When academic researchers, business commentators, and boards of directors have debated the merits of hiring new CEOs from outside the firm, the implicit or explicit assumption typically made is that outsider CEOs will provide an advantage in achieving strategic change. In this study, we challenge this assumption by employing a duality perspective on stability/change, and we provide an original conceptual framework to posit that it is the presence of corporate stability (ordinary succession, a long‐tenured predecessor CEO, and good firm performance) that allows outsider CEOs to generate a greater degree of post‐succession strategic change. We use extensive longitudinal data from U.S. airline and chemical industries between 1972 and 2010 to test our hypotheses, and we discuss how our supportive findings challenge long‐standing assumptions regarding the outsider succession‐strategic change relationship, and we advocate embracing the non‐intiutive notion that stable (unstable) conditions can be enablers (barriers) of strategic change for outsider CEOs.