Executives were caught off guard by the rapid rise of AI and the skills needed to turn aspirations into reality. But their leadership is essential to the success of AI initiatives.
As adoption efforts expand, enterprise leaders are upping their AI know-how, according to a General Assembly report published Tuesday. Owned by Adecco Group, the provider of technology boot camps surveyed 650-plus company leaders, including VPs and directors.
More than 3 in 5 leaders have attended AI training this year, up from 43% in 2024. A majority of leaders are also encouraging their teams to use AI, jumping to 73% in 2025 from 55% last year.
Upskilling efforts are helping build confidence among enterprise leaders, according to the company. Three-quarters of respondents believe they have the knowledge to make AI vendor decisions for their department this year, a bump up from 61% in 2024. Nearly 3 in 5 are “very” or “extremely” confident that they know how to use AI tools without compromising proprietary data. Last year, less than half said the same.
Over the past few years, enterprises have struggled to turn AI hopes into reality. Project failures are up, roadblocks remain and skill gaps persist throughout the business. The pressure is on leaders to work out the kinks and produce desired results.
“If you’re questioning why you aren’t seeing ROI from AI investments, look at the top, and make sure leadership is equipped with the technical and change management skills that move the needle," Daniele Grassi, CEO of General Assembly, said in a release accompanying the report.
The pace of change can weigh on technology leaders. More than half of senior executives entered 2025 feeling like they were failing amid AI’s rapid growth, according to EY research published in December.
Upskilling for everyone
Training has become an essential part of enterprise AI plans. Walmart, S&P Global and American Honda — among other businesses — have invested time and resources into creating curricula that enable their workforces to use the technology safely and effectively.
As part of Clearview Federal Credit Union’s AI efforts, the company sees upskilling opportunities as a way to level up implementation plans and sharpen execution, according to CIO Raymond George.
“We contracted with a company to do a bootcamp for our executive team and potentially our board,” George told CIO Dive. “We’re trying to put in a training so that everybody has face-level understanding in the company about AI.”
Leaders from Ulta, Lowe’s and Principal Financial Group have emphasized the importance of upskilling opportunities this year to bring leaders and employees along for the journey.
“I have to go through training … because things keep changing in my field,” Chandhu Nair, SVP of AI, data and innovation at Lowe’s, told CIO Dive during the summer.
Technology chiefs benefit just as much as rank-and-file staffers from avenues to sharpen their skills.
“I have to think about how to adapt,” Nair said. “The next five to 10 years is going to be a constant learning, unlearning [and] relearning experience.”
