Brain Tricks
Notice autopilot, blind spots, and the pull of an answer you already want to believe.
Better Questions. Stronger Judgment. Smarter AI Decisions.
Let AI expand
your thinking.
Keep your judgment.
Ask agAIn
Unlocking Better Judgment in the Age of AI
For leaders, entrepreneurs, and curious people who want to use AI thoughtfully and make decisions they can stand behind.
Advance reader edition · October 2026
BETTER QUESTIONS.STRONGER JUDGMENT.
THE QUESTION BEHIND THE BOOK
When an answer feels right,
what makes it reliable?
Our minds take shortcuts. AI can make those shortcuts faster, smoother, and harder to notice.
Ask agAIn explores how confidence, attention, assumptions, and persuasive answers shape the way we decide. Dr. Cherry makes the thinking practical, with stories, research, and questions you can use in real work.
You don’t have to check everything. Learn to check the part that matters.
What the Tool Is Actually Doing
Understand changing answers, second opinions, and the limits of machine confidence.
Building Judgment
Bring human context, accountability, and the right questions back into the decision.
THE ASK PRACTICE
Three letters.
A pause that
changes the question.
A practical way to examine an AI answer before you act on it. Match the depth of your check to the stakes.
What am I assuming?
Try this in your AI tool
“What in my question might be an assumption?”
From Appendix A, ASK at a Glance
THE ADVANCE
READER CIRCLE
READ IT. REFLECT. ASK AGAIN.
Be part of the book’s
next chapter.
This October 2026 edition is a confidential review draft. Invited readers can download the book and share how it lands. A few thoughtful sentences are plenty.
Download the review PDFConfidential review copy. Please do not share or distribute.
YOUR READER RESPONSE
What stayed
with you?
I’m interested in how this book lands with you as a reader. What made you pause? What might you do differently? What needs more clarity?
Dr. Cherry
BEYOND THE LAST PAGE
Give better judgment
a place in your work.
The book is a beginning. Upcoming learning experiences will bring the ASK practice into everyday AI decisions, conversations, and leadership.
Live classes
Practice spotting assumptions, checking sources, and identifying the key piece in real situations.
Video learning
Short lessons and guided reflections that bring the ideas from the book into your day.
Speaking & team workshops
Bring the conversation about AI and human judgment to your leadership team, organization, or event.
Be first to hear what’s next.
Tell me what interests you. Dates and details will follow.