Policy can present any number of wicked problems for arts educators and advocates. The complexity of policy accompanied by a general lack of policy dexterity fuels the legitimacy gap between advocacy arguments and policy implementation and, thus, weakens the arts in the education policy realm. To help close the gap, common weak arguments in policy are identified by describing and illuminating various crypto-normative lines of inquiry that make for poor policy arguments. A method is then proposed for developing policy dexterity based on Jürgen Habermas' Universal Pragmatics. Starting from empirical foundations to establish, represent, and solve problems in education policy, a set of sensitivities are presented for advocates who are considering and communicating policy with other stakeholders. Those steps are finally applied to small and large-scale policy contexts. With the foundations and steps to more effectively argue specific political ideas instead of stopping at broad advocacy claims, arts advocates and teachers can hopefully work to close the legitimacy gap.