AbstractGeneralist chief executive officers (CEOs) have accumulated transferrable general skills by working in multiple firms or industries. Recent decades have witnessed an increasing demand for generalist CEOs, which has resulted in a favorable job market for them. Favorable outside job opportunities reduce generalist CEOs’ career concerns and increase their agency problems and risk‐taking incentives. We examine the relation between generalist CEOs and conditional conservatism. On the one hand, conditional conservatism could be positively associated with generalist CEOs because debtholders and shareholders often demand conservatism to alleviate heightened agency problems. On the other hand, a negative association could obtain because generalist CEOs can (1) create better information environments for firms, reduce information asymmetry and lessen stakeholders’ demand for conservatism and (2) have greater bargaining power and reduce the supply of conservatism. We document a positive association between generalist CEOs and conditional conservatism and show that the relationship is more pronounced in firms with a higher demand for conservatism. Our results are robust to a variety of sensitivity tests.