9 Mistakes Leaders Make With AI Strategy

At the 2025 MIT Sloan CIO Symposium, many tech and business leaders voiced the same frustrations — about AI initiatives that aren’t delivering business value, pilot projects that never made it to production, and their ongoing struggle to figure out what’s going wrong.

So we asked those leaders and AI experts in the room to share lessons learned by asking a key question: What’s a common mistake you see organizations still making when shaping AI strategy?

Their answers revealed a pattern. “The low-hanging fruit — it’s not really as low as we think it is,” said MIT Sloan senior lecturer George Westerman, warning about overestimating AI’s capabilities. But the challenges go much deeper than technical limitations.

Monica Caldas, executive vice president and CIO at Liberty Mutual Insurance, stressed the need for cross-functional teams and cultural change management, and to rethink how organizations operate.

McKinsey partner Hannah Mayer made a telling observation about speed of change: “Employees are three times more willing and excited to leverage AI in the workplace than their leaders expect.” She pointed to executive disagreement as a bottleneck that’s holding organizations back.

Watch the video to hear advice about avoiding these critical mistakes:

• Setting unrealistic expectations by overestimating current AI tool capabilities.
• Missing the transformation opportunity by treating AI like just another software tool.
• Getting stuck in pilot mode and coming up short on production deployments.
• Encountering executive hesitation and moving forward too slowly.
• Forgetting the human factor and focusing too much on technology rather than people.
• Underestimating the security risks and failing to build resilience.

These AI strategy errors are avoidable once you know what to look for. Watch this video to learn from your peers’ experiences and avoid the pitfalls that are costing organizations time, money, and competitive advantage.

Video Credits

Laurianne McLaughlin is senior editor, digital, at MIT Sloan Management Review.

M. Shawn Read is the multimedia editor at MIT Sloan Management Review.