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Chicago Exchange 2026: Leading the AI Era — From Insight to Action

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Thu est. 9 hours
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What We’ll Explore Together Leading the AI Era — From Insight to Action

A live in-person exchange where senior talent and business leaders work through real-world challenges, reshaping leadership, culture, and execution in the AI era.

Lead the AI Era—From Insight to Action

In 2026, the mandate for HR and L&D has shifted from diagnosing organizational symptoms to designing intentional talent experiences. It is no longer just about what individuals learn; it is about how teams build capability together in the flow of real work.

Chicago Exchange 2026 is a live in-person exchange for senior talent and business leaders working through the leadership challenges that will define the AI era.

Three-step ELE model showing Real Business Problems leading to Peer-Powered Decisions and Implementation.

How the Exchange Works
  • Real-World Challenges: We start with the problems leaders are actually trying to solve — not abstract trends or polished case studies.
  • Design Charrettes: Small groups work the challenge together, pressure-test assumptions, and shape sharper choices.
  • AI Practical Labs: The strongest ideas move into practical action planning — where AI becomes a tool for execution, not another shiny object.

From Challenge to Action

ELE is leaning into a simple workflow: real-world challenges → peer-powered decisions → implementation.

At Chicago Exchange 2026, leaders will bring the issues showing up in the work: culture drag, capability gaps, adoption friction, leadership readiness, and the execution risks that come with AI-era change.

You won’t just hear about transformation. You’ll work through it with peers — and leave with clearer decisions, smarter next steps, and practical ways to move the work forward.

Watch: How ELE turns real-world challenges into peer-powered decisions and practical next steps.

What to Expect

  • Real executive dialogue: Practical, unscripted exchange with senior leaders working through AI-era leadership challenges.
  • Design Charrette work: Small-group collaboration around real problems, sharper choices, and practical next steps.
  • AI Practical Lab mindset: Explore where AI can reduce friction, improve handoffs, and support execution — without pretending the tool solves the leadership work.
  • Peer-powered momentum: Leave with clearer thinking, useful connections, and ideas you can bring back to the business.

Real-World Challenges We’ll Work Through

The agenda will be shaped around the leadership and workforce challenges showing up across the ELE community, including:

  • Building leadership readiness for AI-era change
  • Reducing adoption friction across teams and functions
  • Strengthening culture when work is shifting fast
  • Turning AI interest into practical workflow improvement
  • Helping managers lead through ambiguity, speed, and execution drag

Who Should Be in the Room

This exchange is designed for senior leaders responsible for leadership, talent, culture, workforce transformation, and execution.

  • CHROs and senior HR executives
  • Chief Learning Officers and heads of talent
  • Leaders responsible for leadership development, organizational effectiveness, and employee experience
  • Business leaders working through AI-era change with their teams

Hosted at CNA Insurance

Chicago Exchange 2026 will take place at CNA Insurance’s downtown Chicago office at 151 North Franklin.

CNA gives this exchange the right setting: a modern business environment in the heart of the Loop, built for practical conversation, cross-company perspective, and the kind of working dialogue leaders need as AI reshapes work, culture, and execution.


Register Now

Ready to work through the leadership challenges shaping the AI era?

Join senior leaders at CNA Insurance for a live in-person exchange built around the problems leaders are actually trying to solve — with peer-powered decisions and practical next steps.

Why Attend?

  • Bring sharper questions: Work from real business and workforce challenges, not generic trend talk.
  • Learn with peers: Compare how other leaders are handling AI-era change, culture drag, adoption friction, and execution risk.
  • Leave with momentum: Walk away with clearer decisions, practical next steps, and useful peer connections.

Help Shape the Agenda

Chicago Exchange 2026 will be built around the real-world leadership and workforce challenges showing up across our community.

Have a challenge your team is working through? Share it with ELE so we can shape the exchange around the situations leaders are actually facing — not theory, not trend-chasing, real work that needs better answers.

Submit a challenge:
https://www.ele.llc/faqs/share-top-of-mind-challenges 

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