In previous research, “wicked problems” are described and defined as a combination of complexity, uncertainty, and diversified values, between different actors. The literature also proposes that within wicked problems there are no simple solutions. Based on interviews with 12 university managers and leaders in Sweden and Britain, the results of this study show that teaching and teaching quality in higher education are areas with wicked tendencies, and often with an ambition to be solved by rational solutions. This paper consequently aims to identify how managers and other leaders in higher education, at different organizational levels and with different roles – related to teaching and learning quality – discuss and handle improvements and managing of teaching and learning. The paper also shows how clumsy solutions are part of leadership in today’s higher education.