Studies whose focus is finding solutions to practical IT implementation issues / problems such as slow systems uptake and meaningful work improvement are few. This thesis describes how IS practitioners from government and the private sector, together with users came together to redesign the current Botswana ISD work practice in order to address this shortcoming. The result has been the incorporation of activity-based learning and reflection in current ISD practice. The study adopted Cultural Historical Activity Theory (CHAT) as the framework of analysis as well as the associated Developmental Work Research (DWR) methodology as the research method. An expansive learning cycle was stimulated through change laboratory sessions with participants from government and industry. The general research question for the study is: ‘How should ISD as a systemic work activity be carried out to facilitate effective learning?’ The four sub-questions the thesis focuses on are: ‘(1) What constitutes Botswana’s ISD practice or how is ISD currently practiced in Botswana? (2) What are the users and developers learning and is the learning effective? (3) How can current practice be improved in order to facilitate effective learning? (4) What do users and IS professionals learn when collaborating in the review and redesign of ISD practice?’ The study was qualitative in nature and data collection was based on interviews, archival data, observations as well as data from change laboratory sessions. Data from the change laboratory sessions was video-taped and later transcribed for analysis. Though I used CHAT as the main theoretical tool for analysis of ISD and learning, I also used additional theoretical concepts on learning to assist with the analysis and redesign of new practice. These are concepts relating to two types of learning that are found in any setting or environment i.e. conscious / learning conscious learning and unconscious / task conscious learning as well as concepts relating to reflection-on action. Analysis of learning in current Botswana ISD practice shows that current learning is not effective because it does not provide the right balance between conscious and unconscious learning. Current learning tasks are predominantly geared towards unconscious learning. The solution to this practical learning problem, which constitutes improvement to practice, is the incorporation of activity-based learning and reflection through the introduction of learning evaluation checkpoints throughout the ISD process. Furthermore, during the collaborative redesign sessions it emerged that: 1) learning was collective and distributed agency and 2) learning was expansion of the object in multiple dimensions. The study makes both theoretical and practical contributions. The theoretical contribution is through the application of learning concepts such as the two types of learning (i.e. conscious and unconscious learning) and expansive learning to the review, analysis and redesign of ISD practice with the participation of representatives from government and the private sector. In terms of the practical contribution, a new Botswana ISD practice model that incorporates activity-based learning and reflection has been designed, and findings from examination of the model suggest that it has potential to address current learning deficiencies and thus contribute to efforts of avoiding IS failures.