This guide outlines the Red Teaming process, which is a specialized form of security testing that simulates real-world threat scenarios to evaluate an organization's security posture. It emphasizes the importance of planning and preparation to maximize the effectiveness of Red Team engagements. The document details how Red Teaming differs from traditional penetration testing by focusing on specific attack objectives rather than merely identifying vulnerabilities. It describes the value of Red Team operations, which provide a full attack narrative from an adversary's perspective, revealing weaknesses and blind spots in security programs. Key planning questions are presented to help organizations clarify objectives, define scope, and align stakeholders before engaging in Red Teaming. The guide also introduces frameworks for planning future Red Team operations tailored to an organization's unique security posture. Overall, it serves as a comprehensive resource for security leaders aiming to enhance their detection and response capabilities against real-world threats.