Microsoft rolled out its Copilot AI assistant to its own sales force the way it had introduced other new tools. Employees experimented with the technology, then stopped using it. "They didn't see it as useful in the flow of their work," Katy George, corporate vice president, AI and work transformation at Microsoft, said during Newsweek's October 21 webinar, "Overcoming Barriers to AI Transformation in Legacy Industries." The company responded by sending engineers to shadow sales representatives and understand how they actually did their jobs.
The collaboration led to more specialized tools, including Sales Chat, a set of prompts built on Copilot that helps account executives prepare for meetings, and agents that simplify processes and provide coaching. The engineers worked directly with "the people doing the work, the ones who have the tacit knowledge of what's important," George said. Joining George on the panel were Matt Sanchez, president and chief operating officer at Yahoo; Durga Malladi, executive vice president and general manager of technology planning, edge solutions and data center at Qualcomm; and Rodrigo Madanes, global next frontier technology and AI officer at EY.
Gabriel Snyder, Newsweek's executive editor, enterprise, moderated the webinar, which was presented by Cognizant. At Yahoo, Sanchez encountered a different obstacle. Teams were experimenting with AI on side projects, but the company's existing development tools and systems weren't ready for agents to work on its core software.
"It became a kind of go-slow-to-go-fast moment for the company," Sanchez said. Yahoo ran pilots to test whether spending four to six weeks retooling its code and development tools would allow engineers to move faster afterward. The results persuaded business leaders to expand the effort across the company, one engineering team at a time.
Such preparation can extend beyond software, Malladi said. "There's a lot of groundwork that needs to be done before you can start just throwing AI at every single problem out there," he said. At the beginning of the session, Snyder cited research published by Cognizant illustrating how many companies have struggled to translate their AI investments into measurable improvements.
In a survey of 1,200 senior business leaders, only 32 percent reported tangible gains in business productivity, while about one-quarter said their organizations had paused or discontinued AI deployments. The study also found that investment priorities mattered. Among companies with less mature technology infrastructure, those pursuing broader, nontechnical AI investments were 60 percent more likely to pause or abandon a deployment than those concentrating on technical foundations such as computing capacity and data readiness.
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