Today, your executive team fills SWOT boxes in 90 minutes and calls it strategy.
Tomorrow’s competitive landscape will punish that superficiality mercilessly. Chris Fox predicts the emerging standard: double-barreled insight generation that combines intellectual analysis with visceral pattern recognition.
The companies that master this before 2027 will spot their Kodak moments early enough to pivot. The rest will wonder why their strategy sessions produced such weak insights while competitors transformed entire business models. This conversation reveals the magnitude gap that will separate strategic survivors from casualties.
Tune in to hear from me and my special guest, Chris Fox, as we tackle and try to solve this wicked problem together. We’ll be putting our heads together to find new ways of discussing strengths, weaknesses opportunities and threats – SWOT – that go beyond the usual thinking.
I’m Francis Wade and welcome to the JumpLeap Long-Term Strategy Podcast
Chris Fox is a strategy consultant and founder of StratNav, the collaborative platform for business strategy development and execution. With over 26 years’ experience, Chris helps leaders replace guesswork with evidence and execution. He also runs Chris C Fox Consulting, advising C‑suite teams on strategy that delivers
In the early 1980s, McKinsey told my employer at the time, AT&T, that the global market for mobile phones would top out at roughly 900,000 subscribers by 2000.
The actual number was 100 million.
A decade later, AT&T paid $11.5 billion for McCaw Cellular to claw its way back into the market it had walked away from.
Hundreds of America’s brightest minds had read the same report, nodded at the same conclusion, and missed by two orders of magnitude. The forecast was polished, confident, and built entirely on data from the past. It was, in today’s vocabulary, trendslop — and it predated AI by half a century.
If you sit at the top of a company anywhere in the world, you are now being asked to make similar bets with a tool that produces trendslop on demand. A recent Harvard Business Review article, “Researchers Asked LLMs for Strategic Advice. They Got ‘Trendslop’ in Return”, called out the pattern directly. Ask a large language model for strategic advice and you get confident, polished output that sounds insightful — until you look closely and realise it could have been written by a competent intern in an afternoon.
The good news: your instincts about AI are right. It can sharpen your strategy work. It can also wreck it.
The bad news: no settled playbook yet tells you which is which.
The Iron Rule You Already Know
As a young internal consultant at AT&T, I learned a discipline that has aged better than most of the company’s 1990s forecasts: Don’t automate what you haven’t baselined.
The same idea runs through every quality programme Toyota exported to factory floors around the world. Before you mechanise a process, you map it. You measure it. You understand its variation. Only then do you bring in the machine.
The current rush to “put AI into strategy” ignores this rule. Most executive teams cannot describe how their own strategy actually gets made. Strategy creation happens once every two or three years. It rarely gets documented. Institutional memory leaks out with every senior departure. No baseline exists.
Then the LLM is invited in. And it produces — predictably — trendslop.
The problem isn’t the AI. The problem is that the iron rule was broken before the model was ever prompted.
Where AI Helps, Where It Harms
The EndPoint Method I use breaks strategy work into six stages: build a Snapshot of where you are today; pick a Target Year fifteen to thirty years out; generate Scenarios for that future; pick one scenario and translate it into numbers; Backcast milestones from that endpoint to the present; and only then build a Short-Term Strategy Map for the first two years.
Across more than sixty engagements, I have watched AI’s effect on each stage. The pattern is now clear.
AI is a net positive in exactly one stage: the Snapshot. Here, the work is synthesis — pulling together what is already known about your organisation, your market, and your competitive position. The LLM reads documents fast, finds patterns across them, and surfaces contradictions in your own data that the room had stopped seeing. It augments without replacing.
AI is destructive in two stages, and they happen to be the most consequential: Picking a Target Year, and Picking-and-Translating a Single Scenario into Numbers.
These are the moments of commitment. They demand differentiation — a stance that sets your firm apart from the average. An LLM, by design, gives you the average. It will hand you a target year that mirrors what every other company in your sector has chosen. It will quantify your scenario the way every scenario in its training data has been quantified. Use it here and you sleepwalk into the same future as your competitors.
The remaining three stages — Generating Scenarios, Backcasting, and Short-Term Strategy Mapping — are mixed. AI helps when used as a sparring partner. It harms when used as a decision-maker.
The Fix
Over the past year, my team has run strategic planning retreats with AI integrated at chosen moments and in a deliberate way — never as the source of commitment.
The pattern that works is consistent. The group defines the issue and its causes manually first — sometimes a recent trend, sometimes a decade-long problem. Only then is the LLM brought in, with a sharp prompt. For example: “Given the persona we have just described and the specific belief they hold, what three scenarios could shift their attitude?”
Within seconds, the group absorbs the conventional wisdom and moves past it. The LLM expands ideas, synthesises inputs, and surfaces blind spots the room could not see on its own. It is never asked to commit, to judge, to prioritise, or to own a tradeoff.
Decompose your strategy work. Insert AI only where it adds value. Keep human commitment, judgement, and ownership intact.
What This Quarter Looks Like
The executives who win the AI moment in strategy will not be the ones who feed their hardest questions to an LLM and hope for the best. They will be the ones who honour AT&T’s iron rule and Toyota’s philosophy of automation: baseline first, then mechanise.
So here is the work in front of you this quarter.
Do not ask the LLM where to take your company. Ask it to help you see what you already have. Build the Snapshot. Map your strategy-making process for the first time. Document the institutional memory before it walks out the door.
Only then, and only at the stages where it adds value, bring AI into the room.
Your suspicion was right on both counts. AI can improve the process. AI can also do damage. Baseline first. Then, and only then, automate.
Five Prompts to Take This Further
1. Diagnose your current practice.“Describe how strategy actually gets made in our company today — who initiates it, what inputs feed it, how decisions get committed to, and where the process is undocumented. Then identify three places where we are currently asking AI to do work we have never baselined.”
2. Audit your strategy document for trendslop.“Here is our current strategy document [paste]. Identify every statement that could plausibly appear in any company’s strategy document in our industry. Highlight the language that is generic, average, or undifferentiated — and explain why each phrase fails to set us apart.”
3. Build a working Snapshot.“Read these three documents: last year’s plan, our most recent board minutes, and our latest competitor analysis [attach]. Surface every contradiction between them, every unexamined assumption, and every gap in evidence. Do not propose solutions — only surface what is already there.”
4. Sharpen a scenario with an opposing view.“We are considering [X scenario] as the future our strategy is built around. Argue against it. Give me the five strongest reasons a sceptical board member would push back on this scenario, and the historical analogies they might cite.”
5. Pressure-test your commitment.“Here is the single scenario we have chosen and the numbers we have attached to it [paste]. Identify the three commitments we are implicitly making that the rest of the document does not acknowledge. Where would this strategy break if our chosen Target Year arrived three years later than expected?”
P.S. The impact of AI on strategy creation is forcing its way into our thinking every day. You wish you could keep up, but so much is changing so quickly that it’s hard. The good news is that this is the theme of our September 15-17, 2026 strategy conference. Save the date in your calendar!
In this episode, we continue our discussion of the AI-Powered Professional by returning to the AI Researcher persona. Picking up from the prior conversation (episode 149) on information overload and information toxicity, Ray, Augusto, and Francis explore how AI can help professionals move from traditional search toward more collaborative research, synthesis, comparison, and knowledge discovery. They discuss deep research tools, source verification, using multiple AI systems to challenge each other, Google NotebookLM as a grounded research workspace, AI-assisted book reading and writing, proactive information discovery, and the importance of treating AI research outputs as drafts or hypotheses that still require human judgment.
