Leadership style has largely been studied through observable behavioral and performance outcomes, with limited attention to the underlying cognitive mechanism that shapes it. This study designed and explicated a model of smart leadership that links leadership style, through counterfactual thinking and fuzzy cognitive mapping, to a framework for explicating the cognitive structure underlying strategic decision-making. An exploratory mixed-methods design, situated within a pragmatist paradigm, was used; the population comprised all 32 senior managers of the Iranian Offshore Oil Company (a full census of the target population), and data were collected through eight content-validated, scenario-based questionnaires. Managers' open-ended responses were coded by two independent coders (inter-coder reliability: Cohen's kappa = 0.81) according to the direction and agent of counterfactual thinking, represented as fuzzy cognitive maps, and analyzed using graph-theoretic indices. Descriptive analysis revealed distinct patterns linking leadership style, counterfactual-thinking pattern, and cognitive network structure; dominant leadership-style patterns at the scenario level showed descriptively distinct patterns in the density and complexity of the resulting cognitive networks, and combining leadership style with counterfactual-thinking pattern yielded an exploratory typology of distinct cognitive patterns among managers. The findings support the conceptual distinction of smart leadership from digital, contingency-based, cognitive, and AI-based leadership, offering a conceptual foundation for developing and validating a context-specific tool to support the evaluation, development, and succession planning of managers of the Iranian Offshore Oil Company; extending it to other high-risk industries requires independent empirical testing. The main contribution of this study is an integration of localized counterfactual scenario-writing with fuzzy cognitive mapping to quantitatively represent leaders' cognitive structure.