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How do managers and staff react to strategic entrepreneurship? How can we minimize resulting job stress and maximize employee retention? We surveyed 1,975 managers and staff in 110 departments of a diversified healthcare organization on department-level entrepreneurial orientation (EO) (e.g., risk taking, proactiveness, and innovativeness), degree of role ambiguity in their job, and their strength of intention to quit. After validating manager and staff reports of EO, we estimated structural equation models for managers and staff. Our results demonstrate that strategic entrepreneurship can impact management and staff differently and thus requires a correspondingly customized design philosophy.