In an effort to integrate security and privacy-focused thought processes throughout everything we do, we introduced a focused "Executive Cybersecurity Tabletop Exercise" format in our Data Protection Officer training sessions this year, which were also presented to district superintendents. We have found these sessions a great way to fast-track collaborative problem-solving sessions around cybersecurity with experienced IT and leadership professionals. In this session we will talk about the need for executive tabletop exercises, the protocol for conducting the exercise, and walk the audience through a sample tabletop cybersecurity exercise.