AI is becoming increasingly capable of making decisions and taking action. But as organizations move toward greater autonomy, who is responsible for ensuring those decisions reflect the right information, business priorities, and human values?

That question set the stage for CDO Magazine’s Chicago Executive Boardroom Dinner discussion on October 28 at Morton’s The Steakhouse.

Executives representing healthcare, financial services, technology, insurance, and other industries reconnected with peers and exchanged perspectives on the growing role of AI in business and everyday life.

The event also offered an opportunity to compare experiences with data readiness, governance, and the challenges of moving autonomous AI from promising applications into trusted business operations.

Beyond Automation: The Challenge of Autonomous Judgment

For organizations introducing AI agents, building the technology is only part of the challenge.

The Chicago executives considered what changes when AI moves beyond automating individual tasks and begins making decisions that affect business operations.

Among the questions raised was how organizations determine whether their data is ready to support autonomous systems. Traditional measures such as accuracy, completeness, and freshness remain important, but they don’t necessarily establish whether an AI agent has the information and context needed to make a sound decision.

Molly King, Senior Manager, AI Solutions at Blue Cross and Blue Shield of Illinois, Montana, New Mexico, Oklahoma & Texas, captured the shift:

“Building isn’t the bottleneck anymore. What’s new is moving from automating tasks to productionalizing autonomous judgement at scale. Doing that in a way organizations can trust is a leadership challenge as much as it is a technical one.”

Her observation connects two challenges facing organizations: making AI systems capable of acting independently and establishing the confidence to let them do so.

The executives also considered how data teams and AI teams can align their expectations when defining readiness, particularly when technically accurate information may not provide the context needed for reliable decisions.

When Trust Becomes a Leadership Decision

Another question for Chicago’s executives was how organizations can balance the opportunities of autonomous AI with the responsibility of overseeing its decisions.

As businesses explore agentic AI, they must consider not only what their systems can accomplish but also whether they can stand behind the decisions those systems make.

The exchange raised questions about data relevance, changing business conditions, and the potential consequences of AI learning patterns from information that organizations may later wish they had handled differently.

These considerations make AI governance an increasingly important part of enterprise AI adoption.

For leaders responsible for deploying these technologies, the challenge is to establish appropriate safeguards while still enabling innovation.

The Human Side of an AI-Driven Future

While enterprise AI provided the foundation for the evening, the reflections extended beyond technology and business operations.

For Patrick Chew, Burtch Works Chief Data and AI Officer, the conversation offered an opportunity to consider how AI is influencing decisions, relationships, and everyday life.

Chew reflected:

“Another wonderful evening reconnecting with our CDO Magazine cohorts, exchanging perspectives, sharing experiences, and continuing to explore our collective journeys in Data and AI.”

He continued:

“One thing has become increasingly clear – AI is no longer a conversation about the future. It is already part of our present. Its influence is moving well beyond the workplace and technology landscape, finding its way into how we make decisions, communicate, learn, raise our families, build relationships, and navigate everyday life.”

His reflection also pointed out about the responsibility leaders have in shaping how AI is adopted:

“But perhaps the bigger question is no longer simply how AI will change the way we work and live.

It is whether we are consciously shaping that change, or simply allowing ourselves to be shaped by it.”

Chew concluded with a perspective that extends beyond technical capabilities:

“In other words, the future of AI is not just about what machines become capable of doing, but what we, as humans, choose to become in response.”

Continuing Chicago’s Executive Connections

The Chicago gathering also provided an opportunity for executives to reconnect with familiar peers, meet leaders from other industries, and exchange experiences with the opportunities and challenges of enterprise AI.

Data, AI and Technology Leaders Who Joined the Chicago Conversation:

• Allyson Alston*, Former Mars Veterinary Health Global Vice President, Data & Analytics
• Kalyani Boddupalli, Former Double Good Vice President, Business Applications, Data and Analytics
• Dan Cromer, Former Walker & Dunlop Senior Vice President of Product, Data – WDTech
• Patrick Chew*, Burtch Works Chief Data and AI Officer
• Molly King, Blue Cross and Blue Shield of Illinois, Montana, New Mexico, Oklahoma & Texas Senior Manager, AI Solutions
• Shuen Mei, Harbor Capital Advisors Vice President, Director of Software and Data Engineering
• Gokula Mishra*, Former Direct Supply Vice President, Data Science
• Prasannal Nithyanandam*, Elevance Health Head of Responsible AI/AI Enablement
• Enrique Quevedo, UChicago Medicine Senior Director, Strategy & Analytics
• Tim Riddle, Premier Inc. Senior Director / Executive Leader – Applied AI, Innovation & Strategic Partnerships
• Brad Rosenberg, Hightower Advisors Manager of Enterprise Data Governance and Stewardship
• Kader Sakkaria, Marsh Global Head of Data Strategy
• Frank Sung, Loop Capital Markets Vice President, Data Management
• Anurag Voleti, Xsolis Vice President, Data Science
• George Wang, FinTank Chief Information Officer
• Christopher Koch, Salesforce Healthcare Territory Account Manager
• Chris Pierpan, Salesforce Global Leader, Communities of Practice
• Angela Losacco, Salesforce Regional Vice President, Solution Sales
• Anthony Losanno, CDO Magazine Managing Director

*Allyson Alston, Patrick Chew, Gokula Mishra, and Prasannal Nithyanandam are CDO Magazine Global Board members. 

CDO Magazine thanks Informatica and Mulesoft from Salesforce for supporting the Chicago Executive Boardroom Dinner and helping create an opportunity for regional data, AI, and technology leaders to connect and exchange experiences.