This research is concerned with the evaluation of a Job Seeking Skills (JSS) programme at Manawatu Prison. Three groups of four JSS participants responded to questionnaire measures of self-esteem, social anxiety and fear of negative evaluation at pretest, posttest and at a six week follow-up. Self-esteem increased but no change occurred on measures of social anxiety and fear of negative evaluation. Subjects also took part in videotaped simulated job interviews at pretest and posttest. Subjects decreased their response latency, but no significant changes were noted on other behavioural measures. Despite this, subjects were rated as significantly more socially skilled and more employable at their posttest interviews. Improvements were also noted on ratings of appearance and question answering. Although subjects reported a decrease in anxiety in interview, ratings of anxiety by external raters did not indicate significant improvement.