The AI Coach: Accountability and Behavioral Design

This week, we advance our series, The AI-Powered Professional, by exploring the "AI Coach." We'll dive into how AI is moving beyond simple task automation to becoming a force multiplier for personal transformation, focusing on "Accountability and Behavioral Design." We'll explore how these tools leverage data, psychological principles, and customized nudges to help us close the intention-action gap, consistently execute goals, and build lasting, productive habits. (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/152 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing The AI Coach: Accountability and Behavioral Design from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | The AI Coach: Accountability and Behavioral Design Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | The AI Coach: Accountability and Behavioral Design Resources we mention, including links to them, will be provided here. Please listen to the episode for context. Loss aversion Stickk Positive reinforcement ELIZA Raw Text Transcript Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More Voiceover Artist | 00:00 Are you ready to manage your work and personal world better to live a more fulfilling, productive life? Then you've come to the right place. Welcome to ProductivityCast, the weekly show about all things personal productivity. Here are your hosts, Ray Sidney Smith and Augusto Pinaud with Francis Wade and Art Gelwicks. Ray Sidney Smith | 00:17 Welcome back, everybody, to Productivity Cast, the weekly show about all things personal productivity. I'm Ray Sidney Smith. Augusto Pinaud | 00:24 And I'm Augusto Pinaud. Francis Wade | 00:25 I'm Francis Wade. Art Gelwicks | 00:26 And I'm Art Gelwicks. Ray Sidney Smith | 00:27 And welcome to our listeners to this episode of ProductivityCast. This week, we basically advance ourselves in our series, our ongoing series, The AI-Powered Professional. And we're going to be exploring today basically everything that we want to dive into how AI can move beyond simple task automation, simple task completion, to more of helping you with personal development, but just accountability and behavioral design. So let's talk about some of the tools we can use, some of the principles behind it, And we're going to start off with really discussing why we need... Technology to coach us in the first place. So Let's go ahead and dive into what the problem is, and then we can opine on whether or not AI can help us. So why would you need an AI coach? Who cares about having an AI coach? Francis Wade | 01:22 I had a friend who was a master's in exercise physiology. Shed clients. She was training them and she was meeting them at the gym every morning and She eventually gave it up because she said that with her Exercise Physiology Masters She was doing nothing more than bringing them all to bed. And delivering them to the gym. And standing by while they exercise. In other words, she wasn't actually applying anything she learned. All she was doing was being an accomplished nanny. It illustrates the reason why we do need this kind of assistance is because we're not, left to our own devices, we're not reliable. And there's a whole part of the coaching experience or delivering coaching experience That really is just about reminding on the one side and then holding accountable on the other. All the words. A lot of it has to do with just creating structure. And if that could be outsourced to AI, then, hey, Hold to us. Art Gelwicks | 02:22 AI coaching to me is... Better defined as coaching light. It doesn't carry any of the gravitas of an actual human coach. You can ignore an AI if it's telling you something that you don't really want to do? Yeah, it'll prompt you. It'll bug you. It can do all the things, but it's really... It's a way to get those reminders without the confrontation possibility. As part of the exercise. And I've seen people start to use AI in that kind of coaching approach and seen applications where they start to integrate this AI reminder into a process to encourage you to go through. And that's nice, and that's convenient. But it is still a device. So... I would definitely qualify AI as... Coaching light. A true coach is going to look at you and go, Yeah, but you can ignore that. You can't ignore me. Ray Sidney Smith | 03:17 Yeah. So stepping back to the core problem, which is that humans are really good at... Accomplishing things, utilizing accountability as one of the motivational paradigms. So we don't want to feel like we have reputational harm by not completing something. And so we can use accountability for that purpose. As I've talked about before, we have four layers of accountability that we can really think about. And the framework is that you have kind of self-accountability where you can keep yourself accountable to do something. You can have one-to-one accountability, whether that's a friend, a family member, or a professional. A professional coach, professional trainer, service provider and you are having them hold you accountable to do that thing, then you could step up to a group of then you can step up to what I call public accountability, where you claim publicly you're going to do something so that a vast majority of people beyond your close network know about you doing that thing. And so with these four layers of accountability, we know that we can get things done. And with AI coaching, we're really in that one-to-one accountability space. And I, like Art, really fundamentally believe that right now, at least as the technology is evolving, and how it's designed. Can't really replace a human coach. It can fill in gaps really well. I think that humans have the challenge of self-reporting We tend to be poor judges of our own consistency. We are not objective. And the AI can provide that objective, nonjudgmental, data to you on your actual behavior versus your stated goals. And since we have a human coach. Has a limited ability. To be available? The AI coach can basically provide nudges To be at a precise moment and place so you can have it monitor where you are, when you are and say, here goes this thing that you said you wanted to do and help you define whether or not you want to deviate from that plan. So say that I am in a particular application at work and I all of a sudden go to Instagram. The AI coach can now say, hey, Ray, I noticed that you went to Instagram instead of your work email. Is this a distraction? And now it can help just by that little nudge, helped me move myself toward the future. Planned activity as opposed to the unplanned activity that I was planning. We've had this indeterministic software for some time, but now we have AI versions of this, which is that it can block. Tools completely so that you can't go to a particular And that's a form of kind of coaching light, as Art was saying as well. So there's this notion that we're going to be able to do this. Providing a boundary to our access to things and that helps us stay on the pathway. So there's a lot of different reasons I think that can help us here in the coaching space but it's not a human. And even when we get to the concept of embodied AI, where we have robotics that are humanoid or humanoid-like robots, that then have AI embedded in them and they can be in your physical presence, I still don't see them as being the same thing as a full-blooded, bag-of-meat-and-bones person in front of you with the potential reputational harm of not showing up to do the thing. There is just something... Human to human about that I don't think a robot's really going to replace. Francis Wade | 06:54 Interesting you say that because my experience is that an AI coach, and I've not used the Actually, I have used an AI coach for my writing. But an AI coach... Is somewhere between just a Blind reminder, an alarm clock. On steroids. And a real person. It's moved up into that realm. But it's not doing the moving. I am. So what I'm doing is essentially I'm empowering people A voice. An automatic voice. To be more human than an alarm clock. And I think I could do some of the things you're talking about if I were to do it. I'm sure you've heard about the ideas around setting up a countermeasure mechanisms that involve creating a punishment for yourself if you don't. Accomplished the task. And I think there was a website. Allowed you to set up these punishments. And it was extremely effective. So there's nothing to stop us from having an AI persona. That For example, we say, if I don't stick to my diet this week, AI, you have the full permission to go into my... For the record. And tweet out to the whole world that you're punishing me in public for not... And you do something that's that I don't want you to do. And like, you praise up. Political party that I want to have no part of or something like that. But I sort of a punishment that creates a bit of a game that may not be necessarily dangerous or damaging in the long term, but it's at least somewhat annoying. I think I would respond to a game like that because I don't want my account tweeting out support for a party that I don't support. If that were the punishment, That would be enough motivation for me. ...

