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This paper outlines key aspects of a maximally informative and manageable ‘assessment topology’ for conducting an operational and/or mission assessment in a complex environment. This examines the structure and relationships between lines of operations (LOOs), measures, and indicators at various organizational levels. The proposed methodology handles the trade-off between complexity and tractability in a flexible and efficient way. The model is sufficiently generic for adaptation to a wide range of environments, as opposed to any particular mission. There are few key points that can be made on the basis of the authors’ experience with the assessment in Afghanistan. 1) The complexity of the assessment framework should reflect the complexity of the assessed environment, in particular of its organizational structure; 2) The assessment framework should reflect multiplicity of the temporal and geographical scales present in the assessed environment; 3)High-level assessments need to include more than a simple roll-up of lower-level assessments, an iterative combination of a top-down and bottom-up assessments might be required; and 4) When combining partial assessments into an overall situational picture, weighted averages should be avoided if possible, unless they are used to combine the same type of variables.