Hosts Philip Maymin and Dr. Jie Tao, from Fairfield Dolan and the University’s new AI & Tech Institute, show how to move beyond “prompt and pray” toward reliable, structured results with AI. Hear why most one-shot chats fall short, how to “flip the switch” so AI asks clarifying questions, and why treating AI like a brilliant, but clueless, intern leads to better outcomes. You’ll learn the four-part “AI job brief” approach (including role and audience), when to iterate, and how to make structured prompts statistically inevitable—rather than hopeful guesses.

Learn more about Fairfield Dolan's AI and Technology Institute.

Chapters: 00:00 – Welcome, hosts, and episode focus 01:33 – A perfect brief vs. a painful miss: instructions matter 02:00 – What “prompt and pray” is—and why it fails 03:09 – One-shot chats, search habits, and better use of AI 05:17 – The generalist-doctor analogy: give problem context 08:36 – Flip the Q&A pattern: make AI ask follow-ups 15:15 – Iterate your prompt like drafts (not one and done) 16:15 – The backspace rule: why iteration beats perfection 17:01 – Structured prompts part 1: define the role 19:30 – Structured prompts part 2: set the audience 26:59 – Memory windows: keep briefs lean and focused 34:53 – Working in steps: sequencing tasks with RAFT 41:56 – From “pray” to “statistically inevitable” results