The AI Learning Partner: Socratic Skill Acquisition and Rapid Mastery

Stop treating AI like a simple search engine and start using it as your own personalized, tireless mentor. This episode explores how to leverage AI-powered tools to bridge knowledge gaps, master complex skills, and accelerate your professional growth through the science of adult learning. (If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/151 for clickable links and the full show notes and transcript of this cast.) Enjoy! Give us feedback! And, thanks for listening! If you'd like to continue discussing The AI Learning Partner: Socratic Skill Acquisition and Rapid Mastery from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post). In this Cast | The AI Learning Partner: Socratic Skill Acquisition and Rapid Mastery Ray Sidney-Smith Augusto Pinaud Art Gelwicks Francis Wade Show Notes | The AI Learning Partner: Socratic Skill Acquisition and Rapid Mastery Resources we mention, including links to them, will be provided here. Please listen to the episode for context. Andragogy vs Pedagogy Socratic Method Comprehensible Input / Comprehensible Output (in the context of language learning but generalizable) "The illiterate of the 21st century will not be those who cannot read or write, but those who cannot learn, unlearn, and relearn." ~ Alvin Toffler Future Shock by Alvin Toffler The Ultimate Deliberate Practice Guide: How to Be the Best  Strat Cinema (by Francis Wade) Raw Text Transcript Raw, unedited and machine-produced text transcript so there may be substantial errors, but you can search for specific points in the episode to jump to, or to reference back to at a later date and time, by keywords or key phrases. The time coding is mm:ss (e.g., 0:04 starts at 4 seconds into the cast’s audio). Read More The AI Learning Partner: Socratic Skill Acquisition and Rapid Mastery Raymond Sidney-Smith | 00:00 Welcome back, everybody, to Productivity Cast, the weekly show about all things personal productivity. I'm Ray Sidney-Smith. Augusto Pinaud | 00:06 And I'm Augusto Pinar. Francis Wade | 00:07 And I'm Francis. Raymond | 00:08 Raymond | 00:08 Wade. Welcome, gentlemen, and welcome to our listeners to today's episode. Today, we're going to be continuing our AI-powered professional series, And in this particular episode, we're going to focus in on how AI is... Helping people become better learners. Basically, how these tools are transforming personal and professional development. And so we're going to be talking about passive consumption, how we use maybe some Socratic method, and how we can do all of this through the creation of AI acting really as a personalized mentor tool. To basically challenge our understanding, accelerate our learning curve, and help us achieve proficiency, hopefully faster than before. And so let's talk about what traditional learning really looks like, and then we'll Talk about what the... Problems are in that space that we're trying to solve for when we're utilizing AI. Francis | 01:09 So the traditional model is that you sit down and receive knowledge from someone else. That there's an expert. Behind the scenes. But what's happening now is way more fluid than that. It's that. I'm somehow reaching out to an entity and it's reaching out back to me in real time. And it's an AI entity.  So no experience is give and take between you Something that's really smart. And where I am. And this give and take is not Obviously, it's not one directional, but It changes over time because I've noticed that cloud for example, is becoming better at finding stuff for me or teaching me stuff.  So it's like having this flexible space in which I'm being exposed to more things, I'm learning more things, I'm remembering more things. Because it's reminding me of more things. I'm accessing more options. And in so doing, I'm becoming a better professional. In my case, I'm thinking in particular of writing. I'm becoming a better writer. It couldn't have happened with a human being. The way it's happening with AI. And for the last year and a half, I'm really grateful for it because this kind of flexible space is Absolutely making me a better professional.  So it's again, It doesn't compare to anything that I've experienced before. So it's something that's brand new and it's evolving. I. Raymond | 02:38 Do, too. Augusto | 02:39 Hello. It is interesting. I'm going to talk about two cases that I recommend. For social media for artificial intelligence. One is I sometimes work with clients who have beaten up. Okay, beaten up as a child, beaten up as an early adult, beaten up. And one of the things that AI produce a different experience. Delusional, but a different experience is that AI will try to make you feel good. And I have recommended to a couple of my clients, go and have a glass of wine and a chat with your chat GPT. Okay, feel good. Because Feeling good, it's very important for productivity. It's very important for learning. It's very important. If you go, okay, I'm going to study this book. And you get into that, I'm going to study the book. But then you go like, okay, well... I don't know how to learn or I can't get into this material. The learning, the growing is very hard. Feel nice.  So that's one thing. But the second is how much Really? You can adventure. Into new topics, even if you don't want to master them. Okay. I remember Good day. Before Google, yes, because I'm that old. Okay. Where if you wanted to repair your car, okay, your best hope was to go to AutoZone or the equivalent and find a Hanes manual. Okay. And that thing was like the golden source. You could have every screw of that car had was on that manual. It was incredible. Then came YouTube and we asked how we did it before YouTube where you can see the video. Now it's even better. I have a chat for every vehicle we have in our house. Okay? And I can go and ask, not for, okay, how do you fix, no, for this specific model of this specific year of this. And it saves even more time. I enjoy a glass of wine once in a while. I'm very bad at it. Okay? According to a friend of mine, the reason is I don't drink enough wine. Okay? And if you get very good at it, you need to drink enough wine. I fail. Okay. But this is what is interesting. I've been putting into ChatGPT, okay, the wines that I enjoy. Okay. When I, and, What happened the other night, I was having dinner with some friends. We were in their house, and a friend of mine pulled three bottles of wine. I said, pick one. In the past, I will have picked based on the label. Guilty of charge. I know nothing about it. This time, I pull my phone, take a screenshot or a picture of the three labels and say, what matched my profile? And it picked something completely different to what I was going to pick. But It was actually fitting to the profile. It was a glass of wine that I enjoy because in the past what happened is I get the glass of wine and No, this one was. You can go from the mundane And you can really go with this. To the expert level. I was having a work issue with a VDI. For the people who don't know what a VDI is, it's a virtual desktop interface. And I basically have a client who gives me this VDI to do work with them. Fantastic. Except that I could not make it work for what I wanted to make it work. Chat GPT to the rescue? No. Okay, I went put all the details blah and it says the problem is you are trying it was an audio issue you are trying to make This on your iPad. The solution is try to remove I remove one of the layers it worked better and then I went and bought a And they're flying. Problem solved. The problem is the machine and the VDI cannot go and convert the audio to the VDI audio, to the iPad audio, to Bluetooth. Great. And remove two of those layers and problem solved. But these were things that in order to get to those conclusions, the number of trial and errors And the time that you need was... Among us. And now you can get those answers with two or three good prompts very quick. That bring me to the last point I'm going to make. I remember the first time I read Alan Toffer sentence saying, The analfabets of the future will be those who are unable to learn and unlearn. If he will be alive today, he will say that alphabets of the future will be those who can make prompts. And this is something when people say, then AI is going to take our work and the world and all this. Yes, it's going to change it. No question about it. And Terminator will be in the right of the corner. That said. The right prompt will really make this tool A tool? And if you don't learn how to do prompt and just think you can do what you did with Google, You are. Much likely dead in the water. Raymond | 07:48 There are a couple of things that I think AI can help with here in terms of learning. When you have full agency over your life, the way in which you learn is going to be different. When you have an employer who may be asking you to learn as you onboard into a new company, you may have to watch a whole bunch of learning videos to onboard into the company. That is a fundamentally different kind of learning than a teacher teaching you, a professor teaching you, a topic so that you can get a degree and move on in the education system.  So we need to think about the way in which we are thinking about learning as adults and that I think that perspective alone changes when you start approaching AI as what I talk about as basically being a learning partner. Because this becomes not just, I mean, there's so many different categories. I can go in a lot of different directions, but I will, I'll say that one, just learning on the fly, it becomes this wonderful learning experience....

