EP 275 "Do I Trust Myself?" Grace Gravestock on the Real Reason AI Adoption Stalls
Release Date: 07/29/2026
EP281 Your Team's Nervous System Is Infrastructure - Sira Laurel on Load-Bearing Trust
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Most of the leaders Sira Laurel works with look like they're winning. Inside, they're exhausted. Sira is an executive coach and facilitator who works on leadership, organizational design, cognitive load, trust and nervous system capacity. She has watched organizations get very good at making work faster while getting worse at deciding what the speed is for. AI raises the stakes on that question. Her starting point is that capacity covers far more than time. It includes attention, decision-making, emotional bandwidth and creative energy. A tool can hand back hours on the calendar while draining...
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EP280 Faster Than a Generation - Ian Alden Russell on Change That Outruns Us
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This episode skips the tools, the prompts, and the latest model release. It goes somewhere more philosophical. started out as an archaeologist and anthropologist. He was the kid who loved museums and Indiana Jones. Since then he has worked across history, contemporary art and culture in Dublin, Istanbul, Beijing, Hong Kong, Pittsburgh and Doha. Now he works as a strategist helping organizations make sense of complexity and line up around change. His starting point is that change itself is old news. Humanity has absorbed huge technological shifts again and again. The new part is the speed....
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EP279 How higher ed moves from AI interest to governed use with James Hutson
AI Literacy for Entrepreneurs
A previous president from Lindenwood University (a former IBM executive) stands up in town halls and tells people he uses Claude - that it helped him organize the financial report. HR follows and says they used Gemini for an employee questionnaire. Then James Hutson PhD. goes and asks employees whether they understood that as permission. The answer? 'No. The policy says I'll get fired if I use it.' That gap is the subject of this episode. James is Senior Professor and Director of AI-Enabled Academic Transformation at Lindenwood University, with two PhDs - the first in art history, the second...
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EP278 AI Governance in Higher Ed with Dr. Eugene Chan
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EP277 Is AI Going to Take the Gift of Failure Away? asks Julie Cole
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EP276 Your AI Strategy Is a Hammer. Where's the Nail? - with David Cohen
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EP 275 "Do I Trust Myself?" Grace Gravestock on the Real Reason AI Adoption Stalls
AI Literacy for Entrepreneurs
Episode description Everyone's arguing about whether AI can be trusted. Almost nobody's asking the harder question underneath it. Grace Gravestock has spent more than twenty years leading change management on some of the highest-profile technology projects around - including the team that set the stage for the $67B Dell EMC integration. Her verdict on why AI pilots stall is unsentimental: it's the same reason ERP stalled, and CRM before that. People aren't using the technology the way it was intended. You can have the best tools in the world, and if people don't use them, it doesn't matter....
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EP 274 The Human OS - AI Adoption With Curiosity, Safety, and Monday Ease ft. Melissa Penton
AI Literacy for Entrepreneurs
In the final episode of the Podcast-to-Book series, host sits down with change leader and AI education lead (Sun Life) for a human-first conversation about what actually makes AI adoption work. They talk productivity vs room-for-life, why one-prompt culture is snake oil, the shift from prompt engineering to context engineering, and the simplest enterprise question that changes everything: “What would make Monday easier for employees?” Episode summary Susan closes out the Podcast-to-Book sprint with a conversation that feels like the point of the whole series: AI isn’t a tool problem....
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273 - Future-proofing your organization through continuing AI literacy
AI Literacy for Entrepreneurs
Most companies do a few AI trainings, run some pilots, and then stall. In this episode, host argues the only real future-proofing strategy is continuous AI literacy. She breaks down what “continuous literacy” actually includes (skill, judgment, workflow, norms), the predictable failure modes of the AI literacy divide, and a simple flywheel you can run monthly so capability keeps compounding. Episode summary Susan opens with a familiar pattern: a burst of AI excitement, a deck called “AI Strategy 2025” a few clever workflows… and then reality hits. Tools change. Policies shift....
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EP 272 - Mindset, Sales, and AI That Actually Helps with Gazzy Amin
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Host sits down with sales strategist , founder of Sales Beyond Scripts, to talk about the real ways AI is changing revenue, planning, and scale. They cover AI as a thinking partner, how to use it across departments in a small business, why audits matter more than hype, and how mindset quietly determines whether you treat AI as a threat or an advantage. Episode summary This episode is part of Susan’s 30-episodes-in-30-days “podcast to book” sprint for Swan Dive Backwards. Susan and Gazzy zoom in on the selling process first. Then they zoom out to the whole business. They talk about three...
info_outlineEpisode description
Everyone's arguing about whether AI can be trusted. Almost nobody's asking the harder question underneath it.
