Our objective in this paper is to illustrate and better understand the unavoidable arbitrage between incentives and flexibility in contexts of asymmetric information and to characterize the general features of an appropriate response to this challenge. We show that procedures and institutions in organizations which reduce the capacity to implement change may be necessary to generate the optimal level of inertia. We show that more flexibility in adapting to changing conditions or new information, typically known or observed by either the agent or the principal but not both, may come at the expense of efforts exerted up front by the agent to make the organization more successful. There is a trade-off in this context between ex ante efforts and ex post flexibility of adaptation.