DPIT: IT's Pushback Problem w/ Dr. Charles Harris Jr. (1:05) #366
Dissectiing Popular IT, Monday, August 4th, 2025
Why do IT leaders face more pushback than any other department?
Dr Charles Harris, Transformational CIO at Tampa Bay Buccaneers, knows this pain firsthand.
Running IT for a Super Bowl-winning organization taught him that the biggest technology challenges aren't technical-they're cultural.
Harris breaks down why IT leaders stay trapped in the loneliest seat in business, constantly fighting to prove their value to executives who fundamentally don't understand the decisions being made.
From dealing with CEOs who spend six figures on consultants to validate what you said months ago, to managing the exhausting cycle of explaining complex technology choices to non-technical leadership, Harris reveals the communication strategies that finally broke through.
He shares his 'Gardener Methodology' for making IT the center where all organizational decisions flow, and explains why being selfish with executive communication isn't selfish-it's strategic.