The business landscape in Kenya is characterised by dynamic and often complex interactions between regulatory frameworks, market forces, and institutional governance. While quantitative studies have measured economic indicators, there remains a significant gap in nuanced, qualitative understanding of the strategic and governance challenges faced by firms over an extended period. This study aims to provide an in-depth qualitative analysis of the key strategic challenges and governance issues confronting businesses. Its objective is to identify and interpret the lived experiences and adaptive strategies of business leaders navigating this environment. A qualitative, multi-case study design was employed, utilising purposive sampling to select 24 senior executives from diverse sectors. Data were collected through semi-structured interviews and analysed using a thematic analysis approach to identify recurring patterns and insights. Analysis revealed a dominant theme of 'regulatory ambiguity' as a pervasive strategic challenge, directly cited by over 70% of participants. This ambiguity was found to complicate long-term planning and incentivise informal governance adaptations, often prioritising relational networks over formal compliance structures. The study concludes that strategic decision-making is profoundly shaped by perceived inconsistencies in the regulatory environment, leading to hybrid governance models that blend formal and informal practices. This has significant implications for organisational resilience and policy effectiveness. Policymakers should focus on enhancing regulatory clarity and consistency. Business support organisations are advised to develop programmes that help firms build strategic agility and formalise adaptive governance practices without compromising compliance. Strategic management, corporate governance, regulatory environment, qualitative research, business challenges, Kenya This paper provides a novel, longitudinal qualitative dataset capturing executive perspectives on strategic adaptation, offering a granular understanding of how governance is practised in response to environmental complexity.