(If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/150 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 Researcher: From Information Overload to Active Knowledge Synthesis (Part 2) 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 Researcher: From Information Overload to Active Knowledge Synthesis (Part 2)
Ray Sidney-Smith
Augusto Pinaud
Art Gelwicks
Francis Wade
Show Notes | The AI Researcher: From Information Overload to Active Knowledge Synthesis (Part 2)
Resources we mention, including links to them, will be provided here. Please listen to the episode for context.
ResearchGate
Google Search
Google Scholar
Academia.edu
ChatGPT
Claude
Google Gemini
DeepSeek
Google NotebookLM
Google Alerts
Feedly
Feedly Pro
Zapier
Evernote
Evernote AI
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 Pinault with Frances Wade and Art Gelwix.
Ray Sidney Smith | 00:19
Welcome back, everybody, to ProductivityCast, the weekly show about all things personal productivity. I'm Ray Sidney Smith.
Augusto Pinaud | 00:25
I am Augusto Pinaud.
Francis Wade | 00:26
And I'm Francis Wade.
Ray Sidney Smith | 00:28
Welcome, gentlemen, and welcome to our listeners to this continuation of our discussion on the AI-powered professional. In our last conversation, we were really defining the problem around information overload and many of the issues that the modern professional or knowledge worker really deals with as it relates to all of the information. In our lives today. And what we wanted to do in this episode is continue that conversation. And talk through really how to take the sometimes overwhelming amount of information, but the treasure trove of information that we have every day coming into our world and really utilizing it in productive ways. I think that today, Thanks to AI, we no longer need to think about the concept of a search engine. We need to really think about this from the perspective of it being a collaborative engine and there is this kind of reality that it could be considered an answer engine, a research engine, all of these kinds of ways in which we can coin it. There are lots of different use cases today. We're particularly focusing in on the research And these more sophisticated AI tools can now perform tasks previously reserved for a research assistant or for you to take intensive manual effort to produce. And so let's talk through some of the ways in which you're utilizing AI for research purposes. And let's think through perhaps some of the pitfalls that people fall into as they're trying to use AI for research.
Francis Wade | 02:12
I've been in a whole different world as a result of deep research in the last year. I remember before It was available. I used to do... Research via looking for documents like ResearchGate, I can search for a PDF using Google. I could search Google Scholar. You could go to academia.edu and What it would give back to me, these different sources, is Stuff that was close to what I was looking for, but not exactly what I was looking for. Matter of fact, it was often not close at all because I would have a specific question. And I'm trying to get a specific question answered. But I have to find somebody who actually answered that question in a document. Or maybe a book or in something. And usually I'd be looking for an academic source. And usually I wouldn't find anything.
So that's just, The game I would play was would be hunt and never find and that was 50%, 75% because I'd be looking for Esoteric stuff. Today, however, I have at my fingertips multiple A few different subscriptions to deep research and chat GPT does it for free up to a particular limit. And I can ask a very specific question. And to my shock, I can receive a plausible reply to my question Right. Pulls from credible sources for the most part. In the beginning, it When it first came out, they would pull from hallucinated sources, which was pain in the neck. But today... They've gotten to the point where They give credible... Specific answers to my very specific questions.
So my research has just multiplied by, it's hard to even compare what it was like No, Versal, what it was like before. Because I do so much of it now. It's really been a game changer.
So that's at the high level. The game is completely different for me right now. See you next year.
Ray Sidney Smith | 04:15
And it will be different in a year from now even. More so. As the technology gets better.
Francis Wade | 04:21
- I've told people that different parts of my work. Have undergone more change in the last year than in the last decade. 30 years before that, 20 years? And this is certainly one era that is completely different.
Augusto Pinaud | 04:37
Sometimes digging and research in a topic and sometimes more than the papers, find the books. What is the book that, okay, I read this book. Now, What other... Go. Into this line and with books go on the opposite line.
Sometimes it's not only The papers, it's the one to give a more... Book rented? What books? Hey, I'm dealing into... And sometimes once I want to deal or work or research into this particular idea, Bye. Where can I find those books? Because you think, okay, I want to get, how do you get granular and now fast? But then now how do you find those book, those authors, who are the authors who I'm researching this, the same areas that I'm research, it doesn't matter if they're agreeing or disagreeing with you, but how you find them, that was a labor Of love. A lot of times, to find those books and to find those authors.
And then after that, then you needed to start Figure out which one was good, which one was bad. That job? One from weeks to hours. And you in hours can get a list that is better than what I was able to produce in months. This gets very interesting, the issue. Who's this? The expectations that now the people have. Because for what you're describing, similar to mine, it's not only get the information, now that just you were able to get to the sources pass through. But the other part of the process is still, you need to still read it, still download them, still digest them, still trying to connect those dots. That is still takes the same amount of time, but then First part, it's fantastic. The issue I see with this is I find a lot of people who think that find the sources is enough. And find the sources is just a step one of X number of steps to be able to get to the next conclusion.
Ray Sidney Smith | 06:47
So I think about AI in a research context, when I say this is an AI researcher, Bye. That AI can still hallucinate. I know Francis is a little more, maybe more trusting than I am when it comes to these tools. But I've found ways to revalidate information even after it has pulled research And again, I Preface this always with everything I do with AI, I presume to be a first draft when it puts it out. And so I'm reviewing everything as though an intern handed it to me and it's an intern's work product.
So I need to make sure that it is correct. So we were all on the same page there. I think there are certain areas where AI is really good right now and where it will get better. I think that the deep research functions within all of the major tools that AI chat bots are pretty good right now.
So you have this deep research function in Claude Gemini, and ChatGPT. Personally, I've found that Gemini's does the best. I'm not sure why, but I just feel like it gets the most right when you prompt it correctly. And I don't like the verbosity around the deep research that Google puts out, but it's fine. It gets the data right, which is what I care about most. And that's one piece, which is you have this complex question and you need it to go out there and scour lots of sources and come back to you with an answer. And you don't know what the sources are. And I think in that sense, it can go ahead and find sources and then go ahead and do that analysis and synthesis that is really complex and therefore laborious and make it simpler.
Though Concern I always have with folks is that We're a little too trusting. So I'm going to, again, underscore the point that even after it does this research,...
In this episode, we continue our series on the AI-Powered Professional by introducing the AI Researcher persona. Ray, Augusto, and Francis discuss how AI is reshaping research, learning, and knowledge work by moving us beyond simple retrieval toward active knowledge synthesis. Along the way, they explore the problems of information overload, low-quality information, over-trusting AI-generated answers, news and social media overwhelm, and what Ray calls “information toxicity.” The ProductivityCast team also discusses practical ways to curate inbound information, reduce cognitive friction, use AI-generated briefs and drafts responsibly, and stay in control of your attention while working with smarter tools.
(If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/149 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 Researcher: From Information Overload to Active Knowledge Synthesis (Part 1) 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 Researcher: From Information Overload to Active Knowledge Synthesis (Part 1)
Ray Sidney-Smith
Augusto Pinaud
Art Gelwicks
Francis Wade
Show Notes | The AI Researcher: From Information Overload to Active Knowledge Synthesis (Part 1)
Resources we mention, including links to them, will be provided here. Please listen to the episode for context.
ResearchGate
Academia.edu
ChatGPT
Google Gemini
Google Workspace
Microsoft Copilot
Feedly
Evernote
Social Fixer
The New York Times
The Onion
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 Pinault with Francis Wade and Art Gelwick.
Ray Sidney Smith | 00:18
Welcome back, everybody, to Productivity Cast, the weekly show about all things personal productivity. I’m Ray Sidney Smith.
Francis Wade | 00:24
And I’m Francis Wade.
Ray Sidney Smith | 00:25
Welcome, gentlemen, and welcome to our listeners to this episode of ProductivityCast. This week, we are going to be continuing our dive into the world of artificial intelligence, which I like to call smart software, with another episode in our series of the AI-powered professionals.
