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Free minibook · PDF, 21 pages
What Five Champions Learned When a Machine Joined Their Game, and a Five-Step Method for Bringing AI Into Expert Work
In 2004, Ken Jennings won 74 straight games of Jeopardy! In February 2011 he played IBM's Watson, and Watson won. Read the rest of what Jennings and the other champions in this free minibook said and did, and you find experts studying exactly where a machine was better, where it wasn't and what they could do about it.
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By Todd Hagopian, who has led business transformations at Berkshire Hathaway, Illinois Tool Works and Whirlpool.
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Who it's for
Leaders of teams of experts, such as estimators, quoters, analysts, planners and engineers, whose company is bringing in an AI tool or hearing a vendor pitch one. Test it on your own past work before you trust it, find its edge and its errors, design who does what, train your people with it, then probe it for failures on purpose and decide which decisions people own.
Not for you if decisions governed by safety rules, regulation or law, or decisions about people such as hiring, pay or discipline. The book makes no prediction about what AI will do next. It shows you how to measure what it does now.
What you'll learn
- Test It on Your Own Board
- Find Its Real Edge
- Design the Partnership
- Train With It
- Probe It and Own the Result
Plus a final action plan and a worksheet you can use the same week.
Key takeaways
- Test it on your own board. The demo ran on the vendor's cases; backtest on past work where you already know the right answer.
- Speed is one edge. Map the others, and the failure modes, case by case, especially confident misses.
- Design the partnership from your map: where the tool is strong it drafts and a person reviews. Measure net time saved.
- Train with it, not just beside it: study the cases where the tool and your experts disagree.
- Probe it on hard cases on purpose, write down which decisions people own and retest after every vendor update.
From the book
In 2004, Ken Jennings won 74 straight games of Jeopardy! and more than $2.5 million. On November 30, 2004, he finally lost, on a Final Jeopardy! clue he missed.
In February 2011, he played again, alongside Brad Rutter, the show's other great champion. Their opponent was IBM's Watson. Watson won.
Jennings wrote afterward: "'Quiz show contestant' may be the first job made redundant by Watson, but I'm sure it won't be the last."
It's easy to read that as a prophecy. Read the rest of what Jennings wrote, and what the other champions in this book said and did, and you find something more useful: experts studying exactly where a machine was better, where it wasn't and what they could do about it.
The board is the same: your customers, your problems, your standards. The opponent is new. This book is about learning to play.
Todd Hagopian, Same Board, New Opponent, from the prologue "Seventy-Four Games"
Frequently asked questions
The AI demo was impressive. Why test it again?
Because the demo ran on the vendor's cases, and the tool will change. Test it on your own past work, where you know the right answer, against what your experts actually did. Then retest on a schedule.
Should the AI tool do the work, or should our experts?
Neither, as a blanket rule. Decide case by case from your map of the tool's edge and its errors. Where the tool is strong, it drafts and a person reviews.
Once it's working, can't people just use it?
They can, and slowly lose the skill the tool can't replace. Or they can use it to get better. The difference is a habit: regularly studying the cases where the tool and your experts disagree, and asking why.
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Read moreRelated reading on the blog
- Beyond the Pilot: The 3-A Method for AI 2026
- Pattern Reader Intelligence vs Predictive Analytics
- 70% Rule for Robots: 2026 AI Guardrails
Go further
Stagnation Assassin: The Anti-Consultant Manifesto is about the bigger fight: the conditions that make companies decay from the inside, the team you need to fight them and the tools to keep a recovered business moving. It's available now. Todd's next book, 10-Minute Transformation, is out February 23, 2027.
The full library
Two ways to get it. Preorder now and it ships on release. Or buy on launch day, February 23, 2027, and get three free audiobooks (10-Minute Transformation, Stagnation Assassin and The Unfair Advantage) plus the full minibook library, on the honor system. Preorders don't include the launch-day bonuses.
About the author
Todd Hagopian, The Stagnation Assassin, is VP of Product Strategy and Marketing. He has led business transformations at Berkshire Hathaway, Illinois Tool Works, and Whirlpool Corporation, with $3B+ shareholder value across five turnarounds. He speaks to leadership teams on business transformation, turnarounds, and breaking stagnation.