Peter Merholz explores why UX/Design frequently struggles within modern organizations by introducing the concept of the legibility gap, which he adapts from James C. Scott's book Seeing Like a State. Corporations prioritize predictability and determinacy, valuing metrics like board feet or concrete software screens. Because much of design work is exploratory, qualitative, and indeterminate, it remains invisible or illegible to broader business operations. This fundamental disconnect causes designers to feel frustrated and underappreciated as companies demand standard software production rather than human-centered problem solving. Consequently, design leadership must act as a mediating lens, translating indeterminate creative practices for corporate stakeholders while expanding what traditional business operations recognize as valuable and legible work.