Every leader hopes to see the hard work of their peers and team members rewarded with positive results and measurable success after a large, organization-wide initiative. For projects as impactful as a new software deployment, there must be a concerted effort to plan and think strategically. Oftentimes, however, the critical planning stage of the deployment does not allow for meaningful discussions to take place. Executive leadership may approach a software deployment with a high-level vision for optimal outcomes, but not communicate these expectations clearly enough for them to be examined properly before project work begins.