Throughout our careers, Probation staff have presented differing attitudes and approaches towards working with women. To some, it is actively avoided, and it is quite common to hear from practitioners that, ‘working with one woman is like working with ten men’. Yet to others, it is the part of the job they most enjoy. Whilst practitioners' attitudes towards working with people having certain convictions is well investigated (i.e. Lea, Auburn and Kibblewhite, 1999), the phenomenon of attitudes towards working with women is hardly discussed. This study sets out to fill this gap by investigating the self-reported reasons for these differing attitudes and understand whether they were based on personal beliefs or external factors that could be changed through a shift in the organisation. Employing a two-staged, mixed method approach, we first conducted a staff survey across the Midlands probation region and then spent time speaking with two teams of staff who work exclusively with women, in focus groups.