So today we’re going to be focusing on research and what I’m coining here is the AI researcher persona and how these new tools are really transforming the process of learning and researching and knowledge work for us. We’re moving to a place where we can understand retrieval as basically active knowledge synthesis. And we’re going to be talking through some of the challenges that folks face with regard to information overload and otherwise.
So let’s first talk through the problems with research today. What do you find are the good or the positives around research today? And what are some of the problems that we experience? One of them we’re going to talk about, which is information overload. But there are others that are out there.
And then we can give that context. Color with regard to how we can use AI as a researcher to help us with that process or those problems.
So what do you feel like are the primary problems today with research.
Francis Wade | 01:47
I think in the past, very much a hit or miss kind of proposition. Where if you could find someone who had done the research… Answer the research questions that you have. You were extremely lucky. And the game was, how can I increase odds of success how can I be luckier So that meant that dwelling in places like Research Gate. Maybe at academia.edu.
Yeah. But ResearchGate was my goal, though. And For certain topics, especially the two that I specialize in, which are task management and strategic. Planning. I’ve pretty much got to the bottom of everything that I could find easily. It took a few years for each one, but I’ve sort of gotten to what I think is like the bottom. Where I read what they have to say. And I’ve noticed sort of where all the faults are why in neither field the research academics do is very useful in the real world?
You know, it’s very esoteric and it’s meaningful. Academics tend to write for each other. And for journals. And for advancement in their field. They don’t like to go into areas that are cross bouldery that I like to mix and match different fields. They don’t go interdisciplinary. It makes a real mess of the nice, clean, lines that they like to follow. And I don’t like to go into areas that, you know, If you become an expert in an area where there’s no conferences and no journals, no chairs and no departments anywhere in the world. If you go into an area like that, you know, you’re sort of dooming yourself to obsolescence.
So with those problems, It means that for the two areas that I’m interested in, there’s a, Not a lot of useful research. There is to find.
So finding something useful used to be a lucky proposition. And I would have to basically find someone who has enough experience in both areas to be able to do research in both areas so that they would have the questions. And finding that was like a needle in a haystack.
So it’s always been difficult in the two areas that I Try to find research written on. It’s always been an uphill struggle.
Augusto Pinaud | 04:02
I think it’s important to make an distinction between professional researching practices and the non-professional one. I agree in the professional researching the impact of AI has been incredible because now these people who Say. Knows better when they’re trying to search and look into information. Cinta was not available. When you go to the noun informal research. It’s interesting because I feel that we used to have Three levels of research, bad research, middle ground research, and good research. And now with the AI, we have gone and disappeared that middle because people think that they can find the answer that they believe is legit. Doesn’t matter if it’s true or it’s fake information or what it is. They can go bump into any of these agents. Get an answer. And because of that, people stopped digging. Into is this really legit? But when you think in the world of productivity, When the first book of David Allen came out, we were talking about 2001, It was hard to find the information. It was hard to find the principles behind unless you have access to them. 25 years later, you can find A ton of information. The question now is, How did you know that information is legit or not? And that’s why I think that middle ground has disappeared. You have the people who goes and do a prompt, and get an answer and assume Dad. The answer they’re getting is the truth. And because of that, that’s the stop of the research.
So what was part of the issues 20 years ago is, okay, I want to research this topic and now I have 20 books. No, they just go, ask two questions, get what they think is a truth answer, and take that That’s a fact. Then you have the other level that is the people who are going to get that and try to figure it out. Is this a fact? They’re going to try to dig out or it’s not a fact. And what is the fact? What is interesting for me with AI is That middle ground, that guy who will have get that fact and tried to see why. I don’t look legit or not legit. That disappeared. What I have seen is people getting the output that AI is giving them I’m taking them. It’s a truth. It’s an absolute truth that is even more scarier. And I have seen this In academic settings, I have seen this in professional settings, okay, where people go What is the obsolescence of this? Okay. Can you repeat that? I didn’t get an answer.
So when that is, they never really dig. Hold on, did you want to do the vendor? Did you, did the chat GPT was floating you know, That, I mean, how been… Wonderfully. Last week. My son is a baseball fan, so he was watching the baseball and he wanted to see the score, so he asked, Madame Eyre. And But I may say, the game has not started. It was time for the game to start. That’s true. The radio. Fuck. And you know, like, You’ve got me in the life. Damn, man. Give us whatever is for them. I’ve nothing to do. With the reality. And it was a great moment of, teach an opportunity because of that. If we will have the initial answer, what most people do, This other game has no authority. Okay, and you move on. But the reality is minimal. The game had started. We were in the middle of the game and there was a different score than what she was giving us on the third answer. And that is what Most people don’t notice when they go into this research. AI will give you an answer. The question is if that answer is actually the answer or.
Ray Sidney Smith | 08:11
Not. When it really matters, right? Learning that the game is not trivial, maybe not to your son, but to the rest of the world, you know, when it’s… I will.
Augusto Pinaud | 08:19
Make sure to tell him that right thing, that when the game is on, it’s not trivial. You are going down in that scale of people he likes. You’re going down, my friend.
Ray Sidney Smith | 08:27
The unfortunate part is if you say, hey, I just swallowed this thing mineral….
You’re in a strategy retreat. You see an opening to shift the conversation—a strategic insight you know could change the trajectory. You speak up with confidence. And then… blank looks. Awkward silence. The room moves on as if you hadn’t spoken.
It doesn’t matter if you’re the CEO, the board chair, or an ambitious director. The frustration is identical: you have strategic clarity, you know the frameworks, yet your interventions land with a thud while others command the room effortlessly. Most executives diagnose this as needing sharper frameworks or better presentation skills. Wrong problem.
This episode exposes what elite strategists do differently: they’ve built pattern libraries from accumulated case exposure that allow them to deploy diagnostic stories, pattern stories, and origin stories in the moment—not in PowerPoint decks afterward. You’ll discover why Julius Yego’s YouTube-driven Olympic medal validates cognitive science research on tacit knowledge, how Samuel Berger’s “intellectual dark matter” explains the gap between knowing frameworks and commanding strategic conversations, and why the three-season development model transforms in-the-room impact when executive programs don’t.
For global executives who’ve exhausted conventional development paths, this reveals the hidden capability that separates persuasive pattern recognition from forgettable framework recitation—and the deliberate practice method that builds it.
Enjoy the full video of this episode below for all subscribers.
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
In this episode, we continue our conversation on The AI Assistant as part of The AI-Powered Professional series. Picking up from Episode 147, the ProductivityCast team shifts from using AI merely to offload administrative friction and shadow work to thinking about AI as a true collaborative assistant. Ray, Augusto, and Francis discuss how to define roles for AI assistants, train them with useful context, manage multiple AI tools and personas, review AI-generated work as drafts, and build prompt workflows that help professionals get better results while staying firmly in control.
(If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/148 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 Assistant: Automating Administrative Friction and “Shadow Work”, Part 2 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 Assistant: Automating Administrative Friction and “Shadow Work”, Part 2
Ray Sidney-Smith
Augusto Pinaud
Francis Wade
Show Notes | The AI Assistant: Automating Administrative Friction and “Shadow Work”, Part 2
Resources we mention, including links to them, will be provided here. Please listen to the episode for context.
Microsoft Copilot
Google Gemini
Google NotebookLM
ChatGPT
Claude
Evernote
Zapier
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
[00:00:00] 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.
[00:00:18] Welcome back, everybody, to ProductivityCast, the weekly show about all things personal productivity. I'm Ray Sidney-Smith. Marco is jumping out. And I'm Francis Wade. Welcome, gentlemen, and welcome to our listeners to today's episode, where we're gonna continue our discussion on AI, and this is our series on the AI-powered professional.
