CIOs Need To Walk Around The Plane Before Switching On AI Autopilot

The AI rush has the shape of every rush before it. The web in 1995, then e-commerce, then the dot-com correction that followed. The numbers back the déjà vu: operationalizing AI now tops the CIO priority list even as adoption stalls and gains plateau. What keeps getting skipped this time is any inspection of whether the business can support the ambition.

Jason Cohen is the founder and CEO of Right Stack Advisors, which advises private equity firms, their portfolio companies, and growth-stage businesses on the gap between strategy and execution. He was most recently CTO of Clarest Health and spent more than 25 years at Omnicom Group, serving as CIO of the DAS Group of Companies and CEO of Consolidated Data Services, its shared-services arm. The AI rush, in his telling, runs on FOMO.

"FOMO affects everybody. When somebody says you could use AI to reduce your cost, to speed up your business, to grow your business, who's not listening?" Cohen said. "They're misinterpreting vision and ideation for work." He sees two failure modes come up again and again.

• Nobody asks why: "I don't think the right questions are being asked. Why do I need AI? What are the problems I'm trying to solve?" he said. Data quality, expertise, and a financial case that holds up are the real blockers to adoption, but they rarely make the pitch deck.

• The SMB squeeze: He aims the sharpest warning at smaller companies, where AI is spreading fast and breaking in new ways. "They're going to spend $100,000 with a big consulting firm, basically to be told you need to do X, Y, and Z, and then it's going to be a million," Cohen said. "Small to mid-sized businesses are getting squeezed out of AI and the technology boom because nobody wants to spend the time." His prescription: work the early maturity levels first and conduct exploration through departmental use before treating AI as a competitive advantage.

His fix borrows from an aircraft's cockpit. Before takeoff, a co-pilot circles the aircraft looking for cracks, worn tires, and anything that could ground the flight. "I would do that walk around my company," Cohen said. "What is the state of our infrastructure? What is the state of our security? What is the state of our governance and audit? What are the pieces we need to fly this plane or run this business?" When the plane takes off, he explained, the computer basically runs the show. "But that computer couldn't run the show if there was a crack in the wing or a nail in the tire."

The inspection is step one. The harder demand is measurement.

• Outcomes or nothing: "Any AI initiative is not going to be measured on whether the model works," Cohen notes. "It's going to be measured on whether it delivers meaningful outcomes." His scorecard puts a KPI, target, and an owner on every row: revenue growth under the CEO and sales, productivity under the COO at five to 15 hours saved per employee each month, cost reduction under the CFO at 10 to 20 percent in operational savings. Weigh it, then hold the names on it accountable. "Ownership and accountability are what's really lacking."

• Every seat, one lens: The table settles the fight over who owns AI by splitting the lenses. The CEO takes growth and strategy, the COO workflow and scalability, the CFO ROI and budget, the CIO and CTO readiness and integration, the CISO risk and data protection, sales and marketing the pipeline. HR gets a seat too. "Trust me when I tell you, recruiting is going to come into play," he said.

The obstacle left standing is one that Cohen admits to having helped build. Around 2011, leaders carved technology into infrastructure, security, and help desk, each split defensible on its own, and the divisions hardened into the culture AI now compounds. Developers want stacks running in five minutes, governance wants process, the help desk wants no part of either, and the leadership job is shifting to referee it all. For a forthcoming white paper, he interviewed six or seven companies, and every group named the same problem. "We as leaders have created this beast," Cohen said.

In Cohen's view, the assignment of addressing it goes to the CEO. "We need to bring those groups together. For collaboration, for accountability, for reduction of finger-pointing," he said. "And we need to identify someone who owns that and holds it accountable."