This chapter introduces the Second Chances Framework, a practice-informed tool for evaluating whether individuals who have committed ethical wrongdoing in organizational settings should be granted another opportunity. Drawing on 12 years of discussions with Executive students, the framework was developed from real-world cases shared by experienced professionals across diverse sectors. Five key factors—precedent, reparation, trust, transparency and fairness—emerged repeatedly in these cases and form the foundation of the framework. Each factor is presented with guiding questions to aid structured reflection and ethical judgment. The framework is intentionally flexible: the five elements are interconnected and non-hierarchical, with different cases giving greater weight to some factors over others. While the framework is not based on formal coding, it has been iteratively refined through student and co-teacher feedback and critique. The chapter positions the framework within both normative and descriptive ethics and explores how systemic and situational contexts influence decisions about second chances. It argues that ethical legitimacy depends not just on outcomes, but on transparent and principled decision-making processes. The chapter lays the conceptual foundation for the subsequent detailed exploration of each framework element in later chapters.