After leaders at Johnson County Public Schools (NC) developed a new strategic plan, JOCO 2020, they worked hard to ensure that their new plan would be implemented with fidelity and commitment from each stakeholder. Change can bring anxiety as well as exciting opportunities to a district. Before implementation, several big decisions needed to be made. One such decision was the need to reassess insurance benefits. Previously, emotion‐laden, big‐money decisions of this nature had not utilized a formal, transparent, and systematic evaluation process. Consequently, there was a lack of confidence and trust in decisions that had been made. Read how they used process in this decision and more to take the plan from the aspirational to the operational.