This study demonstrates how knowing the digital literacy of those they serve helps information communications technology (ICT) leaders adjust their perspective-taking. Using a pre-and post-survey design assessing ICT leaders on changes in their thinking around key responsibility areas: support during new software adoption, troubleshooting an issue and preparing for a system upgrade. The study used a self and other-rated paired survey model using Computer Attitude Scale and Computer Self-Efficacy instruments to measure ICT leaders and those they serve. 31 ICT leaders at a west coast university participated in this study, and 85 non-ICT workers whom the ICT leaders serve. 31 ICT leaders at a west coast university participated in this study, along with 85 non-ICT workers who the ICT leaders serve. This study indicates that ICT leaders did indeed view the laypeople's digital literacy differently than the laypeople did. And that by showing ICT leaders the differences, they adjusted their support expectations according to the laypeople's self-ratings.