The Strange Thing Successful CEO Do Before They Fail

Picture a boardroom anywhere in the world. A new strategic plan is about to be built, and it follows a stretch of disappointing results. Someone at the table believes the old plan deserves an honest look before anyone writes a new one. The rest of the room disagrees, and the person leading that resistance is the chief executive.

This scene repeats itself constantly, across industries and continents, in companies large and small. And it repeats for a reason that has surprisingly little to do with the numbers on the page.

Somewhere in that room, someone already knows what went wrong. They stay quiet, and not because they lack nerve. Often the silence exists because the one person who most needs to hear the diagnosis has quietly turned the plan’s failure into a verdict on himself.

This has a name, though it is rarely the name people reach for. It isn’t stubbornness, and it isn’t ego in the casual sense most people mean when they use the word. It’s something closer to fusion: the CEO’s sense of identity has welded itself to the authorship of the plan. Criticizing the plan starts to feel indistinguishable from criticizing the man.

The Instinct to Diagnose the Leader

The common response to a struggling CEO is to assume he needs more self-reflection. That diagnosis feels intuitive, and it is usually wrong.

Executive coaches who work with senior leaders will tell you something consistent: top performers tend to run high on confidence, and sometimes on narcissism. Wins get filed under personal skill. Losses get filed under bad luck, timing, or a market nobody could have predicted. Which means owning a failure takes real effort, precisely because nothing in the leader’s usual operating system asks him to.

So what actually moves a confident leader to let go of a plan he built?

Three well-documented cases suggest an answer, and it isn’t introspection triggered by failure. It’s something closer to a deliberate choice, made from strength rather than crisis.

Garry Ridge spent over two decades running WD-40, and built one of the most studied culture turnarounds in modern business on a simple, command-driven mantra: be brilliant, be brief, be gone. At some point that mantra stopped fitting the company he wanted to build. He later described the shift in five plain words: he couldn’t do it alone.

Alan Mulally took over a struggling Ford and steered it through the 2008 financial crisis without the government bailout its competitors needed. About the plan that made that possible, he said something equally direct: it was bigger than him.

Satya Nadella went a step further at Microsoft. Rather than simply saying the company’s direction wasn’t his alone, he dismantled the senior leadership structure built to run things that way, on the theory that no single person, including the CEO, should hold that much of the answer.

