The strategic and governance landscape for enterprises in Kenya has undergone significant transformation, influenced by regulatory reforms, technological adoption, and evolving socio-economic pressures. A nuanced understanding of the persistent and emergent challenges faced by business leaders is required to inform both managerial practice and policy. This study aims to identify and analyse the principal strategic and corporate governance challenges confronting senior business leaders in Kenya, exploring their interrelationships and the adaptive strategies employed to navigate them. A qualitative, multi-case study design was employed, utilising in-depth, semi-structured interviews with 28 chief executive officers and board chairs from a stratified sample of listed and large private firms. Data were analysed using a thematic analysis framework. Analysis identified a core, cross-cutting theme of 'regulatory ambiguity', where frequent legislative changes and inconsistent enforcement created a pervasive environment of uncertainty. A significant proportion of participants (over 60%) explicitly linked this directly to strategic indecision and inhibited long-term investment. The findings illustrate that strategic decision-making is profoundly constrained not by isolated factors, but by a complex nexus of governance deficiencies and an unpredictable institutional environment, which collectively elevate operational risk and compromise strategic agility. Policymakers should prioritise regulatory stability and clarity in key economic sectors. Firms are advised to strengthen board risk oversight committees and develop more flexible, scenario-based strategic planning capabilities to enhance organisational resilience. strategic management, corporate governance, institutional environment, qualitative research, business leadership, Kenya This paper provides a novel, empirically-grounded framework linking macro-level institutional ambiguity to micro-level strategic stasis, offering a new lens for behavioural finance scholars analysing executive decision-making under uncertainty in emerging markets.