The burden of diabetes and obesity is increasing worldwide, indicating a need to find the best standard for diabetes care. The aim of this study was to generate a theory grounded in empirical data derived from a deeper understanding of health care professionals’ main concerns when they consult with individuals with diabetes and obesity and how they handle these concerns. Tape-recorded interviews were conducted with seven groups and three individual members of a diabetes team in an area of western Sweden. The grounded theory (GT) method was used to analyse the transcribed interviews. A core category, labelled Balancing coaching and caution and three categories (Coaching and supporting, Ambivalence and uncertainty, and Adjusting intentions) emerged. The core category and the three categories formed a substantive theory that explained and illuminated how health care professionals manage their main concern; their ambition to give professional individualised care; and find the right strategy for each individual with diabetes and obesity. The theory generated by this study can improve our understanding of how a lack of workable strategies limits caregivers’ abilities to reach their goals. It also helps identify the factors that contribute to the complexity of meetings between caregivers and individuals with diabetes. © 2011 I. Svenningsson et al.