6 Questions Every Business Leader Should Ask Before Deploying AI

Most companies betting on artificial intelligence are not losing because of their technology. They are losing because they have not changed how they work. That is the core finding from George Westerman, a senior lecturer at MIT Sloan School of Management, who presented at the MIT Enterprise AI Forum in May 2026.

Westerman has studied digital transformation with organizations including Takeda Pharmaceuticals, global infrastructure firm Ferrovial, and Dentsu Creative. His research identified six questions that determine whether an AI initiative will scale or stall.

The Six Questions

• What is your shared ambition? Leaders at Rio Tinto framed AI initiatives around safety rather than efficiency, telling employees: "We want to build a mine where no miner will ever get hurt again." Without a compelling shared purpose, even well-funded AI efforts lose momentum.
• How will you govern your efforts? HCA Healthcare uses a steering committee that evaluates every AI use case for risk, business value, and feasibility before development begins, then checks in again before piloting and before scaling. Governance functions as a steering wheel, not a set of brakes.
• How will you capture value by scaling AI efforts? Studies consistently show 70 to 95% of AI pilots fail to scale across the enterprise. Westerman advises leaders to plan for organization-wide rollout from day one and to actively maintain executive support throughout.
• Is your tech foundation solid? Every organization Westerman has worked with has needed data cleanup before deploying AI. The right approach is incremental, not all-at-once.
• Is your culture ready to move fast? DBS Bank engaged its entire workforce in digital and AI learning. HCA Healthcare redesigned nurse shift handoffs with AI assistance, cutting a 50-minute process to under 25 minutes by involving nurses throughout.
• Do your people have the right skills to work with AI? Proactive communication about how roles will change is essential. Organizations that tell employees what is coming and how they will be supported see better adoption outcomes.

Read the full article on MIT Sloan Management Review