[00:00:44] in our first episode, we started the discussion about the concept of utilizing generative AI. in this episode, we also started the process of talking about what an AI assistant is really [00:01:00] like, talking about some of those administrative frictions, being able to get rid of, and automate that out of, your world to some extent, and dealing with shadow work as well, defining shadow work and so on and so forth.
[00:01:13] We're gonna continue this topic into discussing today about really how to partner with your AI in a lot of ways, what the collaboration process really looks like. And so I'd like for us to discuss shifting using AI tools as a mechanism of just kind of offloading something, which it can do, but then becoming a more collaborative partner with that particular AI tool in order for it to become a true AI assistant.
[00:01:45] And so I'm thinking of things like how do we ensure that AI is taking over the right kind of work and that it's not taking over the work that we should be doing, and how do we maintain control and accuracy? And of [00:02:00] course, there are a bunch of boundaries and ethical considerations that we should be thinking about and some thoughts about the future.
[00:02:05] So let's start with what are some of those first principles, for us to be able to create a true collaboration partnership with our AI assistant?
[00:02:19] Sure. I'm thinking about this from the perspective that If I want to work with my AI assistant, I need to choose particular categories of work in which it can actually collaborate. So for example, I want it to be able to help me take a rough sketch that I've made on either my iPad or on paper, and then to have the AI turn that into a full-fledged drawing, a full-fledged cartoon perhaps.
[00:02:49] So the AI assistant is acting as my cartoonist, and so that's a role that I want the AI assistant to do. And while I can draw my [00:03:00] own cartoons, 'cause I've taken this drawing class, I feel competent to draw, you know, one part of a cartoon, but then it can fill in the rest by creating the other panels of the cartoon.
[00:03:13] And this is really helpful to me because now I can make the first drawing. It can be roughish, you know, to give it the idea of what I want, and now I can help it help me, quickly generate more panels and get the cartoon done by virtue of that. But the idea is that it's now a role that I want it to continually be helping me with, and so that is the cartoonist role.
[00:03:38] That's just one. I mean, like that, it doesn't, it doesn't have to be just role. It could be any number of things. But it's just like, that's the kind of thing that I'm thinking about. well, in the last episode, we sort of established the notion that, an AI assistant is like an intern who remembers everything, but doesn't have a whole lot of judgment.
[00:03:56] isn't, a really good judge of, you know, the [00:04:00] things, whatever it is that we happen to be expert at. It, it's too much to ask the AI to rise to our level of, insight and understanding. Having said that, there's a whole bunch of stuff that now looks to me that, it looks different to me because I can now see it as automatable.
[00:04:23] Like the example that you gave of, doing repetitive drawings or repetitive, animation. There's a bunch of things that I, and the list keeps growing, which is why I don't have a fixed answer. but it does start with this notion that I have an untrained intern that has infinite memory and infinite patience and doesn't have an attitude and works at all hours.
[00:04:48] And if I train that intern, then there's more and more things that the intern can do, and there's gonna be a new app tomorrow that- allows the intern to [00:05:00] do even more. So it's hard to say what specific role because the roles keep changing, and they keep being added to. if anything, I would say there's maybe a rule, which is that, try to give the intern as much as possible, but always be the person of last kind of decision.
[00:05:20] Be the one who's at the end checking to make sure the intern didn't make some, you know, gross error. So if there's any rule, that's the rule that I'm applying right now. Try to find more and more to give and then be the person at the end to do the checking. and then don't try to stress the intern out with judgment calls.
[00:05:42] and even the limit-- even the line on what I call a judgment call is changing with AI because it's getting better, You know, the AIs that I use, I use memory, so it understands me and what my judgment calls are, better and better each day. So it's a tough question to answer.[00:06:00]
[00:06:00] So just stepping up a level, I would say that just the concept of establishing roles for the AI is the first principle. It's not necessarily that you're going to ever be exhaustive in terms of creating the roles, because sometimes the role you need for a specific chat is defined in only that chat, and then there will be ones where you're gonna need that as an ongoing kind of recurring thing.
[00:06:29] It depends. You know, last episode I was talking about that wine help. You know, help me identify wine that I may enjoy based on my profile and educated that profile. But same thing on, on the professional side. I have a client who we, because of what they do, they, it's a report that is run every morning, and that report gets to them.
[00:06:53] And the problem is it's impossible to, to analyze it long enough. You know, you can see the report daily. You can maybe go a [00:07:00] couple days back. But human, it's hard to really create trends and things from that specific report. Where it's been very cool is a play on the role we create a chat for that neural network, okay?
[00:07:15] And now that report is dumped, for lack of a better word, into this chat. But this has now allowed us to identify trends not in three months, not in 90 days. Hey, this server last time this failed, okay, it was seven months ago. And it failed for three days. That information no human can provide for me. Okay?
[00:07:38] But allows you to start seeing that, and that make it very, very specific. Okay? Same thing, when you write. After you train, yeah, it required to train the intern, but after you train, say, "Okay, this sound like me. This doesn't sound like me." You know, one of the things that I love to do is when I get an [00:08:00] idea, okay, let me discuss this idea with the content of, okay, or the ideas or the understanding that AI has of X person.
[00:08:08] And you can say, "Hey, I want to look what will be the perspective of this text if Einstein read it." assuming you, you know what, physics and stuff. But that give you... Is the perspective you're going to get accurate? Well, it may be, it may not. But it will give you a counter that is very interesting.
[00:08:30] One thing that I do very often is find the arguments in favor and against this i- this concept, this idea that I'm working on. And it now get... You know, I think the definition, part of the definition or the issue is this, for a lot of people, is the first time they get access to an assistant, to an administrative assistant,
[00:08:53] For most people, that is a concept that they heard, that they, you know,...
There’s a number most government leaders would rather not think about. For Jamaica, it’s nine dollars.
That’s the country’s productivity measured as output per hour worked — US$9. Barbados, a neighboring island economy, produces more than twice that. Panama produces five times as much. Most strikingly, Jamaica’s hourly output is only marginally ahead of Haiti’s — a country that has experienced decades of political collapse and natural disaster.
The numbers are sobering. But they are not unique to Jamaica. Across the developing world, governments face a version of the same arithmetic: their economies are generating far less per hour of human effort than they should, the gap is wide, and it has been wide for decades.
What is less often discussed is the role that government itself plays in perpetuating that gap.
The Largest Economic Actor in the Room
In many developing economies, government directly produces somewhere between 15 and 20 percent of GDP through goods and services. That makes it the single largest economic actor in the country — larger than any company, sector or industry.
But its true influence extends much further. Government shapes the entire environment in which the other 80-plus percent of economic activity takes place, through four distinct levers: macroeconomic stability, institutional quality, infrastructure and public goods, and the signals and expectations it sends to investors, businesses and citizens about the future.
That fourth lever is the most underestimated. When a government is unpredictable, inconsistent or widely distrusted, it suppresses private investment and enterprise far beyond anything that shows up in its own budget. Conversely, a government that signals credible, long-term commitment to stability and growth creates a multiplier effect on every dollar the private sector deploys.
Jamaica has made genuine, internationally recognized progress on the first lever. Its fiscal turnaround since 2013 has been studied by other nations as a model of discipline. Debt ratios have fallen. Inflation has been tamed. And yet GDP growth has not followed at the pace the data might suggest it should. The reason is that macroeconomic stability, while necessary, is not sufficient. The other three levers matter just as much — and progress on those fronts is slower and harder to sustain across electoral cycles.
Why Elections Are the Wrong Unit of Time
The deeper problem is structural. Governments, by design, operate on four- or five-year cycles. The problems that most constrain developing economies — workforce quality, institutional trust, infrastructure, behavioral norms — compound over decades. They cannot be fixed within a single term. Often they cannot be fixed within a generation.
