This report explores the value of the design approach in policymaking, specifically applied to the policy brief "Straffen op Maat". The aim is to offer insights into the potential of an iterative, problem-driven methodology for addressing complex societal challenges, often referred to as wicked problems. I went through seven steps, each of which altered the perspective on the problem statement and influenced the concept. Below, I will briefly explain these steps, which correspond to the chapters in the report. 1. Reducing recidivism is a complex and persistent problem. The judiciary cannot fully focus on a single goal, partly because it must balance its four primary objectives, but also because it needs to remain cost-effective and account for the diverse expectations of society, which often conflict with measures aimed at reducing recidivism. With limited resources, the problem owner must cater to multiple stakeholders. As a result, solutions must be immediately appealing to all involved, complicating research into the problem space. 2. The paradox that is dominant in the problem is the demand for more maatwerk (greater time investment) in a system that is overloaded and therefore less capable of delivering it. This points to the need for a solution that can also simplify, structure the problems at hand. 3. By examining the immediate context, I arrived at the following reformulation: "A system that punishes too harshly creates a negative spiral." This perspective also opens opportunities for systemic change. "Too harshly" is defined here as stricter than what is scientifically ideal for minor offenses. A negative spiral arises because harsher punishments lead to higher recidivism rates, which in turn create public unrest and result in demands for even harsher punishments from society. 4. In the Field section, I investigated different stakeholders in the justice chain and how the system function. From this analysis the revision of the problem statement was: How can a judge deliver maatwerk if there is no direct feedback loop on previously delivered maatwerk? (How can this be aligned across a chain that includes numerous actors and organizations with varying ways of operating?) 5. The absence of a feedback loop prevents the system from learning from the maatwerk applied in sentencing recommendations. 6. which serves as the foundation for a solution concept. The constructed frame can be encapsulated in the following question: “What if we create a reflective conversation following punishment that fosters reflective learning for both parties? (delinquent and state)” How can punishment be evaluated on an equal footing, enabling both parties to gain meaningful insights from the evaluation? 7. I tested the frame with experts at the ministry, a concept was developed proposing two reflective conversations: one immediately following the punishment and another scheduled six months to a year later. Both conversations are conducted via phone, preceded by an explanatory WhatsApp message. These conversations are preferably facilitated by lived experience experts—individuals who bridge the gap between the system and its clients. Data collected from these conversations should be used to evaluate and refine current maatwerk solutions.