Whilst a positive working relationship has been recognized as a ‘powerful vehicle’ for offender change (NOMS, 2010), little is known in respect to how powerful a positive working relationship can be for probationers and the impact it may have upon their lives. From considering the ‘experience’ of a working relationship, this study evaluated ‘what worked’ for probationers by drawing from the successes and failures within a relational context. The study also explored the impact of these relationships upon the probationers, both at the time of the relationship and once it had ceased. Seven probationers were involved in this collaborative study, assisting in the design and analysis of the study, as ‘experts’ in probation relationships. The results tentatively suggested that certain characteristics (acceptance, respect, support, empathy and belief) enable a positive relational climate to exist that has a powerful impact upon the probationer, their beliefs and their behaviour. Conversely, if the probation supervisor (PS) fails to demonstrate these characteristics, a ‘toxic’ environment for change is more probable and could lead to greater risk of offending.