Take literacy. Jamaica’s literacy rate trails comparable peer countries by five or more percentage points — a gap that has been building since the 1960s. That gap is a direct and stubborn drag on workforce productivity. Closing it requires sustained investment and policy consistency across twenty or thirty years, not one budget cycle.
The same logic applies to institutional quality, infrastructure and public trust. These are slow variables. They respond to patient, consistent effort — not to whoever won the last election.
This is not pessimism. It is arithmetic.
The Countries That Played the Long Game
Two examples are instructive, and they have been cited often precisely because they are so striking.
Singapore in the early 1960s had a GDP per capita comparable to Jamaica’s. It was a small, resource-poor island with a mixed population, uncertain regional relationships and no obvious competitive advantages. Today it is among the wealthiest and most productive nations on earth.
Norway had oil. So did Nigeria, Angola, and Venezuela. The difference was that Norway resisted the temptation to spend its resource windfall immediately and instead built institutional structures — including a sovereign wealth fund now worth over a trillion dollars — designed to distribute wealth across generations rather than electoral cycles.
Both Norway and Singapore have populations of around five to six million — comparable in scale to many Caribbean and Central American nations. Scale was not destiny. What separated them was institutional patience: the willingness to make commitments that no single government could unilaterally reverse.
The Design Flaw in Most Development Plans
Many developing nations have tried long-term national development planning. The typical failure mode is nearly always the same: the plan belongs to one party. When the government changes, the plan either changes with it or quietly fades from view.
Jamaica’s Vision 2030 — an ambitious plan built around the aspiration to become “the place of choice to live, work, raise families and do business” — started with a bipartisan commitment, but has largely followed this pattern in recent years. It is rarely invoked by either major political party today. Its successes have not been studied. Its failures have not been honestly diagnosed.
Trinidad and Tobago offers a cautionary parallel. Multiple governments there have attempted national development plans under single-party mandates. Without cross-party commitment, each plan has been vulnerable to revision or abandonment when power changed hands. The structural challenges — growth, productivity, crime — remain largely unresolved.
The evidence from countries that have succeeded suggests a different architecture is required. Long-term national commitments need to be insulated from ordinary political interference — protected by cross-party agreement, legal frameworks and institutional norms in the same way that independent central banks or electoral commissions are protected. The goal is not to remove politics from policy. It is to place the most consequential long-horizon commitments beyond the reach of short-term political calculation.
This is not a utopian idea. It has been done — in countries that once looked very much like Jamaica does today.
The Immediate Return on Patient Thinking
There is a paradox worth naming. Patient, long-horizon thinking doesn’t only produce results over decades. It produces its first results immediately — in the minds of the leaders who adopt it.
The moment a government leader genuinely shifts from “what can I deliver before the next election?” to “what structural commitment can I make that a successor will be bound to honor?” — that shift is itself a form of progress. It changes which conversations happen, which trade-offs get made, which investments get prioritized. Institutional culture changes before the metrics do.
For any leader in the public sector who recognizes the structural arithmetic above, the question is not whether to think long. It is whether to do so quietly or loudly.
Either way, the calculus is the same. The countries that changed their trajectories did not do it in four years. They did it by making four-year decisions that pointed consistently in the same direction for forty.
Only the nations — and the institutions — willing to make and protect patient commitments have a realistic chance of closing the gaps that actually matter.
5 Prompts to Put These Ideas to Work
The arguments in this article become more useful when applied to your own institution. These prompts are designed for use with any AI assistant (Claude, ChatGPT, Gemini, etc.). Work through them in order — each builds on the last.
Prompt 1 — Reflect “I lead [describe your ministry, agency or department] in Jamaica. The article I just read argues that government influences GDP through four levers: macroeconomic stability, institutional quality, infrastructure and public goods, and public signals and expectations. Ask me a series of questions to help me identify which of these levers my organization influences most directly — and where the biggest performance gaps are.”
Prompt 2 — Reflect “Here is my organization’s current strategic plan: [paste it]. Review it against this standard: which commitments are genuinely structural — meaning they require ten or more years to fully realize — and which are short-term fixes unlikely to outlast the current administration? Then identify what is missing from the long-term column.”
Prompt 3 — Apply “Jamaica’s literacy gap has been building since the 1960s and is described as a ‘stubborn contributor’ to low productivity. Help me identify the equivalent stubborn contributors in my sector — the slow-moving structural gaps that no single government can fix alone. What data would I need to make this diagnosis rigorously, and what would a credible 20-year improvement trajectory look like?”
Prompt 4 — Create “Using Singapore and Norway as reference points — both small nations that made long-horizon institutional commitments that outlasted individual governments — help me draft a one-page strategic hypothesis for my organization. It should answer: what is the single most important structural commitment my institution could make today that would still be bearing fruit in 2040? Start by asking me three questions about my organization’s current situation.”
Prompt 5 — Master “The article argues that Jamaica’s Vision 2030 failed partly because it lacked cross-party commitment — and that durable long-term plans must be insulated from political interference the way electoral commissions are. Help me design a cross-party commitment framework for one specific policy priority in my sector. What institutional mechanisms would make it durable enough to survive a change of government? What would have to be true politically, legally and culturally for this to hold?”
P.S. The impact of AI on strategy creation is forcing its way into our thinking every day. You wish you could keep up, but so much is changing so quickly that it’s hard. The good news is that this is the theme of our September 15-17, 2026 strategy conference. Save the date in your calendar!
Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move.
But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass.
This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause.
The Real Problem Is Sequence, Not Ambition
CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void.
Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does.
Neither framing is quite right. In the end, CEO’s migrate towards short-term goals because they don’t have a reliable way to maintain both short-, mid-, and long-term momentum.
The deeper issue is that most organizations try to do too much in a single planning meeting.
Effective accomplishment of all three phases at the same time requires two distinct meetings, held weeks apart, each demanding a different posture from the leader. Getting the sequence right changes what the plan is, who owns it, and how fast it can move.
Clarifying Misconceptions About Long Horizons
Before the two meetings make sense, two widespread beliefs need to be addressed:
the first is that long-range planning is inherently vague, and therefore not worth taking seriously.
Mistake 1) This is a problem for CEOs who truly have big aspirations, because long-range planning calls for the decades needed to make breakthrough goals realistic and credible to stakeholders. Without adequate time, executives play the game mentioned before. They show up, nod, and wait for the pressure to disappear.
This view of long-range planning being vague is understandable but technically wrong.
The planning tools appropriate for year one of a strategy are genuinely different from those suited to year twenty-five — but that doesn’t mean the far end of the horizon is a guess. It just needs to be equipped in the right way.
For example, the Rolling Wave Technique leads to the use of different methods, mindsets and discussions for short- and long-term phases. It provides operational details in the short term, and higher-altitude targets and milestones in the long term.
Neither end is more rigorous than the other. They are rigorous in different ways. The confusion exists because precious few use the technique. It’s just not taught in most business schools as a component of corporate strategy.
Mistake 2) The second faulty belief is that long-term aspirations don’t matter. To explain why this is so wrong, consider a historical example.
Medieval cathedral builders routinely committed to projects spanning two to three centuries. No individual craftsman who broke ground would see the finished nave. Yet construction continued across generations, through plagues and political upheaval, because the aspiration was large enough to give the work meaning — and specific enough to give it credible direction. Floor plans existed. Proportions were specified. Progress was measurable even when the endpoint was a lifetime away.
This points to a counterintuitive truth: the grander the ambition, the more likely it is to unlock discretionary effort — the creativity and energy people typically reserve for pursuits they actually care about.
Modest, short-term goals produce compliance. In corporate life, these tend to be overwhelmingly financial.
Transformative goals, properly constructed, produce ownership. The audacity of a well-chosen endpoint is itself a management tool, one that most corporations never pick up.
With these misconceptions cleared up, here are the details of both meetings and how they are conducted.
