Faced with the common problem of dissatisfaction with the outcome of investments in information systems (IS), the IS community has long sought ways to improve information systems development (ISD). This paper reports on action research (AR) that sought to improve the effectiveness a UK university’s student record system (SRS), which had exhibited persistent problems. Critical systems thinking (CST) is seen to have value for ISD and was used to guide the AR. In the first stage of this research, the issues with the initial design of the SRS were identified to have largely resulted from insufficient elicitation of the underlying assumptions about, and perspectives on, complex organisational issues. The second stage centred on examining the situation from an “ought” perspective analysing what should be done and how, in order to develop creative solutions to the problems uncovered. The third stage involved recommending solutions to address the problems identified in order to improve the effectiveness of the SRS. Overall, the AR indicates that CST enables those involved to view the design and implementation of the SRS as a holistic system, critically reflect upon broad and complex human, technological and organisational issues from different perspectives, and thereby identify creative solutions. The main contribution of this research is in generating support for an ISD intervention guided by CST. The results of, and the understanding developed from, this intervention are likely to be relevant to the problems that frequently occur in similar situations.