None of these three men were failing when they made that call. Each was already succeeding, with every reason to keep doing exactly what had gotten him there. Yet each one gave up sole ownership of his company’s direction anyway, voluntarily, before a board or a crisis forced the issue.

That timing matters more than it first appears. It suggests the shift isn’t a symptom of failure, something a leader is forced into once the results turn bad. It’s a decision available to any leader, in good times or bad, and the best ones make it deliberately, long before anyone hands them a reason to.

Rejecting a Popular Premise

Ridge, Mulally, and Nadella weren’t managing their egos more skillfully than other executives. They were rejecting an assumption most organizations never examine: that a company’s direction is supposed to be authored by one person at the top, the way a founder might write a mission statement on a napkin and hand it down as scripture.

That assumption carries a flaw most boardrooms never name out loud. A company’s direction isn’t handed down from a single mind, however talented that mind happens to be. It gets surfaced collectively, through the accumulated judgment of the people running the business day to day, closest to the customers and the friction points a CEO rarely sees firsthand. The more a leader treats that direction as personal property, something he built and therefore owns, the more fiercely he will defend it against the one exercise that could actually improve it: an honest post-mortem.

The Same Reflex, Wearing Two Faces

This reflex shows up differently depending on how the last plan went, which is part of why it goes unrecognized so often.

When a leader senses the prior strategy failed, he tends to suppress honest discussion about it. Even a carefully facilitated review can land like an accusation rather than an exercise, and the room adjusts accordingly, softening its language until the review says almost nothing useful at all.

When a leader believes the prior strategy succeeded, the resistance shows up dressed differently, but the underlying mechanism is identical. Success gets defended as proof that nothing needs to change. This is the same instinct that kept a dominant film company comfortable with film long after digital cameras arrived, kept a video rental giant comfortable with physical stores while streaming quietly took over living rooms, and has repeated itself across a long list of once-dominant firms convinced that what worked before would keep working. Confidence in past results becomes the very thing that blocks an organization from spotting the threat forming just outside its field of view.

Failure resists a post-mortem out of self-protection. Success resists it out of certainty. Both come from the same place: a leader who has made the plan’s outcome personal, whichever direction that outcome happened to run.

There is a third variation worth naming, quieter than the other two. Some leaders resist not because the result was clearly good or bad, but because it was ambiguous, and ambiguity is harder to defend than either extreme. A mixed result invites the most debate, and debate is exactly what identity fusion is built to avoid.

What a Colleague Can Actually Do

If you aren’t the top leader, and you sense your CEO is standing in the way of an honest review, pressure rarely works. Direct confrontation tends to trigger the very defensiveness you’re trying to move past, and most people who have tried it once rarely try it the same way twice.

A better move is reframing the role itself. Help your CEO see himself less as the sole author of the company’s direction and more as its chief learner, or its lead experimenter, someone whose job is to keep testing the plan rather than defend it. That single shift in self-perception does more work than any argument about specific numbers ever will.

Ridge, Mulally, and Nadella are useful here, not as inspiration but as evidence. Each one answered the same question at the height of his influence, when nothing outside forced the admission: whose plan is this supposed to be?

Now picture your own CEO hearing that question, in your own boardroom, this week. He is still resisting the post-mortem, and you are still deciding how hard to push. The better question isn’t how hard. It’s which question you ask.

Not a challenge to his judgment. An invitation to a role he likely never chose for himself, and one he remains entirely free to choose now, at whatever stage his company’s story happens to be in.

——————————————-

PS: Five prompts to take this further with an AI assistant

  1. “I lead a team where a senior leader seems to be personalizing a past strategic failure. Help me identify three signs this is happening, based on the psychological pattern described in this article.”
  2. “Using the Ridge, Mulally, and Nadella examples, help me draft a short, low-pressure way to raise the idea of a strategy post-mortem with my own leader, without it sounding like a criticism.”
  3. “Walk me through the difference between a leader resisting a post-mortem out of failure versus resisting one out of past success. Which pattern sounds more like what I’m seeing in my own organization?”
  4. “Help me design a simple post-mortem process for my team’s last strategic plan that treats the findings as collective, not as an evaluation of any one person.”
  5. “If I wanted to reframe my own role from ‘owner of the vision’ to ‘chief learner,’ what would that change about how I lead the next planning cycle? Help me think through three concrete differences.”

Ep 38 – The Bellhop and the Sardines w/Amie Devero

Your company knows that it needs to move quickly once a corporate strategy has been developed, to get the document in the hands of the staff.

But what does it mean to “get it into their hands?” Send them a pdf? Get them to watch a video? Attend a town hall? Attend a briefing from their manager, after she has received her briefing?

This is a massive problem and here today to apply an AI-driven solution is Amie Devero. Tune into this episode to hear from us as we tackle the issue of strategy activation together.

Show Notes

You can try Contextuum at www.contextuum.ai

Amie and Contextuum will be featured at the Long-Term Strategy Conference 2026. This year’s theme is AI in Strategy Creation | Beyond Trendslop – https://strategyconf.fwconsulting.com

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

Ep 38 – The Bellhop and the Sardines w/Amie Devero

Your company knows that it needs to move quickly once a corporate strategy has been developed, to get the document in the hands of the staff.

But what does it mean to “get it into their hands?” Send them a pdf? Get them to watch a video? Attend a town hall? Attend a briefing from their manager, after she has received her briefing?

This is a massive problem and here today to apply an AI-driven solution is Amie Devero. Tune into this episode to hear from us as we tackle the issue of strategy activation together.

Show Notes

You can try Contextuum at www.contextuum.ai

Amie and Contextuum will be featured at the Long-Term Strategy Conference 2026. This year’s theme is AI in Strategy Creation | Beyond Trendslop – https://strategyconf.fwconsulting.com

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

Ep 37 Why Global Conflict Has Your C-Suite Knee-Jerking Strategy Once Again

Your company prides itself on its long-term thinking, planning and acting. But now that times are difficult due to the outbreak of a war, you are wary of what might happen given your experience of COVID, supply chain breakdowns and sudden tariffs.