Meeting One: The CEO Goes Quiet
The first meeting has one non-negotiable design principle: the CEO sponsors but does not lead. Or facilitate.
This is harder than it sounds. Most executives who have reached the top of an organization have done so partly through the force of their vision. They arrive at planning sessions having already formed views about where the company should go. The instinct is to share those views early — to inspire the team with a compelling picture of the future and let the session fill in the details.
Resist it. Completely.
The goals of this first meeting are for the executive team to construct the long-range aspiration themselves and define the means to accomplish it. That means choosing a target year — somewhere between fifteen and thirty years out — and then building the assumptions, scenarios, and numbers required to define what success looks like at that point.
It’s followed by the use of the Rolling Wave Technique to lay out a plan for the entire horizon, with more details in closer than later years.
Facilitators can guide the process. The CEO’s role is to hold the space while that process unfolds, tolerating the discomfort of an outcome they did not pre-select and cannot entirely predict.
What makes this worthwhile is what it produces: genuine co-ownership. Every figure the team debated, they will later defend. Every scenario they stress-tested, they trust because they built it. A strategic target and plan defined by the CEO and handed to the team is a document. A strategy the team constructed is a commitment — and the difference shows up in execution, not in the planning room.
For example, one team member assumes a technology shift in five years. Another assumes fifteen. Both assumptions are driving their instincts about investment and timing, silently, in every meeting they attend. Naming those beliefs, debating them, and converting them into dated claims is one of the most underrated outputs of a well-run long-range planning session. It also reveals where the team’s consensus is genuine and where it is merely polite.
Meeting Two: The CEO Becomes an Instigator
Several weeks after the first meeting — long enough for the plan to feel real, not so long that momentum fades — the CEO calls a second session. It has a single agenda item, framed as a question:
“Using the same logic we built together, how much faster could we realistically get there?”
The phrasing matters more than it might appear. This is not a demand for “twice the output in half the time” — the kind of arbitrary stretch target that produces creative accounting and quiet cynicism. It is an invitation to apply the team’s own reasoning to a compression problem. They set the destination and the pathway. Now they are being asked whether the chosen route is as efficient as it could be.
And because the team built the original logic, they are the only people positioned to answer the question credibly. They know which assumptions were conservative. They know where interdependencies between units create natural leverage — and where they create drag. They know which technologies on the industry’s horizon could compress a transition the plan assumed would take a decade. They know where the plan padded timelines because of organizational inertia rather than genuine constraint.
That collective intelligence almost never gets activated, because the question that unlocks it is almost never asked. Unfortunately, leaders tend to apply pressure before the team has built the logic, which means compression becomes a negotiation rather than an analysis. The two-meeting sequence reverses that order — and the difference in what the team produces is striking.
The best version of this second meeting doesn’t only produce a revised plan. It produces a set of credible acceleration options: specific conditions under which the timeline compresses, specific investments or decisions that could trigger those conditions, and an honest accounting of what would have to be true for the faster scenario to hold. The team leaves not just aligned, but strategically fluent in a way that one-off retreats almost never achieve.
Case in point: Before 2017, one of my clients in the Jamaican financial sector had never put a date to an assumption: “the average local customer is not ready for online services.”
When I challenged them to place a date on the moment when 50% of the population would reach that threshold, they predicted: 2028. They wove that date into their plan.
Three years later when the COVID-19 pandemic arrived, that plan was simply accelerated (i.e. compressed) to be implemented within months rather than a decade. They were lucky.
The Resilience Dividend
There is a benefit to this process that rarely appears in planning frameworks: the organization becomes significantly harder to surprise.
An executive team that has jointly built a long-range plan, surfaced its embedded assumptions, dated them, stress-tested scenarios, and explored acceleration options has essentially pre-thought a wide range of futures.
When the external environment forces their hand — a market disruption, a technology shift, a crisis that compresses years into months — they are not improvising. They are activating a version of something they already worked through. The decisions feel fast because they had already built the internal logic needed to respond.
This is not a theoretical benefit. Organizations routinely discover, under pressure, that their plans contained a faster path they simply hadn’t chosen to pursue yet. The companies best positioned to accelerate in a crisis are the ones that already knew, in principle, how acceleration was possible — because they had asked themselves exactly that question before one was forced on them.
The slow work of building shared logic, it turns out, is what makes rapid response possible. Resilience isn’t built in the crisis. It’s built in the room, in the meeting before the meeting, when the CEO is quiet enough to let the team think.
Why This Rarely Happens — and What to Do About It
The reason most aspirations which require long-term strategies end up stalling is that the people accountable for executing them never felt genuinely accountable for creating them. The CEO’s vision, however compelling, remains the CEO’s vision. Rollout becomes performance. Compliance replaces conviction. And when conditions change, there is no one in the room who feels responsible for updating the logic — because the logic was never theirs.
The two-meeting structure addresses this not through a motivational technique but through a structural one. Ownership is built in at the design stage. The compression question in the second meeting then activates that ownership, rather than challenging it.
The process asks something genuinely difficult of the CEO: to be quiet and patient at the moment when they most want to speak, and to ask a question — rather than issue an instruction — at the moment when they most want to apply pressure. Both moves feel counterintuitive. Both, consistently, work.
Begin with the meeting where you say less than you ever have before. What comes next will surprise you.
Use These LLM Prompts to Apply This Framework
Copy any of the following into an AI assistant to put the ideas in this article to work for your organization.
Pressure-test your current strategy “Here is our current strategic plan: [paste or summarize]. Using the Rolling Wave principle from the article I just read, identify where our plan conflates short-, mid-, and long-term planning into a single approach. What assumptions are we treating as facts? Which ones should have a specific date attached to them?”
Prepare for Meeting One “I am a CEO preparing to run a long-range planning session where my role is to facilitate, not lead. Our industry is [X]. Help me design a 3-hour agenda that guides my executive team to construct a 20-year aspiration themselves, without me imposing a conclusion. Include the questions I should ask — and the ones I should resist asking.”
Surface your team’s hidden assumptions “Here are the key assumptions embedded in our strategy: [list them]. For each one, challenge me to convert it from an open-ended belief into a dated, falsifiable claim. Then identify which assumptions, if wrong, would most significantly change our direction or timeline.”
Run the compression question “Here is a summary of our long-range plan: [paste summary]. Assume the logic is sound. Now help me identify: which parts of this plan are paced by genuine external constraints, and which are paced by internal inertia or conservative thinking? Where could the timeline realistically compress — and what would have to be true for that to happen?”
Build your resilience map “Based on the strategic plan below [paste], identify the three to five external disruptions — technology shifts, market changes, regulatory moves — most likely to force an acceleration of our timeline. For each, describe what an already-prepared organization would do in the first 90 days, versus one that had never considered the scenario.”
Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move.
But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass.
This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause.
The Real Problem Is Sequence, Not Ambition
CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void.
Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does.
Neither framing is quite right. In the end, CEO’s migrate towards short-term goals because they don’t have a reliable way to maintain both short-, mid-, and long-term momentum.
The deeper issue is that most organizations try to do too much in a single planning meeting.
Effective accomplishment of all three phases at the same time requires two distinct meetings, held weeks apart, each demanding a different posture from the leader. Getting the sequence right changes what the plan is, who owns it, and how fast it can move.
Clarifying Misconceptions About Long Horizons
Before the two meetings make sense, two widespread beliefs need to be addressed:
the first is that long-range planning is inherently vague, and therefore not worth taking seriously.
Mistake 1) This is a problem for CEOs who truly have big aspirations, because long-range planning calls for the decades needed to make breakthrough goals realistic and credible to stakeholders. Without adequate time, executives play the game mentioned before. They show up, nod, and wait for the pressure to disappear.
