This article is part of our series on AI and executive leadership, based on Riviera Partners’ Future of Tech Leadership 2025 report. The first, “Why AI Ambitions Are Outpacing Reality at an Alarming Rate,” explored the brewing readiness crisis. The second, “Revealed: How AI Is Rewriting the Tech Org Chart,” looked at the rise of new executive roles. The third, “What High-Readiness Companies Do That Others Don’t,” showed how the best are pulling ahead. This article examines where most companies stumble at the start—the early organizational gaps that derail AI readiness.
3 Takeaways
- The first cracks in AI readiness appear in execution discipline, ownership, and fluency.
- Companies often “bolt on” AI responsibilities instead of redesigning accountability.
- Unless early gaps are addressed, ambition will always outpace reality.
When it comes to AI, most companies start with big promises and big investments. But according to Riviera Partners’ Future of Tech Leadership 2025 report, the real challenges begin long before AI is scaled across the enterprise.
The survey of more than 1,000 technology executives shows that the first gaps emerge in execution discipline, accountability, and leadership fluency. These early cracks explain why as few as 2% of companies qualify as structurally “high readiness”
Strategy Without Execution
As noted in our opening article on the AI readiness crisis, nearly two-thirds of leaders (62%) call AI “very important” to their enterprise strategy. Yet only 58% believe they have the leadership to deliver.
The shortfall isn’t about enthusiasm—it’s about organizational muscle. Forty-two percent of executives say their teams lack change management or execution discipline, while 35% cite limited AI fluency and strategic agility as barriers. Without these fundamentals, strategy becomes little more than a slide deck.
Ownership Without Accountability
The second gap shows up in role design. As we explored in “How AI Is Rewriting the Tech Org Chart,” most organizations are expanding existing roles—usually CTOs or product leaders—to absorb AI responsibilities. Just 39% have created a new, AI-specific executive role.
This bolt-on approach creates blurred lines of accountability. Who really owns AI? Who reports progress to the board? When no one is formally responsible, execution falters.
By contrast, high-readiness organizations—profiled in “What High-Readiness Companies Do That Others Don’t”—move early to create Chief AI Officers, centralize hiring, and embed accountability into the board pipeline.
Fluency Without Depth
The third gap lies in leadership fluency. Many executives are conversant in AI but not fluent enough to lead structural transformation. Thirty-five percent of respondents cited AI fluency as a top barrier to readiness
This lack of depth matters. Without fluency, leaders may invest in tools but fail to align them with workflows, talent strategies, or long-term governance. In effect, companies risk becoming AI “curious” but not AI-ready.
Why Gaps Compound
What makes these early gaps so dangerous is how quickly they compound. Strategy without execution leads to failed pilots. Ownership without accountability leaves initiatives stranded. Fluency without depth limits scale.
The result is a cycle: ambition gets louder, investment grows, but progress stalls. That’s why readiness isn’t just about having the right tools or vision—it’s about redesigning early, with structure and accountability baked in.
Closing the Gap
The Future of Tech Leadership 2025 report makes clear that the companies closing these gaps are the ones building durable advantage. They are treating AI as an organizational design challenge, not just a technology trend.
Explore the Full Report and Benchmark Your Readiness
The Future of Tech Leadership 2025 report offers data from more than 1,000 senior executives on readiness, org design, and hiring trends.
Readers can also take the AI Organizational Readiness Quiz to assess their own structures, compare to peers, and get tailored recommendations
👉 Download the full report and take the readiness quiz to see how early gaps could impact your readiness journey.
About Riviera Partners
Riviera Partners is a global executive search firm specializing in technology, product, and design leadership. With over two decades of experience and a proprietary platform that combines deep recruiting expertise with data-driven insights, Riviera is the go-to talent partner for venture capital, private equity, and public companies. Learn more at www.rivierapartners.com.