During these extreme events, you saw C-Suite executives delve into the weeds, doing the work of managers. As their time horizons shortened, they ignored the big picture until well after the crisis passed. This meant lost opportunities, and a lack of preparation for future threats.

How should you intervene given that it appears as if the roots of long-term thinking are weaker and shallower than you thought?

In this episode we look at your leadership system and where it lacks disciplined practices for long-term focus.

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

Ep 37 Why Global Conflict Has Your C-Suite Knee-Jerking Strategy Once Again

Your company prides itself on its long-term thinking, planning and acting. But now that times are difficult due to the outbreak of a war, you are wary of what might happen given your experience of COVID, supply chain breakdowns and sudden tariffs.

During these extreme events, you saw C-Suite executives delve into the weeds, doing the work of managers. As their time horizons shortened, they ignored the big picture until well after the crisis passed. This meant lost opportunities, and a lack of preparation for future threats.

How should you intervene given that it appears as if the roots of long-term thinking are weaker and shallower than you thought?

In this episode we look at your leadership system and where it lacks disciplined practices for long-term focus.

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

The One Diagnostic Step Every Failed AI Rollout Skipped

There are two ways a board loses confidence in a CEO’s AI strategy. One is watching a rushed rollout blow up in public. The other is watching nothing happen, quarter after quarter, while rivals pull ahead. Leaders treat these as opposite sins — one of recklessness, one of paralysis. They are the same sin wearing two costumes.

Consider a government vehicle-inspection office. For years, getting a car certified meant a wasted morning: unexplained queues, arbitrary waits, a process nobody could explain and everybody dreaded. The clerks weren’t the problem. They were as trapped in the system as the drivers standing in line.

When the office was finally redesigned, the fix didn’t come from the counter staff working harder. It came from above — from leadership finally treating the process itself as something to be mapped, tested, and rebuilt. Decades of avoidable frustration turned out to be a leadership failure wearing a service-counter disguise.

That’s the pattern behind almost every stalled or embarrassing AI rollout today: cause and effect get separated. The department that visibly breaks is rarely the one that made the mistake. The quarter where the failure shows up is rarely the quarter where it was made. That lag is exactly why the rushed CEO and the frozen CEO can’t see they share a cause. Skip the diagnosis, and the bill arrives later — as a scrapped pilot, a quiet rollback, or a board that’s run out of patience. Each time, it looks like an isolated, unrelated event. It isn’t.

The Proof Is Piling Up

This isn’t a resource problem, and it isn’t confined to one company, sector, or country.

Starbucks spent nine months running an AI tool meant to automate beverage-inventory counts across its North American stores, before quietly retiring it after the system kept miscounting and mislabeling items, such as confusing similar milk types. Ford has been rehiring and promoting more than 350 experienced engineers after automated quality-control systems failed to capture the expertise of veteran employees. Commonwealth Bank of Australia replaced dozens of customer-service staff with an AI voice bot, then had to reverse the job cuts when the system couldn’t keep up and call volumes climbed. IBM automated large parts of its HR function, discovered the tool could resolve routine requests but stumbled on anything requiring judgment, and announced plans to triple its U.S. entry-level hiring soon after. A widely cited MIT study found that 95% of enterprise generative AI pilots fail to deliver measurable returns.

None of these were companies short on capital, talent, or enthusiasm. Every one of them had the AI capability. What none of them had was a diagnosis of the underlying process before the tool was chosen.

What Got Lost

That’s understandable, in a way. Most companies today are wide open to AI because their own stakeholders are demanding they keep up. A new tool appears, it gets deployed, and results get measured afterward. That works fine when the change is as simple as installing a new printer. It fails the moment the process underneath is genuinely complex — which is most of the time. What’s missing is the step where the existing process gets mapped, stress-tested for bottlenecks, and redesigned before automation is even on the table.

Both the rushed CEO and the frozen CEO would benefit from the identical corrective move — not “go faster,” not “go slower,” but insert the diagnostic step neither is in the habit of taking.

If that sounds obvious, it’s worth asking why so many organizations quietly abandoned it. Process management — mapping, testing, and redesigning core operations — was standard executive discipline in the 1990s, built on Total Quality Management, Lean, and the Theory of Constraints. Somewhere along the way, leadership teams let it lapse. The lesson hasn’t gone anywhere; it’s just been sitting unused. Years before generative AI, executives attempting Robotic Process Automation without first doing this work were warned by experts that skipping it was a recipe for failure. The warning was accurate then. It’s still accurate now, just louder.

There’s a second reason the step feels skippable: nearly every executive has personally felt AI work well. Ask ChatGPT or Claude a question on your phone, and an articulate, confident answer arrives in seconds. That experience quietly convinces leaders that AI should transform every part of the business with the same ease. But personal productivity gains and enterprise-wide transformation are not the same category of problem. Real organizational change requires the unglamorous work of scoping, staffing, and sequencing multi-year projects. There is no shortcut from a good chatbot answer to a redesigned supply chain.

One Reveal Worth Adding

In other podcast I have drawn a sharp line between planning and strategy: planning extrapolates from what you’re already doing, while strategy forces a real choice that involves tradeoffs. Most AI “strategies” are actually AI plans — lists of tools to deploy, extrapolated from what competitors are doing, with no binding constraint identified and no real choice made. A genuine AI strategy starts by asking which single process constraint, if resolved, would unlock the most value — and works backward from there. Everything else is activity dressed up as strategy.