Grace Gravestock has spent more than twenty years leading change management on some of the highest-profile technology projects around - including the team that set the stage for the $67B Dell EMC integration. Her verdict on why AI pilots stall is unsentimental: it's the same reason ERP stalled, and CRM before that. People aren't using the technology the way it was intended. You can have the best tools in the world, and if people don't use them, it doesn't matter.
But the conversation turns when Susan brings up the trust deficit - the LinkedIn feeds full of complaints about AI slop, the comment sections litigating whether a video is real. Grace flips the question entirely: the crisis isn't whether we trust the machine. It's whether we still trust our own judgment.
Along the way: the Mac Mini that sat unused for months, why the longest-tenured experts are your real bottleneck, why young people are hitting the brakes hardest, and the one change that rescued a technology rollout that had already failed.
About Grace Gravestock
Grace Gravestock is a change management leader with more than twenty years on large-scale technology projects. She was part of the team that set the stage for the $67B Dell EMC integration, one of the largest tech mergers in history. Her work spans Deloitte, Dell, and Warner Brothers, plus years consulting inside the utility sector. She got her start in the UK on a government services rollout that touched every citizen in the country, at the front edge of the eGov boom. She's now turning that expertise toward AI adoption, and is writing Three Secrets to Making Change Fun and Easy.
What we get into
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(01:31) From a UK-wide government rollout to AI adoption - Grace's twenty-year arc
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(03:13) Why AI pilots are failing, and why the answer is boringly familiar
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(04:56) Why training isn't the root - and what has to happen before it
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(06:02) The surprise: young people are putting the brakes on hardest and fastest
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(07:10) Secret one - we get to choose. Why agency is the whole ballgame
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(08:23) Why your longest-tenured experts are the real bottleneck (and why you need them anyway)
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(10:35) The Mac Mini that sat there for months
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(11:47) Susan on being a ChatGPT person who barely opened Claude
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(12:29) "Am I training my own replacement?" - the fear leadership keeps answering wrong
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(13:22) Choosing to become more human rather than less
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(14:30) Monday morning heart attacks, and the work people don't want to go back to
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(16:50) The people who keep their jobs will be the ones who know how to orchestrate
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(18:48) How leaders should communicate when they don't have all the answers - WIIFM radio
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(20:06) The single change that rescued a failed rollout: executive bonuses
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(21:28) Two utilities, same state, wildly different outcomes
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(23:36) "We are not planning on cutting jobs. We're planning to 10x our results."
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(25:06) The trust deficit, LinkedIn, and the inauthenticity problem
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(28:35) The question that reframes everything: do I trust myself?
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(30:09) What leaders can actually do this week
Quotes
"You can have the best technology, and if people don't use it, it really doesn't matter." - Grace Gravestock
"The biggest reason people hate change and fear change is because it potentially means instability." - Grace Gravestock
"We get to choose how, not if, we're going to engage. AI is not going away." - Grace Gravestock
"There's no such thing as living in your glass house and throwing stones. You've got to be in the trenches." - Grace Gravestock
"Here's the biggest thing that we don't talk about, Susan. Do I trust myself? Do I trust myself to make my own decisions and use my own brain?" - Grace Gravestock
"The people that have jobs are going to be the ones that know how to orchestrate." - Grace Gravestock
Grace's three secrets
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Consciously choose. Change begins as an individual decision, not an org chart mandate.
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Align. Does this choice fit who you are and where you're going?
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Be open to new ways. New tools, new working patterns, new definitions of the job.
Applied to AI: You do get to choose how, when, and where.
Resources
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Grace's book waitlist and a short video on the three secrets: funandeasychange.com
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Connect with Grace on LinkedIn: linkedin.com/in/ggravestock
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Susan's book, Swan Dive Backwards: wearenorthlightai.com/swan-dive-backwards
If this episode landed, read this next in Swan Dive Backwards: Chapter 8, Culture as the OS - the trust recession, psychological safety, and why adoption questions are almost never technical ones. And Chapter 3, The AI Literacy Divide, for the fear Grace names from the change management side.
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