Persistent underperformance in the private sector of many African economies is often attributed to structural and governance deficiencies within enterprises. A comprehensive, longitudinal analysis of these specific challenges within Ugandan firms is lacking, particularly one that integrates business, economic, and psychological perspectives on organisational behaviour. This study aims to systematically diagnose the predominant structural and governance challenges hindering the performance and growth of enterprises. It seeks to identify the relative severity of these issues and their perceived impact on strategic decision-making and operational resilience. A stratified survey of senior managers and owners from a representative sample of Ugandan enterprises across sectors and sizes was conducted. The instrument employed Likert-scale and open-ended questions to assess perceptions of structural complexity, board effectiveness, transparency, and strategic alignment. Quantitative data were analysed using descriptive and inferential statistics, while thematic analysis was applied to qualitative responses. A critical finding is that 73% of respondents identified 'opaque decision-making processes and weak board oversight' as the most severe governance challenge, directly correlating with reported strategic inertia. Thematically, a psychological aversion to formalised structures was frequently cited as a barrier to implementing robust governance frameworks. The analysis confirms that deeply embedded governance weaknesses, compounded by behavioural resistance to formalisation, constitute a primary constraint on enterprise development. These issues undermine investment, innovation, and long-term strategic planning. Policymakers and business support organisations should prioritise interventions that build governance capacity, coupled with behavioural nudges to encourage structural formalisation. Enterprise leaders are urged to adopt graduated governance codes and invest in board training to enhance oversight and strategic clarity. Corporate governance, structural challenges, enterprise survey, strategic decision-making, behavioural finance, Uganda This paper provides a novel, integrated behavioural-financial dataset and analysis of firm-level structural pathologies, offering a diagnostic framework applicable to similar emerging market contexts.