Research has long established that the most effective strategy for reducing reoffending is to develop collaborative relationships with service users. Practitioners need to exhibit empathy, mutual respect, and an appreciation for the life, perspectives, and needs of service users. However, the balance between trusted confidante, and enforcer is a difficult one to achieve. With this in mind, the London Probation Trust (LPT) developed the role of engagement worker in order to provide practitioners with another resource to be utilised towards their attempts to establish successful working relationships with their service users. The engagement workers are former users of the Probation Service themselves - a life experience that allows them to successfully engage current service users, in a way that practitioners are not always able to do. Furthermore, in addition to supporting individuals to change, the experience of being an engagement worker may contribute to the engagement workers’ own desistance. Following a year of the engagement worker experiment, the project was evaluated by the LPT (now London CRC) research analyst. This chapter asks whether employing ex-offenders in this way can enhance engagement and improve outcomes.