The Actual Fix

The CEOs who rush and the CEOs who freeze are both missing the same discipline — not courage, not caution, but the willingness to slow down at the exact moment everyone else is speeding up. The rushed CEO skips the diagnosis to look decisive. The frozen CEO avoids it to look careful. Neither has done the work.

The fix isn’t a faster rollout or a longer pause. It’s a process that’s been mapped and stress-tested before a single tool gets chosen. Boards don’t ultimately reward the leader who moved first or the one who moved last. They reward the one who knew where to look before moving at all.


PS: 5 Prompts to Use With Your Favorite LLM

Copy these into Claude, ChatGPT, or your assistant of choice to apply the article to your own organization.

  1. Find your lag. “Walk me through a recent failure or slowdown in my organization. Help me trace it backward — what department, decision, or process choice from 12–24 months ago might actually be the root cause, even if it doesn’t look connected on the surface?”
  2. Spot your substitute behavior. “I’m about to approve/reject an AI tool for [describe the process]. Before I decide, ask me questions that test whether I’ve actually mapped this process and identified its bottleneck — or whether I’m just reacting to pressure to ‘do something.’”
  3. Run a mini process diagnosis. “Here’s how [a specific process] works today, step by step: [describe it]. Identify the most likely bottleneck, and tell me what would need to be true for automating this process to actually help rather than just move the bottleneck somewhere else.”
  4. Test for real strategy vs. planning. “Here’s my current AI roadmap: [paste it]. Using Roger Martin’s distinction between planning and strategy, tell me honestly whether this is a strategy — with a real choice and a clear binding constraint — or a plan that’s just a list of tools.”
  5. Pressure-test your own excuse. “I’m the CEO/leader in this situation: [describe whether you’re moving fast or holding back on AI]. Play devil’s advocate and challenge me on whether my current pace is actually a disguised way of avoiding a proper process diagnosis.”

The Missing Run: Why Your Innovation Efforts Remain Uninspiring and Empty

As the person responsible for driving innovation in your organisation, you have probably sat through a version of this conversation more than once.

The leadership team agrees that a new category is needed. Everyone nods. A workshop is scheduled. Consultants are hired, sticky notes are deployed, and three months later the team resurfaces with a list of incremental improvements dressed up in the language of transformation. Nothing changes. The cycle repeats.

This is not a talent problem. It is not a budget problem. It is not even a creativity problem — though it will feel like one. It is a navigation problem. And the reason it keeps recurring is that most organisations begin every innovation effort from the same invisible assumption: that they already know what kind of thing they are trying to become. They don’t. And without that clarity, no workshop, no consultant, and no off-site retreat will produce a genuinely new category. You will keep generating better versions of what you already are.

There is a framework that changes this calculus entirely. It arrived quietly, in a new book by Joe Pine — the same strategist who gave executives The Experience Economy twenty-five years ago and reshaped the way the world thought about what companies actually sell.

What a Category Actually Is

Before you can design a new category, you need a precise definition of what a category is. In business, a category is not a filing label or a market segment. It is a space in people’s minds — the mental frame that allows a customer to understand what a product is, where it belongs in their life, and why it matters. “Smartphone,” “microwave oven,” and “streaming service” are all categories that someone invented. Each one began as an answer to a need that customers had not yet been able to name.

Category design — the deliberate act of creating a new mental frame rather than competing inside an existing one — is widely discussed and rarely achieved. Most executives who attempt it eventually conclude that it requires a creative leap they cannot engineer. That conclusion, it turns out, is wrong. What it actually requires is a ladder.

The Ladder Most Executives Have Only Seen Half Of

Pine’s original insight, from The Experience Economy, was that organisations don’t just sell things — they offer value at different levels, and those levels form a hierarchy. At the bottom are commodities: undifferentiated raw inputs where price is everything. Above that are products: manufactured goods with consistent specifications. Above that are services: activities performed on behalf of the customer. And above that are experiences: carefully staged events that engage customers emotionally and memorably.

Every hotel in the world, for example, offers a blend of products and services — a room, a meal, a concierge. A smaller number have moved up to experiences: the Marriott’s flagship properties with their signature design and curated atmosphere. Sandals, in the Caribbean, built an entire brand around the all-inclusive experience category. Each of these companies moved up Pine’s ladder deliberately, and each time they did, they left their competitors arguing about price on the rung below.

Here is what Pine’s original framework did not include — and what his new book, Transformation Economy, now adds. There is a fifth rung. Above experience sits transformation: an offering that does not merely engage or delight the customer, but permanently changes them. Not their situation. Not their environment. Them — their skills, their identity, their capabilities, their trajectory.

This rung exists in every industry. In most, it is unnamed, unclaimed, and therefore available. It is the most defensible category a company can occupy, and the hardest to copy, because transformation is not a feature. It is a relationship with a long-term outcome.

Rung Invisibility: The Hidden Reason Innovation Stalls

Most companies have never asked which rung they currently occupy. They operate without a precise definition of their own offering type, which means that when they sit down to innovate, they have no fixed starting point. Call it rung invisibility: you cannot climb toward a destination you cannot see.

This is the innovator’s dilemma in its most structural form. It is not that successful companies refuse to innovate — it is that they keep innovating on the wrong rung. They add features to products, extend services, improve experiences, and call it transformation. The ladder makes the distinction visible. Once you can see the rungs, you can locate yourself accurately, name the next rung, and build toward it with precision.

Waiting With a Destination in View

In 2007, Andrew Ng began uploading his Stanford computer science lectures to the internet. The vision was clear: university-quality education, accessible to anyone, anywhere, free. What was not yet ready was the road. Broadband penetration was uneven. Streaming infrastructure was immature. Mobile adoption had not reached the scale required. The concept of learning via video had not yet been normalised for a mass audience.

