Abstract: Leaders increasingly face complex, ambiguous decisions in volatile environments where traditional advisory networks may prove insufficient. This article examines an emerging practice: constructing virtual personal boards of directors using generative artificial intelligence to simulate diverse advisory perspectives. Drawing on leadership development literature, decision-making theory, and early practitioner accounts, we explore how AI-enabled persona modeling complements human advisory relationships. The framework presented integrates evidence on personal boards, cognitive diversity, and AI augmentation, while offering structured guidance for executives seeking to expand their strategic thinking capacity. Organizational examples span technology, consumer goods, and professional services sectors. We conclude that hybrid advisory systems—blending human trust with AI-enabled cognitive range—represent a promising frontier in executive development, provided leaders maintain critical discernment and ethical grounding.

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