Chicagoland Chamber of Commerce > Events > Bridging the AI Gap: Intergenerational Communication, Skills, and the Future Workforce

Wednesday, June 24, 2026 9:00 am - 12:00 pm

Bridging the AI Gap: Intergenerational Communication, Skills, and the Future Workforce

Hosted by the Chicagoland Chamber’s Technology Council, Workforce & Talent Council, and Emerging Leaders Program

AI is accelerating workplace change—and how leaders experience and respond to that change often depends on when it entered their careers. As AI tools move from experiment to expectation, senior and emerging leaders are approaching adoption, communication, and skill-building from very different vantage points. Bridging the AI Gap creates a rare, structured dialogue between generations, inviting emerging leaders and senior executives to ask each other the questions that don’t often surface in traditional AI conversations.

Designed as an interactive, two-panel program, emerging leaders will share how they are using and adapting to AI today—then turn the tables by posing questions directly to senior leaders about decision-making, risk, adoption, and long-term workforce strategy. Senior leaders will do the same, challenging emerging professionals on readiness, expectations, and the skills that matter most in an AI-enabled workplace.

This program marks the first-ever joint collaboration between the Emerging Leaders Council, Technology Council, and Workforce & Talent Council—brought together because AI touches all three communities. The result is a candid, cross-generational conversation focused less on tools and hype, and more on trust, communication, capability-building, and the human skills needed to lead in the future of work.