How a session in Chicago is put together
Every keynote is tailored after a briefing call, and the larger engagements start before the day rather than on it: a diagnostic of the client's own people, so the room hears its own evidence rather than somebody else's. What the room leaves with is written down.
What that has looked like: an agency business convening Asia, Asia-Pacific, EMEA and North America into one event, where the work was naming the recurring situations nobody had vocabulary for, and the company took that wording into its strategy; and a division of a very large company permitted exactly one AI tool, which after the constraint was examined moved to a multi-tool sandbox with different functions choosing different models, then repeated across further divisions.
Six of the seven engagements published on this site produced further work after the session rather than at it. The seven are set out in full at case studies, each with a line saying what it does not show.
How to read these examples. They are published to show how the work is put together, not as a client list for Chicago. Most engagements are covered by confidentiality and are described without naming anyone; where a client is named anywhere on this site, it is with their agreement.
A duty in force, and no rules to follow
Public Act 103-0804 added subsection (L) to the Illinois Human Rights Act, in force since 1 January 2026. It makes it a civil rights violation for an employer to use artificial intelligence in recruitment, hiring, promotion, discharge, discipline or the terms of employment in a way that discriminates on a protected basis, or to use zip codes as a proxy for protected classes. It also requires notice to an employee that AI is being used for those purposes.
The statute then directs the Illinois Department of Human Rights to adopt the rules needed to implement and enforce it. Eight months on, those rules do not exist. The administrative code contains no reference to artificial intelligence, and the department’s own employer compliance material does not mention it.
So Illinois employers carry a live obligation whose operative detail has not been written. That is a more honest description of where most organisations actually are than any compliance framework offers, and it is why the useful session here is about judgement rather than about rules. One textual detail worth getting right on stage: the notice duty is owed to an employee, and the statute does not say applicant.
Illinois was first at this, and has been for six years
The Artificial Intelligence Video Interview Act has been in force since 1 January 2020, the first statute of its kind in the United States. It requires consent and explanation before AI analyses a recorded interview, and it requires annual reporting on whether the data discloses racial bias where an employer relies solely on an AI analysis.
That word solely is doing a great deal of work, and it is the same seam this research keeps finding. A duty that attaches only to fully automated decisions attaches to almost nothing, because almost every consequential decision has a person somewhere in it. Quebec’s own regulator makes the identical point about its own province’s provision, which is set out at the Montreal page.
A third Illinois statute is worth knowing for any audience with a clinical or wellbeing function: the Wellness and Oversight for Psychological Resources Act, in force since 1 August 2025, bars AI from generating therapeutic recommendations or treatment plans without review and approval by the licensed professional.
Adoption without adaptation
The United States Census Bureau runs a business survey with an artificial intelligence supplement, reported by state, and it asks adopters a question almost nobody else asks: what did you change in order to use it. The most common answer among firms using AI is nothing at all.
That is drift with a federal statistical agency behind it. The tool arrives, the process stays as it was, and nobody decides anything. The argument is at drift versus design.
Who books this in Chicago, and who should not
Boards and executive committees, HR and talent leadership, association annual meetings, and the insurance, logistics, manufacturing and professional services firms the city is built on. Framed as Illinois rather than as city law, because that is what the instruments are.
He is the wrong choice for a session on how to comply, which needs employment counsel. This one asks the question compliance cannot: which decisions here require judgement somebody still has.
The three keynotes a Chicago room can book
Keynotes run 30 to 90 minutes, in person or virtual. A 30-minute main-stage version of each talk is available for conferences; the full argument needs 40 or more. The sector examples change for the room; the argument does not. All three, with the showreel, are at keynotes, and the programme copy is at the speaker pack.
Drift versus Design
Drift versus Design: why most organisations hand their judgement to AI without deciding to, and how to design your way through instead.
Most organisations are adopting AI by drift: a thousand reasonable decisions that add up to judgement nobody chose to give away. Rahim Hirji, author of SuperSkills, shows leaders which mode they are running, where AI sharpens judgement and where it weakens it, and hands them the controls.
We Are Superheroes
We Are Superheroes: AI is the suit. The human decides.
AI makes everyone faster, stronger and more capable. It does not decide; people do. Through a family story across four generations and three continents, Rahim Hirji hands the audience the seven human skills that grow more valuable as the tools spread. They arrive thinking AI is the story and leave knowing they are.
WTH (What the Human)
WTH (What the Human): a live test of a board's own judgement.
Business is being rewired as AI arrives, and human judgement is leaving with it. In three acts, Rahim Hirji shows a board what AI is changing in how organisations run, then ends with a live test of the board's own judgement, in the room and in real time. Nobody forgets the result.
Where these sessions happen in Chicago
- McCormick Place, Near South Side
- 2.6 million square feet of exhibit space, the largest convention centre in North America, with the Skyline Ballroom at 100,000 square feet and the Arie Crown Theater seating 4,188. A raked theatre at that scale is rare and it changes what a keynote can be.
- Navy Pier and the Aon Grand Ballroom
- Lakefront, domed, and a different register entirely from McCormick. Right for an evening or an awards format, harder for a working session.
- The Loop and LaSalle Street
- Where the financial, legal and professional services audience actually sits. Hotel ballrooms rather than purpose-built conference floors, so settle the room shape early.
One local platform worth knowing: the Executives’ Club of Chicago runs an annual AI summit in February, which is the most on-thesis stage in the city for this argument. On seasonality, the honest answer is that Chicago’s constraint is weather and travel reliability in January and February rather than anything published.
