The persistent underperformance of domestic enterprises, despite macroeconomic growth, suggests deep-seated structural impediments. Existing analyses often focus on isolated factors, lacking an integrated diagnostic framework. This article develops a novel theoretical framework to systematically diagnose the interconnected structural challenges constraining enterprise development. It aims to categorise and model the relationships between institutional, financial, and managerial barriers. The framework is constructed through a synthesis of institutional economics, behavioural finance, and management theory. It employs a systems-thinking approach to model causal relationships and feedback loops between identified challenge domains. The framework posits that a dominant theme is the self-reinforcing cycle between weak contract enforcement and short-termist managerial behaviour, which undermines long-term investment. It identifies access to patient capital as a critical, yet proportionally scarce, enabling factor. The proposed framework provides a coherent diagnostic tool for analysing enterprise ecosystems, moving beyond descriptive lists of challenges to model their systemic interactions. Policymakers and development agencies should apply this framework for targeted, multi-level interventions. Future research should operationalise the framework for empirical testing and comparative analysis across similar economies. structural challenges, diagnostic framework, enterprise development, institutional voids, behavioural finance, systems thinking This article's novel contribution is a synthesised diagnostic framework that models the dynamic interplay between institutional, cognitive, and financial constraints, offering a new tool for systemic analysis and policy design.