This view of long-range planning being vague is understandable but technically wrong.
The planning tools appropriate for year one of a strategy are genuinely different from those suited to year twenty-five — but that doesn’t mean the far end of the horizon is a guess. It just needs to be equipped in the right way.
For example, the Rolling Wave Technique leads to the use of different methods, mindsets and discussions for short- and long-term phases. It provides operational details in the short term, and higher-altitude targets and milestones in the long term.
Neither end is more rigorous than the other. They are rigorous in different ways. The confusion exists because precious few use the technique. It’s just not taught in most business schools as a component of corporate strategy.
Mistake 2) The second faulty belief is that long-term aspirations don’t matter. To explain why this is so wrong, consider a historical example.
Medieval cathedral builders routinely committed to projects spanning two to three centuries. No individual craftsman who broke ground would see the finished nave. Yet construction continued across generations, through plagues and political upheaval, because the aspiration was large enough to give the work meaning — and specific enough to give it credible direction. Floor plans existed. Proportions were specified. Progress was measurable even when the endpoint was a lifetime away.
This points to a counterintuitive truth: the grander the ambition, the more likely it is to unlock discretionary effort — the creativity and energy people typically reserve for pursuits they actually care about.
Modest, short-term goals produce compliance. In corporate life, these tend to be overwhelmingly financial.
Transformative goals, properly constructed, produce ownership. The audacity of a well-chosen endpoint is itself a management tool, one that most corporations never pick up.
With these misconceptions cleared up, here are the details of both meetings and how they are conducted.
Meeting One: The CEO Goes Quiet
The first meeting has one non-negotiable design principle: the CEO sponsors but does not lead. Or facilitate.
This is harder than it sounds. Most executives who have reached the top of an organization have done so partly through the force of their vision. They arrive at planning sessions having already formed views about where the company should go. The instinct is to share those views early — to inspire the team with a compelling picture of the future and let the session fill in the details.
Resist it. Completely.
The goals of this first meeting are for the executive team to construct the long-range aspiration themselves and define the means to accomplish it. That means choosing a target year — somewhere between fifteen and thirty years out — and then building the assumptions, scenarios, and numbers required to define what success looks like at that point.
It’s followed by the use of the Rolling Wave Technique to lay out a plan for the entire horizon, with more details in closer than later years.
Facilitators can guide the process. The CEO’s role is to hold the space while that process unfolds, tolerating the discomfort of an outcome they did not pre-select and cannot entirely predict.
What makes this worthwhile is what it produces: genuine co-ownership. Every figure the team debated, they will later defend. Every scenario they stress-tested, they trust because they built it. A strategic target and plan defined by the CEO and handed to the team is a document. A strategy the team constructed is a commitment — and the difference shows up in execution, not in the planning room.
For example, one team member assumes a technology shift in five years. Another assumes fifteen. Both assumptions are driving their instincts about investment and timing, silently, in every meeting they attend. Naming those beliefs, debating them, and converting them into dated claims is one of the most underrated outputs of a well-run long-range planning session. It also reveals where the team’s consensus is genuine and where it is merely polite.
Meeting Two: The CEO Becomes an Instigator
Several weeks after the first meeting — long enough for the plan to feel real, not so long that momentum fades — the CEO calls a second session. It has a single agenda item, framed as a question:
“Using the same logic we built together, how much faster could we realistically get there?”
The phrasing matters more than it might appear. This is not a demand for “twice the output in half the time” — the kind of arbitrary stretch target that produces creative accounting and quiet cynicism. It is an invitation to apply the team’s own reasoning to a compression problem. They set the destination and the pathway. Now they are being asked whether the chosen route is as efficient as it could be.
And because the team built the original logic, they are the only people positioned to answer the question credibly. They know which assumptions were conservative. They know where interdependencies between units create natural leverage — and where they create drag. They know which technologies on the industry’s horizon could compress a transition the plan assumed would take a decade. They know where the plan padded timelines because of organizational inertia rather than genuine constraint.
That collective intelligence almost never gets activated, because the question that unlocks it is almost never asked. Unfortunately, leaders tend to apply pressure before the team has built the logic, which means compression becomes a negotiation rather than an analysis. The two-meeting sequence reverses that order — and the difference in what the team produces is striking.
The best version of this second meeting doesn’t only produce a revised plan. It produces a set of credible acceleration options: specific conditions under which the timeline compresses, specific investments or decisions that could trigger those conditions, and an honest accounting of what would have to be true for the faster scenario to hold. The team leaves not just aligned, but strategically fluent in a way that one-off retreats almost never achieve.
Case in point: Before 2017, one of my clients in the Jamaican financial sector had never put a date to an assumption: “the average local customer is not ready for online services.”
When I challenged them to place a date on the moment when 50% of the population would reach that threshold, they predicted: 2028. They wove that date into their plan.
Three years later when the COVID-19 pandemic arrived, that plan was simply accelerated (i.e. compressed) to be implemented within months rather than a decade. They were lucky.
The Resilience Dividend
There is a benefit to this process that rarely appears in planning frameworks: the organization becomes significantly harder to surprise.
An executive team that has jointly built a long-range plan, surfaced its embedded assumptions, dated them, stress-tested scenarios, and explored acceleration options has essentially pre-thought a wide range of futures.
When the external environment forces their hand — a market disruption, a technology shift, a crisis that compresses years into months — they are not improvising. They are activating a version of something they already worked through. The decisions feel fast because they had already built the internal logic needed to respond.
This is not a theoretical benefit. Organizations routinely discover, under pressure, that their plans contained a faster path they simply hadn’t chosen to pursue yet. The companies best positioned to accelerate in a crisis are the ones that already knew, in principle, how acceleration was possible — because they had asked themselves exactly that question before one was forced on them.
The slow work of building shared logic, it turns out, is what makes rapid response possible. Resilience isn’t built in the crisis. It’s built in the room, in the meeting before the meeting, when the CEO is quiet enough to let the team think.
Why This Rarely Happens — and What to Do About It
The reason most aspirations which require long-term strategies end up stalling is that the people accountable for executing them never felt genuinely accountable for creating them. The CEO’s vision, however compelling, remains the CEO’s vision. Rollout becomes performance. Compliance replaces conviction. And when conditions change, there is no one in the room who feels responsible for updating the logic — because the logic was never theirs.
The two-meeting structure addresses this not through a motivational technique but through a structural one. Ownership is built in at the design stage. The compression question in the second meeting then activates that ownership, rather than challenging it.
The process asks something genuinely difficult of the CEO: to be quiet and patient at the moment when they most want to speak, and to ask a question — rather than issue an instruction — at the moment when they most want to apply pressure. Both moves feel counterintuitive. Both, consistently, work.
Begin with the meeting where you say less than you ever have before. What comes next will surprise you.
Use These LLM Prompts to Apply This Framework
Copy any of the following into an AI assistant to put the ideas in this article to work for your organization.
Pressure-test your current strategy “Here is our current strategic plan: [paste or summarize]. Using the Rolling Wave principle from the article I just read, identify where our plan conflates short-, mid-, and long-term planning into a single approach. What assumptions are we treating as facts? Which ones should have a specific date attached to them?”
Prepare for Meeting One “I am a CEO preparing to run a long-range planning session where my role is to facilitate, not lead. Our industry is [X]. Help me design a 3-hour agenda that guides my executive team to construct a 20-year aspiration themselves, without me imposing a conclusion. Include the questions I should ask — and the ones I should resist asking.”
Surface your team’s hidden assumptions “Here are the key assumptions embedded in our strategy: [list them]. For each one, challenge me to convert it from an open-ended belief into a dated, falsifiable claim. Then identify which assumptions, if wrong, would most significantly change our direction or timeline.”