Ng spent five years building precursors, testing formats, and watching the infrastructure mature. When Coursera launched in 2012, it was not because the idea had finally arrived — it was because the enabling conditions had. MasterClass followed a similar logic: the transformation offering was clear (learn directly from the world’s best practitioners, not just their subject matter), but the model required cinematic production quality and broadband capable of delivering it at scale. Both companies launched not when they were ready, but when the world was.

This is a categorically different posture from running innovation workshops. It is not luck. It is not serendipity. It is the discipline of naming a destination — a specific rung, a specific transformation offering — and then building the long-term strategy around the conditions that will make the climb viable. Pine himself waited over twenty-five years to write Transformation Economy. As he has said, the world simply wasn’t ready before now.

Corporate Inspiration at Its Finest

As a leader, you have probably tried to inspire your organisation through personal energy — motivating speeches, bold vision statements, off-site retreats designed to generate momentum. When the results are mixed, the temptation is to conclude that you need more charisma, a better facilitator, or a more compelling narrative. You don’t. What you need is a structure that does the inspiring for you.

This is what Pine’s ladder offers when it is embedded in a corporate strategy: inspiration that lives in the architecture of the plan itself. Aspirational but credible. Fact-based. Free of hyperbole. Specific enough to span a decade without losing its force. When employees understand not just what the company does today but which rung it is climbing toward — and what conditions the organisation is watching for — they engage differently. The destination gives their work a direction that no workshop can manufacture.

Steve Jobs was explicit, in at least one public interview, that Apple’s strategy was to wait — to define the destination clearly and hold it until the technology matured enough to make the climb possible. Inside Apple, the roadmap to the iPhone and iCloud gave those who knew it something to work toward that transcended any individual product cycle. That kind of inspiration is structural, not charismatic. It is replicable. And it begins with locating yourself honestly on the ladder.

What to Do Next

Every organisation, without exception, can do this. The transformation rung exists in your industry. It is almost certainly unnamed. The fact that it is unclaimed is not a warning — it is an invitation.

The work begins with three questions. What rung does your organisation currently occupy — precisely, not aspirationally? What would a transformation offering look like in your sector: what would it permanently change about your customer? And what enabling conditions — technological, cultural, regulatory, infrastructural — are not yet mature, but are on their way?

The EndPoint Method offers one systematic approach to answering these questions within a long-term strategy process. But the starting point is available to any leadership team willing to look at the ladder honestly and ask where they are.

Innovation is not a creativity problem. It is a navigation problem. Pine’s ladder is the instrument. The fifth rung is waiting.

PS — Five Prompts to Take This Further

Use these with any AI assistant (Claude, ChatGPT, or similar). Replace the bracketed text with your own details.

Prompt 1 — Locate your rung “I work in [industry]. Our core offering is [brief description]. Using Joe Pine’s five-rung ladder — commodities, products, services, experiences, transformations — help me identify which rung we currently occupy and what evidence supports that assessment. Be precise, not flattering.”

Prompt 2 — Define the transformation offering “In the [industry] sector, what would a genuine transformation offering look like? Define it using Pine’s standard: an offering that permanently changes the customer themselves, not merely their situation or experience. Give me three specific examples of what this could mean for a company like [company type].”

Prompt 3 — Map the enabling conditions “The transformation offering I want to build is [brief description]. What external conditions — technological, cultural, regulatory, or infrastructural — are not yet mature enough to support this at scale? Which of these are likely to mature in the next five to fifteen years, and what signals should I be watching for?”

Prompt 4 — Diagnose your innovation process “My organisation runs [describe your current innovation process — workshops, sprints, planning cycles]. Using the concept of rung invisibility — the idea that companies cannot innovate toward a destination they cannot see — identify the specific points in our process where the absence of a named transformation rung is likely to be causing us to recycle existing assumptions.”

Prompt 5 — Draft the strategic narrative “Help me write a one-page internal strategic narrative for my leadership team that: names our current rung on Pine’s ladder, defines the transformation offering we are building toward, identifies the two or three enabling conditions we are watching, and explains why this is a navigation strategy rather than a creativity exercise. Tone: direct, credible, free of consultant language.”

P.S. The LTSP26 Conference is open for registration here on Linkedin. https://www.linkedin.com/events/7475287796359028737?viewAsMember=true. Part of the lineup will feature Category Cathy, an interactive AI persona with unique knowledge of work by experts like Joe Pine, author of Transformation Economy.

The CEO Who Solved Everything and Inspired No-one

You are putting in serious effort to motivate your team — and it still isn’t working. The hours are long, the intent is genuine, and the results are stubbornly flat. Before you blame your communication strategy, your budget, or your personality, consider a different diagnosis entirely.

Two fictional CEOs illustrate the problem.

Marcus is a decisive firefighter. He earned his position by tackling the problems nobody else would touch, and he has been doing the same thing ever since. Elena takes a more consultative path. She commissions engagement surveys, listens carefully to what staff say, and builds action plans from the results.

Yet both are looking at the same uncomfortable numbers: absenteeism climbing, burnout reports rising, and employees quietly asking each other, “Where exactly are we headed?” Both assume the problem is in the delivery — the messaging, the resources, the rollout. They are looking in the wrong place.

The actual diagnosis is a pattern called “Follower-Friendly Failure.”

The Same Mistake in Different Clothes

Follower-Friendly Failure is the attempt to build organisational momentum by removing friction. Fix the complaints. Address the survey results. Solve the urgent problems. The instinct is generous — leaders genuinely want to make things better for their people — but the strategy is structurally flawed.

Marcus and Elena look like opposites: urgent problem-solver versus consensus-builder. But they are making the same error in different packaging. Their failure is not in how they lead. It is in what they are leading toward — or rather, the absence of any clear answer to that question.

