A Skeptic's View of Using an AI Coach

In a world where technology promises to simplify our lives, how do those of us with ADHD – notorious for our resistance to structure – harness that promise without abandoning our critical thinking or our humanity? Join me for this conversation with my client, Elizabeth Meyer - professor, coach, and self-described AI skeptic, who offers a roadmap for experimenting wisely with AI-powered tools, while staying loyal to our own brains, values, and need for connection. When Elizabeth was first offered the opportunity to sign up for my digital clone, Di AI, she hesitated. Then she did something unexpected - she designed an experiment to put Di AI and herself to the test. Elizabeth brought a scientist’s rigor to the experience – scheduling regular sessions, setting clear goals, and running timers to structure her use, all to observe how the tool impacted her behaviors and mindset. The episode explores:How Elizabeth structured the experiment (including the infamous decision matrix and her “wildly unrealistic expectations”)Surprising (sometimes maddening) moments where AI reflected “stupid common sense” she’d never consideredWhat ghosting an AI tool taught her about the difference between digital and human accountabilityThe unexpected role of values alignment and motivation for us “rebels”Cautionary tales about outsourcing too much trust—or too much of ourselves—to technologyWhy critical thinking and intentionality are the only way these tools ever work for ADHD-ish brainsElizabeth and I share both the wins and the “facepalm” moments, plus an actionable tip sheet for anyone skeptical (or hopeful) about using AI for habit-building and organization.Her pro tip: Judge the tool by the quality of questions it asks youDon’t Miss:Elizabeth’s three-question framework (adapted from Naturalistic Decision-Making) for deciding when and how to engage with AI tools—so you never cede too much power to an algorithm If you’re tired of empty promises from productivity apps—or want a peek at what a scientifically-minded ADHD brain learns from kicking the tires on new tech—this episode is for you.Fun FactElizabeth shared a story about her 15-year-old niece who, when asked where they should go for dinner, responded: “I don’t know. Let me ask Chat.” The future is here and apparently it’s hungry for chatbot inputYour turn! Make it practical: Use Di AI to help implement a tactic you picked up from the podcast, track specific goals, and follow up on progress.Know your “why”: Consider the reason you are looking for accountability and fit AI into your schedule where you need a champion (hello, bookkeeping!) If you haven’t signed up for Di AI yet - what are you waiting for? Here is the link to sign up for free. Grab Elizabeth’s Tip Sheet for making the most of Di AI (or any AI app)About today’s guest:Elizabeth Meyers is an informatics professor, consultant, and owner of Deep Dive Strategies, where she advises early-stage startups and small companies on strategy and product design.Driven by a fascination with how humans navigate complex environments, Elizabeth specializes in Naturalistic Decision Making (NDM), studying how experts make high-stakes choices in real-world settings. As an entrepreneur who respects both human expertise and technology, she blends her deep background in technology and information science to explore how experts interact with AI. Mentioned in this episode:Conditions for intuitive expertise: a failure to disagree. Kahneman D, Klein G. Am Psychol. 2009 Sep;64(6):515-26. doi: 10.1037/a0016755. PMID: 19739881. Naturalistic Decision Making Conference Michael Webb PresentationAdam Mastroianni - “Bag of Words” post on SubstackDALL- E AI image generator </