A stark divide often exists between a policy’s goals and its implementation. This policy “implementation gap,” signals a failure to take into consideration the complexity of a system or issue. Failure often results in policy that is a misfit for the issue of concern and is lacking in the hoped for remedial or preventative impacts. This study explores policy prototyping as a remedy for policy failures in bills aimed at privacy protection. After selecting three privacy-related bills, we created prototypes that represented one of many ways that privacy policy could be translated into features in online platforms. Using the prototypes, we conducted 41 semi-structured interviews to gather feedback and insights on the challenges with the laws. Our findings illustrate how different roles emphasize protections, harms, and word choice when communicating levers of change like civil rights protections in law to privacy design elements. This solidified the opportunities to better bridge policy and practice by outlining common and distinct bill themes.