A structured planning framework document that guides red team exercise preparation with emphasis on blue team development and learning outcomes. The document provides methodological guidance for red team planning by contrasting against approaches that prioritize blue team engagement and skill development. It focuses on avoiding punitive methodologies that could negatively impact team morale or organizational cohesion. The framework includes evaluation criteria to assess the thoroughness of red team planning for maximum blue team benefit. It identifies counterproductive motivations that should be avoided, including attempts to prove organizational vulnerabilities, demonstrate technical superiority, or conduct intimidating demonstrations. The document emphasizes stakeholder engagement and leadership sponsorship as critical components for successful exercise outcomes. It provides guidance on establishing proper follow-up mechanisms and maintaining momentum from exercise learnings. The planning approach specifically excludes vulnerability enumeration exercises and basic detection mechanism testing, instead favoring constructive engagement methods that promote collaborative learning and improvement.