The effects of content and timing in the presentation of structuring were assessed using group therapy clients at a university counseling center. Using group development theory, two content areas, anger and intimacy, and two developmental periods, storming and norming, were identified for study. Handouts describing these contents were matched (i.e., anger handout given during the storming phase) or mismatched (i.e., intimacy handout given during the storming phase) with the group's developmental phase. Matched Content X Timing interactions resulted in more comfort in dealing with intimacy, more appropriate expressions of intimacy and anger and fewer inappropriate expressions of intimacy, more congruence between self-ratings and other ratings of interpersonal style, and less interpersonal rigidity. The predicted Content X Timing interaction did not occur for comfort in dealing with anger, fewer inappropriate expressions of anger, and self-rated change. Implications for research and practice are discussed. 363