Behavioral change of incarcerated boys is influenced by the alliance with the group workers who support them. This alliance is partly determined by the extent to which both the needs of group workers and boys are being fulfilled. The objective of this research was to explore the views of incarcerated boys regarding their relationship with group workers. Q methodology was used, a combination of qualitative and quantitative methods. Respondents ranked statements on behavior and treatment of group workers. Analysis of these individual Q sortings resulted in four preferences: (A) anxious and willing, (B) rebellious and defensive, (C) autonomous and indifferent, (D) dependent and approachable. Results show that needs regarding interaction with group workers are diverse and ask for different approaches. The understanding and awareness of these preferences offers tools for establishing a working alliance and stimulate the boys’ readiness to change.