Abstract
Many organisations still have difficulty obtaining value from their IT spend. The literature indicates that two ways of improving this situation is via better strategic business/IS alignment and the development of a dynamic IS capability. The literature has consistently shown that the development of either a high degree of alignment or dynamic capabilities is difficult for most organisations. It is argued that the development of these skills occurs within a complex, dynamic social system and has the characteristics of wicked problems and are poorly investigated using the dominant IS research paradigm. An inductive grounded theory study conducted to better understand the complexities of alignment is described. It used a coding family that emphasises the dynamics within a complex social system. The resultant emergent theory demonstrates why alignment has been an intractable problem for many organisations. Actors operate within a social system consisting of many feedback loops. The feedback system can hinder, or enhance, actors understanding of issues as well as limiting their ability to undertake courses of action that differ to past actions. The theory indicates that the level of alignment within an organisation is likely to be maintained over extended periods of time. It is then argued that the theory can also explain why many firms experience difficulties developing dynamic IS capabilities. A feature of wicked problems is that understanding the problem is an act of improving the situation. This research helps practitioners understand the wicked problem in which they operate. This, then, may allow them to alter the behaviour of their feedback system.