We develop a theory of opinionated bosses -- this is where a boss reveals her opinions to a worker who is tasked with gathering information. When the worker gathers information across multiple tasks, which he views as substitutes, selectively revealing opinions to the worker on one task redirects his effort across tasks. The cost is that the worker becomes a yes man. We show that i) being opinionated can go hand in hand with weaker opinions, ii) the organization can have inefficiently high levels of conformity and initiative co-existing side by side, and that iii) opinions improve the tradeoff between insurance and incentives when the worker is risk averse