In this interview, we discuss the two roles of a technology leader: To manage technology and to help differentiate their enterprises. We also discuss some of the education programs CISR has for management teams to increase digital savviness, and some of the long-term implications the pandemic will have on the world. We also discuss the results and implications from several of the machine learning based studies done by CISR that show that less than half of CIOs or CTOs and less than a quarter of boards are digitally savvy. Lastly, we discuss his view on boards, including the importance of having at least three digital savvy directors on a board, the three major aspects of a board, and the value of having CIOs on boards, among a variety of other topics.