Theoretical constructs to explore neurocognitive management of challenging behaviour in young people are inherently fraught with the difficulty of what exactly is to be measured that is acceptably benchmarked against standard mechanistic scientific inquiry. Indeed, this identifies the potential for a new scientific paradigm to be developed that explains the links between complex brain systems and functions, the development of the mind and adolescent challenging behaviour. The imperative lies in overcoming the strictly linear nature of some of the current scientific inquiry methods embracing instead, tools that can measure the non-linear, unexpected and emergent features of change. These changes are elicited through the interaction of the brain and human environments, sometimes manifesting in chaotic and challenging behaviour. The objective of this article is to explore the subtleties of complexity theory, to determine an essential lead to a non-linear way of measuring challenging behaviour in adolescents. The brain is a complex system and CT provides, here, the framework for understanding the dynamic and often non-linear neural activity that shifts in response to changes in an individual’s environment. I pose the question; Exploring CT as an underpinning theoretical framework, is it demonstrated that there are methods of measuring the non-linearity of an individual’s challenging behaviour, in a way that meets the expectations of sound scientific inquiry? The method used is an exploratory review and is addressed in two parts. The first is how to explain challenging behaviour in a neuro-informed state of complexity and the second is whether it is possible to use Complexity Theory as an exploratory framework for determining the non-linear characteristics of challenging behaviour. The article concludes with suggestions that Complexity Theory is an evolving theoretical construct primed to advance a more in-depth understanding of the non-linearity of challenging behaviour. As such, Complexity Theory has the potential for exploring a new paradigm of scientific inquiry.