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 working together with the right support. Understanding how to evaluate a digital coach is about understanding what working together with AI actually means for your brain.
When Elizabeth was first offered the opportunity to sign up for my digital coach, 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. She approached the digital coach the way a true ADHD accountability partner would: with intentionality and critical thinking.
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 considered
What ghosting a digital coach taught her about the difference between digital and human accountability—and why a real ADHD accountability partner matters
The unexpected role of values alignment and motivation for us “rebels”
Cautionary tales about outsourcing too much trust—or too much of ourselves—to technology
Why critical thinking and intentionality are the only way these tools ever work for ADHD-ish brains
Elizabeth and I share both the wins and the “facepalm” moments, plus an actionable tip sheet for anyone skeptical (or hopeful) about working together with AI for habit-building and organization.
Her pro tip: Judge the tool by the quality of questions it asks you
Don’t Miss:
Elizabeth’s three-question framework (adapted from Naturalistic Decision-Making) for deciding when and how to engage with digital coach tools—so you never cede too much power to an algorithm. This framework helps you decide if working together with AI serves your actual needs.
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 Fact
Elizabeth 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 input
Your turn!
Make it practical: Use a digital coach to help implement a tactic you picked up from the podcast, track specific goals, and follow up on progress. Think of it as working together with technology.
Know your “why”: Consider the reason you are looking for an ADHD accountability partner and fit AI into your schedule where you need a champion (hello, bookkeeping!). Is a digital coach the right fit for your specific need?
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 a digital coach 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 Presentation
Adam Mastroianni - “Bag of Words” post on Substack
Ep #281: Find Your Flow: 3 Focus Days Models for ADHD Brains
Ep #212: Get More Done: How to Focus with ADHD & Take Real Action
Your ADHD-ish™ host, Diann Wingert
Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive.
Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance.
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© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