Elena’s approach is particularly instructive. Aggregating staff concerns produces a politically safe wish list, not a strategy. It assumes that resolving individual frustrations will compound into collective motivation. It won’t. Addressing one round of complaints simply surfaces the next round. The circle is vicious, and staff eventually exhaust themselves chasing problems that regenerate faster than they are solved.

The missing ingredient is not smarter problem-solving. It is a destination.

In this context, a destination is not a goal, a value, or a problem to be solved. It is a specific, vivid picture of where the organisation will stand at a defined point in the future — real enough that an ordinary person can orient themselves toward it.

What Political Science Reveals About Leadership

Research on voter behaviour offers an unexpected window into how destination-clarity functions as a loyalty mechanism. Studies of Donald Trump’s coalition have consistently found that roughly 25–35% of his supporters privately dislike specific policies, find aspects of his persona difficult, and disagree with particular decisions. They back him anyway.

The reason is not charisma, party loyalty, or agreement with the plan. It is agreement with the destination. These voters know where he says the country is going, and that clarity holds them even when the specific steps, or personal foibles do not.

The organisational parallel is direct. Every leadership group contains a subset of destination-first followers — people who will tolerate management friction, imperfect policies, and even a leader they find personally disagreeable, provided they can see clearly where the organisation is headed. Marcus and Elena have no mechanism for reaching this group because neither has named a destination unambiguous enough to reach them.

This is what Dr. Riel Miller, a UNESCO senior adviser, calls Futures Literacy: the capacity to use the future as a resource for acting in the present. It requires holding the future genuinely open — treating several possible destinations as real — until a single, unambiguous endpoint is chosen. Once that commitment is made, something shifts. Inspiration and discretionary effort are not manufactured through communication techniques. They are released.

This distinction matters more than most leadership development programmes acknowledge. Charisma, communication skill, and policy competence are all useful. But none of them substitute for a destination that employees can inhabit in their imagination before they inhabit it in reality

The Leading Indicator No Dashboard Captures

Executives searching for evidence that a strategy is working typically reach for lagging indicators: engagement scores, C-suite alignment, project milestones, revenue shifts. These confirm what has already happened. They do not tell you whether the organisation is actually moving.

There is a better signal, and it costs nothing to detect.

Consider an employee — call her Jody — who works in a mid-level, non-senior role. Her department has been identified as high-leverage: it sits in the 20% of organisational effort that drives 80% of strategic results, directly connected to a 15-year destination the company has committed to.

Without a clear destination, that leverage is invisible to Jody. She spends Monday doing what she did the Monday before. This is not apathy. It is a rational response to ambiguity. When no clear endpoint exists, the safest professional behaviour is to replicate what worked yesterday. Jody is not the problem. The missing destination is.

With one — a specific, unambiguous endpoint she can picture and act toward — something different happens. On Monday morning, unprompted by her manager, she spends three hours doing something she has never done before: taking deliberate actions aligned with where the organisation says it is going. Not because she was told to. Because she can see the destination and has decided to move toward it.

Notice what did not cause this shift: not a town hall, not a revised KPI framework, not a team-building exercise. The destination did the work. Her manager’s job, once the destination is clear, is largely to stay out of the way.

That behaviour — one ordinary person in a non-senior role doing something genuinely novel in alignment with the stated direction — is the leading indicator that a strategy is alive. Engagement surveys can score well while this signal is completely absent. The signal’s presence means the destination has landed. Its absence means it has not, regardless of what the dashboard reads.

When enough Jodys emerge across an organisation, the needle moves. Not because leadership pushed harder, communicated more cleverly, or solved one more urgent problem. But because ordinary people with real jobs decided, on their own initiative, that the destination was worth moving toward.

The practical implication is uncomfortable for leaders trained in comprehensive planning: resist the pressure to make the destination inclusive. A destination designed not to alienate anyone ends up directing no one. Choose one. Make it unambiguous. Then watch what Jody does on Monday morning.

Five Prompts for Deeper Reflection

Use these with any AI assistant (or as journaling prompts) to apply the ideas in this article to your own leadership context.

Prompt 1 — Diagnose your own Follower-Friendly Failure

“Here is how I currently try to motivate my team: [describe your approach]. Based on the distinction between problem-fixing and destination-setting, identify where my current approach might be producing Follower-Friendly Failure. What am I likely missing, and what would a clearer destination look like in my specific context?”

Prompt 2 — Test your destination for ambiguity

“Here is our current strategic vision or mission statement: [paste it]. Assess whether this constitutes a genuine, unambiguous destination that an ordinary employee could act toward on Monday morning — or whether it is a wish list, a values statement, or a problem-solving agenda in disguise. Then suggest what a sharper destination might say instead.”

Prompt 3 — Find your Jody

“Our organisation has articulated the following strategic direction: [describe it]. Help me identify what a ‘Jody Bloggs’ signal would look like in our context — that is, what specific, observable, novel behaviour by a non-senior employee would indicate that our destination has genuinely landed, rather than merely been communicated.”

Prompt 4 — Identify your destination-first followers

“The article describes a subset of followers who are loyal to a destination rather than to a leader’s personality or specific policies. Thinking about my own team or organisation, help me profile what this group might look like: how would I identify them, what do they need from a destination to engage, and how might I be inadvertently failing to reach them with my current communication?”

Prompt 5 — Rewrite your strategy communication through a Futures Literacy lens

“Here is how I typically communicate our strategy to staff: [paste an example — a town hall script, an all-staff email, a strategic summary]. Rewrite this using Futures Literacy principles: remove problem-solving language, eliminate wishlist elements, and replace them with a single unambiguous destination that an ordinary employee could picture and act toward. Show me the before and after side by side.”