Our Forces face operating environments of ever increasing complexity. In his opening address to ITEC 2010, Lt Gen Newton, Commander Force Development and Training in the British Army, characterised the complexity of contemporary warfare as a "wicked problem". This complexity places ever increasing demands on the training environments within which our Forces train. At the same time, budgetary and environmental pressures necessitate increasing reliance being placed on synthetic training environments, with the reducing availability and viability of live training. This presents a significant challenge to the training community to ensure that training environments are correctly specified so that effective training environment options can be developed. Whilst the principles of Instructional Systems Design/the Systems Approach to Training have a well established tradition within NATO Forces, the underpinning analytical techniques are predominantly focused on individual training. In the published literature there are relatively few techniques that address the issues of collective training (the training of teams and teams of teams). This paper articulates a novel approach to the development of training environment specifications appropriate to collective training. The first part of the paper describes a novel model of team training which captures how teams perform tasks (derived from a synthesis of team performance models), and includes new representations of both team task environments, and of how training is overlaid onto team task performance. The second part of the paper demonstrates how analytical techniques from the human factors and software engineering domains can be adapted and integrated with some new representations to facilitate the analysis of collective training tasks within the framework of the team training model, such that a training environment specification can be incrementally developed and checked throughout the training analysis process.