Golden Rules in the Age of AI

Venture with us, for a moment, to the 1970s—you’re a researcher in graduate school, embarking on a mission to find and create new knowledge. You hop on a bicycle, ride down to the library, and open the Encyclopedia Britannica to begin to sift through the thousands of articles on the dusty shelves. 

Fifty years later, heavy books and browned pages have been swapped for glossy glass screens with infinite amounts of instantaneously available information. The emergence of tools like Alta Vista, the predecessor to Google, allow for a broad search and easy refinement.

Enter a third iteration of the information ecosystem: the age of AI. In just five decades, the human relationship to knowledge and information—how we process and consume it, where it is available, and who can have it—has totally transformed. Dennis Chookaszian, MBA ’68, is a Booth alumnus and Adjunct Professor of Strategic Management and puts it plainly: "If you use Google search, you're a dinosaur. Everything should start in AI.” This isn't a provocation; it's a principle he has fully adopted into his thinking, teaching, and daily life.

AI is Chookaszian’s sidekick for any and everything. "I use it about 30 times a day," he says. "There isn't anything I do that I don't do in AI." Why? Because agility, rapid adaptation, and a keen awareness of emerging trends have guided his professional life for decades. AI is no exception. 

Having chaired a slew of boards, mentored startups, and developed executive education coursework for Booth, Chookaszian extends his learn-grow-adapt-evolve mindset and toolbelt to future entrepreneurs and current business leaders. Not one to speak about technology from an arial view, he becomes an active participant in it, viewing it almost as an object for close scientific scrutiny and analysis. 

The Rule of Three

Chookaszian has taught his one-hour AI-focused Corporate Governance course over twenty times in the past year to everyone from private equity firms, to over 1,000 members of the Institute of Internal Auditors, to economically-interested clubs of Booth students. He opens every session with the same set of questions.

Who knows what AI is? About 95% of hands go up. 

Who has tried it? Around 75%.

Who uses it on a weekly basis? About 40%. 

Who uses it ten or more times a day? Very seldom more than 10%. Usually closer to 5%.

This is where the gap becomes apparent. Many people have tried AI, have thrown a few questions at it just to scratch the surface of its capabilities, and then moved on. Significantly less have actually changed the way they live because of it. That, Chookaszian says, is the real pitfall. Because we have been presented with an opportunity to completely rethink our way of going about our lives. 

Certainly, the transition from using the library and the card catalog to mastering an online search engine took years to stick. We are in that same lag period now with AI, and most people don't realize it.
To close every session, Chookaszian offers what he calls his Rule of Three.

Rule 1: AI First. Whatever you would have Googled, start in an AI tool instead. He prefers tools that bundle access to multiple large language models simultaneously to get as broad and thorough a search as possible.

Rule 2: Find the Sasquatch. Hold on—this rule has a backstory. When his granddaughter headed off to summer camp, Chookaszian's daughter asked him and his wife to write letters that could be mailed to her while she was away. Chookaszian opened an AI tool. He typed in: create me a letter about marshmallows, camp songs, camp jokes, and pine boughs, in Hemingway style. The result was three pages weaving together the smell of pine needles, acorns falling on her head, and a joke to tell her bunkmate before bed. It was, he says, amazing. 

Within the beautiful letter, one sentence read: ‘But beware the Sasquatch might kidnap you and drag you into the woods.’  He realized he could not say that to a 10 year old girl and he deleted it from the letter.  As he read it and deleted it from the letter, he baked it into what he knows and teaches about AI: Almost every output has a Sasquatch in it and you have to find an delete or modify it. 

It might be a fabricated citation, a sentence scraped from some dark corner of the web, or a fictional creature threatening a ten-year-old at summer camp. High level corporate attorneys who cited nonexistent cases in their court filings failed to find their sasquatch. "A terrible idea," Chookaszian says, "to not fact-check your own work when you know the tool often has inaccuracies or outright incorrect information." Thus, his second rule is that it is vital to read what AI produces carefully, and to edit its output as you would your own work.

Rule 3: Optimize for Form and Function. Once you have your output and you've identified the Sasquatch, optimize it for function and form to fit the purpose. Function, he explains, is utilizing personal discretion to ensure that the output achieves its intended purpose. Function refers to asking ‘who is this for’ and ‘what does it aim to do’ and then adjusting the output accordingly. Optimizing for form is to use one of the tools that humanize an AI output to produce a completely human sounding result. There are many tools that check to see if an output was written by AI and also many tools to optimize the form by removing the “AI speak”. 

In the Classroom, He Is the Sasquatch

Chookaszian doesn't just teach these rules. He embodies them in real time. He expects his students to keep their computers open during class and to fact-check him as he speaks. If something he says doesn’t hold up, he expects to see a raised hand. It has happened more than once, and he says he has learned a tremendous amount from a student researching and correcting him in class.

"In those situations, I'm the Sasquatch," he says. Everyone has gaps, and everyone makes mistakes. The point is to stay curious enough to find them.

He brings the same energy into the boardroom. Chookaszian shows up to board meetings with a four-screen folding computer setup, an AI tool open on one side and meeting materials on the other. When someone says something, he checks it. Many of his fellow board members after seeing the setup immediately purchase a similar one. There are some, however, who believe it is disrespectful to others in the room to have the computer open.  

He believes that they're behind the times, and meetings are much more effective if everyone is constantly reviewing and adding new input.

Still at the Beginning

The flaws in AI are, however, not a reason to distrust the technology, rather a reason to stay engaged with it. When AI hands you something genuinely useful and asks you to bring only your judgment, edits, and critical thinking to the output, it amplifies what you already know how to do. It does not replace the need to know how to do it.

The tension between AI's capability and the human element that is necessary to use it well is the idea behind the Center for Applied Artificial Intelligence (CAAI). The work happening at CAAI is not about AI for its own sake—it’s about understanding where and how it can be applied to create real, meaningful change across healthcare, policy, business and the everyday applications that shape how people live.

Chookaszian has spent decades watching new technologies arrive and watching organizations fumble the transition. His advice, distilled to its simplest form, is this: start in AI, find the Sasquatch, and optimize for form and function. Do that consistently, and it will change how your personal and work life for the better.

He's not waiting for some future version of AI to arrive, because the tools available right now already change everything for people willing to use them.

Dennis Chookaszian is a Booth alumnus and Adjunct Professor of Strategic Management. He has served on the boards of over one hundred organizations, including four AI companies, and has taught Corporate Governance at Chicago Booth for 21 years.