On the Leadership Language podcast, DEX Imaging CIO Patrick Adesso tells host Bill Tingle why creativity and taste now beat technical mastery.
©photo by tingleleadership.com
For most of the past three decades, the road to the top of a technology organization ran through the code. The best engineers became architects, the best architects became directors, and eventually one of them got the CIO seat. Technical mastery was the credential.
Patrick Adesso thinks that road is closing. He is also an unlikely person to say so.
Adesso is CIO of DEX Imaging, the largest independent office equipment dealer in the United States. He holds more than 10 U.S. and international patents, has built custom hardware, flies as a commercial pilot and still writes and ships code himself. Yet on the latest episode of the Leadership Language podcast, he told host Bill Tingle that the next great technology leader will not be an engineer.
“The next visionary, I don’t believe, is going to be an engineer,” Adesso said. “The coding of software has become commoditized by AI. I don’t think that’s an arguable point anymore.”
It is a striking claim from someone whose career was built on the very skill he now calls commoditized. Tingle, a former CIO who spent 35 years in enterprise technology and now coaches IT leaders on the human side of the job, built the conversation around an idea Adesso had first raised with him privately: the leaders who win next will be linguists, people who can see what should exist and describe it precisely.
What it looks like inside a company
Adesso’s view did not come from a conference stage. It came from watching his own organization.
At DEX, a Tampa-based company he puts at roughly 1,800 employees, hundreds of people had started using AI tools on their own before any formal program existed. Many IT leaders respond to that kind of shadow usage by locking it down. Adesso went the other way, turning the unofficial experimentation into a governed program and recruiting departments as partners.
The accounting team produced the moment that changed the conversation. After an audit, one staff member messaged him with a discovery.
“He said, we just finished an audit, and last year we paid $80,000 for some memos to be generated,” Adesso recalled. Using an AI assistant and the current year’s data, the employee had produced the memos himself. “He said, what are we paying for our membership? I said, you’re 100 bucks a month, buddy.”
The story traveled through the company and eventually reached the board. Adesso’s message to leadership was measured rather than evangelical. “We’re not an AI company,” he said. “But every decision we make around things like vendor selection, technology selection, process improvement, we should be considering AI as an alternative. I’m not saying it wins every time. But unless we do that, we will be behind the curve.”
From persuasion to prototypes
The shift has also changed how a technology leader wins an argument. Proposals to replace expensive legacy software once meant slide decks and months of persuasion. Adesso now arrives with something that already works.
“Now I come into that meeting with a prototype built, and they’re looking at this like, this feels done. When’d you do this? I said, well, I started Friday.”
The way he builds is its own departure. Rather than typing instructions at an AI system, he has it question him first, sometimes for hours.
“Instead of me firing commands at an AI, the AI is asking me questions about what I actually want to build,” he said. “I typically have a two to three hour dialogue with the AI before I ever start building anything.” Everyone he has taught the method found it uncomfortable at first, he said. Almost all of them kept using it.
That detail carries his larger argument. The hard part is no longer producing the code. It is knowing what should be built, and saying it clearly enough that a machine or a team can deliver it.
The producer, not the musician
Asked what the next generation of technology leadership looks like, Adesso reached for an analogy from music: Rick Rubin, the producer behind records by the Beastie Boys, Jay-Z and Adele.
“He is not really a musician,” Adesso said. “He is creative, and he can work with musicians and artists to draw out greatness. There’s going to be somebody that comes along who is innovative and creative and tasteful and can communicate. The Rick Rubin of agentic AI.”
The skills he expects to matter most over the next two years follow from that picture: creativity, taste, communication and a willingness to own the result. “You need to be able to talk to your team, talk to your sponsors, and you need to be able to be the person that accepts the outcome.”
Industry research points in a similar direction. Info-Tech Research Group’s IT Talent Trends 2026 report argues that AI will not replace IT workers, but it will push leaders to build the capabilities it cannot replicate, including critical thinking, adaptability and emotional intelligence.
For Tingle, whose coaching work focuses on IT directors and vice presidents preparing for the CIO role, that is the thread running through the show. In a recent episode, AdventHealth regional CIO Tony Qualls argued that technology organizations routinely promote strong engineers into leadership without preparing them for it. Adesso’s conversation picks up where that one left off, describing what the prepared leader will need to look like.
His advice to developers is to move toward people rather than away from them. “The developers that are going to survive, they’re going to complement their tool chest with AI development, and they’re going to focus on communicating with management, communicating with the business, QA, and design.”
It is, in other words, a language problem. Fitting, for a show called Leadership Language.
Listen to the full conversation with Patrick Adesso on the Leadership Language podcast.
Quotes have been lightly edited for length and clarity.
About the Leadership Language podcast
Leadership Language is hosted by former CIO Bill Tingle and features sitting and former technology executives talking about the human side of leading in IT: influence, communication, relationships and the decisions no one trains you for. Recent guests include Patrick Adesso, CIO of DEX Imaging, and Tony Qualls, regional CIO at AdventHealth. The show is available on Spotify, Apple Podcasts and YouTube. Technology executives interested in appearing as a guest can reach the show through tingleleadership.com.
About Bill Tingle
Bill Tingle is a former CIO, CIDO and CTO with 35 years in enterprise technology, including nearly two decades at Enterprise Mobility. An ICF Professional Certified Coach, he has coached more than 200 technology leaders and now works with IT directors and vice presidents preparing for the CIO role. More at tingleleadership.com.
About Patrick Adesso
Patrick Adesso is Chief Information Officer of DEX Imaging, the largest independent dealer of document imaging technology in the United States, headquartered in Tampa, Florida. He joined DEX in 2011, holds more than 10 U.S. and international patents, and is a commercial pilot with multi-engine and instrument ratings.
Disclaimer: This article is for informational purposes only. Statements and opinions attributed to Patrick Adesso, Bill Tingle, and other sources are presented as reported and have not been independently verified. The article does not constitute professional, business, or career advice.