successful penetration testing commences well in advance of any technical exploitation efforts. This chapter emphasizes the essential preparatory phase of penetration testing, highlighting the significance of planning, governance, risk management, compliance, and environmental factors. It emphasizes that inadequate scoping and a lack of legal awareness might result in operational disruptions, ethical breaches, or legal repercussions. This chapter examines the incorporation of governance, risk, and compliance (GRC) principles into penetration testing activities to guarantee alignment with company goals and regulatory mandates. Furthermore, it delineates procedures for establishing a precise and thorough scope that aligns with client expectations, technical limitations, and legal requirements. The chapter emphasizes the importance of professionalism and ethical responsibility by assisting practitioners in formulating a personal code of conduct. Upon concluding this chapter, readers will possess the essential information and documentation methodologies required to perform penetration testing activities in a legal, organized, and ethically responsible manner.