Why Chicago organizations are asking hard questions about AI and judgement
Chicago's trading floors and risk desks have used algorithmic decision-making longer than most industries. That history makes the current moment sharper here, not softer. The question is no longer whether AI can process information faster than a person. It is whether the people working alongside AI still know how to think when the model is wrong.
Insurance firms on Wacker Drive and consulting practices across the Loop are deploying AI tools that shape recommendations, flag risk, and summarise client information. That is useful. It also creates professionals who are increasingly good at reviewing outputs and increasingly out of practice at forming independent views.
Chicago's regulators and clients are starting to notice. When something goes wrong, the question asked is not 'what did the model say?' It is 'what did you decide, and why?' That is the gap Steve's talk addresses directly.
What Steve covers when he speaks in Chicago
Steve's talk draws on his book 'Cognitive Sovereignty' to give audiences a concrete framework for staying sharp as AI takes on more cognitive work. He covers how overreliance on AI recommendations erodes the skills that got people into senior roles, and what to do about it practically, not philosophically.
For financial services and professional services audiences, he focusses on the specific moments where deference to AI is highest and the cost of weak judgement is greatest: client advice, risk assessment, and high-pressure decisions under time constraints.
Attendees leave with a clear way of thinking about when to follow the model, when to push back, and how to build organizations where people still own their conclusions.
Topics for Chicago audiences
Steve speaks on cognitive sovereignty, the judgment economy, AI and creativity, and related topics. Full details on the Speaking page.
Book Steve for your Chicago event
If you are planning a corporate conference, leadership event, or offsite in Chicago and want to discuss whether Steve's work is a good fit, the Work with Me page has the details.