Run the compression question “Here is a summary of our long-range plan: [paste summary]. Assume the logic is sound. Now help me identify: which parts of this plan are paced by genuine external constraints, and which are paced by internal inertia or conservative thinking? Where could the timeline realistically compress — and what would have to be true for that to happen?”
Build your resilience map “Based on the strategic plan below [paste], identify the three to five external disruptions — technology shifts, market changes, regulatory moves — most likely to force an acceleration of our timeline. For each, describe what an already-prepared organization would do in the first 90 days, versus one that had never considered the scenario.”
Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move.
But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass.
This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause.
The Real Problem Is Sequence, Not Ambition
CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void.
Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does.
Neither framing is quite right. In the end, CEO’s migrate towards short-term goals because they don’t have a reliable way to maintain both short-, mid-, and long-term momentum.
The deeper issue is that most organizations try to do too much in a single planning meeting.
Effective accomplishment of all three phases at the same time requires two distinct meetings, held weeks apart, each demanding a different posture from the leader. Getting the sequence right changes what the plan is, who owns it, and how fast it can move.
Clarifying Misconceptions About Long Horizons
Before the two meetings make sense, two widespread beliefs need to be addressed:
the first is that long-range planning is inherently vague, and therefore not worth taking seriously.
Mistake 1) This is a problem for CEOs who truly have big aspirations, because long-range planning calls for the decades needed to make breakthrough goals realistic and credible to stakeholders. Without adequate time, executives play the game mentioned before. They show up, nod, and wait for the pressure to disappear.
This view of long-range planning being vague is understandable but technically wrong.
The planning tools appropriate for year one of a strategy are genuinely different from those suited to year twenty-five — but that doesn’t mean the far end of the horizon is a guess. It just needs to be equipped in the right way.
For example, the Rolling Wave Technique leads to the use of different methods, mindsets and discussions for short- and long-term phases. It provides operational details in the short term, and higher-altitude targets and milestones in the long term.
Neither end is more rigorous than the other. They are rigorous in different ways. The confusion exists because precious few use the technique. It’s just not taught in most business schools as a component of corporate strategy.
Mistake 2) The second faulty belief is that long-term aspirations don’t matter. To explain why this is so wrong, consider a historical example.
Medieval cathedral builders routinely committed to projects spanning two to three centuries. No individual craftsman who broke ground would see the finished nave. Yet construction continued across generations, through plagues and political upheaval, because the aspiration was large enough to give the work meaning — and specific enough to give it credible direction. Floor plans existed. Proportions were specified. Progress was measurable even when the endpoint was a lifetime away.
This points to a counterintuitive truth: the grander the ambition, the more likely it is to unlock discretionary effort — the creativity and energy people typically reserve for pursuits they actually care about.
Modest, short-term goals produce compliance. In corporate life, these tend to be overwhelmingly financial.
Transformative goals, properly constructed, produce ownership. The audacity of a well-chosen endpoint is itself a management tool, one that most corporations never pick up.
With these misconceptions cleared up, here are the details of both meetings and how they are conducted.
Meeting One: The CEO Goes Quiet
The first meeting has one non-negotiable design principle: the CEO sponsors but does not lead. Or facilitate.
This is harder than it sounds. Most executives who have reached the top of an organization have done so partly through the force of their vision. They arrive at planning sessions having already formed views about where the company should go. The instinct is to share those views early — to inspire the team with a compelling picture of the future and let the session fill in the details.
Resist it. Completely.
The goals of this first meeting are for the executive team to construct the long-range aspiration themselves and define the means to accomplish it. That means choosing a target year — somewhere between fifteen and thirty years out — and then building the assumptions, scenarios, and numbers required to define what success looks like at that point.
It’s followed by the use of the Rolling Wave Technique to lay out a plan for the entire horizon, with more details in closer than later years.
Facilitators can guide the process. The CEO’s role is to hold the space while that process unfolds, tolerating the discomfort of an outcome they did not pre-select and cannot entirely predict.
What makes this worthwhile is what it produces: genuine co-ownership. Every figure the team debated, they will later defend. Every scenario they stress-tested, they trust because they built it. A strategic target and plan defined by the CEO and handed to the team is a document. A strategy the team constructed is a commitment — and the difference shows up in execution, not in the planning room.
For example, one team member assumes a technology shift in five years. Another assumes fifteen. Both assumptions are driving their instincts about investment and timing, silently, in every meeting they attend. Naming those beliefs, debating them, and converting them into dated claims is one of the most underrated outputs of a well-run long-range planning session. It also reveals where the team’s consensus is genuine and where it is merely polite.
Meeting Two: The CEO Becomes an Instigator
Several weeks after the first meeting — long enough for the plan to feel real, not so long that momentum fades — the CEO calls a second session. It has a single agenda item, framed as a question:
“Using the same logic we built together, how much faster could we realistically get there?”
The phrasing matters more than it might appear. This is not a demand for “twice the output in half the time” — the kind of arbitrary stretch target that produces creative accounting and quiet cynicism. It is an invitation to apply the team’s own reasoning to a compression problem. They set the destination and the pathway. Now they are being asked whether the chosen route is as efficient as it could be.
And because the team built the original logic, they are the only people positioned to answer the question credibly. They know which assumptions were conservative. They know where interdependencies between units create natural leverage — and where they create drag. They know which technologies on the industry’s horizon could compress a transition the plan assumed would take a decade. They know where the plan padded timelines because of organizational inertia rather than genuine constraint.
That collective intelligence almost never gets activated, because the question that unlocks it is almost never asked. Unfortunately, leaders tend to apply pressure before the team has built the logic, which means compression becomes a negotiation rather than an analysis. The two-meeting sequence reverses that order — and the difference in what the team produces is striking.
The best version of this second meeting doesn’t only produce a revised plan. It produces a set of credible acceleration options: specific conditions under which the timeline compresses, specific investments or decisions that could trigger those conditions, and an honest accounting of what would have to be true for the faster scenario to hold. The team leaves not just aligned, but strategically fluent in a way that one-off retreats almost never achieve.
Case in point: Before 2017, one of my clients in the Jamaican financial sector had never put a date to an assumption: “the average local customer is not ready for online services.”
When I challenged them to place a date on the moment when 50% of the population would reach that threshold, they predicted: 2028. They wove that date into their plan.
Three years later when the COVID-19 pandemic arrived, that plan was simply accelerated (i.e. compressed) to be implemented within months rather than a decade. They were lucky.
The Resilience Dividend
There is a benefit to this process that rarely appears in planning frameworks: the organization becomes significantly harder to surprise.
An executive team that has jointly built a long-range plan, surfaced its embedded assumptions, dated them, stress-tested scenarios, and explored acceleration options has essentially pre-thought a wide range of futures.
When the external environment forces their hand — a market disruption, a technology shift, a crisis that compresses years into months — they are not improvising. They are activating a version of something they already worked through. The decisions feel fast because they had already built the internal logic needed to respond.
This is not a theoretical benefit. Organizations routinely discover, under pressure, that their plans contained a faster path they simply hadn’t chosen to pursue yet. The companies best positioned to accelerate in a crisis are the ones that already knew, in principle, how acceleration was possible — because they had asked themselves exactly that question before one was forced on them.
The slow work of building shared logic, it turns out, is what makes rapid response possible. Resilience isn’t built in the crisis. It’s built in the room, in the meeting before the meeting, when the CEO is quiet enough to let the team think.
Why This Rarely Happens — and What to Do About It
The reason most aspirations which require long-term strategies end up stalling is that the people accountable for executing them never felt genuinely accountable for creating them. The CEO’s vision, however compelling, remains the CEO’s vision. Rollout becomes performance. Compliance replaces conviction. And when conditions change, there is no one in the room who feels responsible for updating the logic — because the logic was never theirs.
The two-meeting structure addresses this not through a motivational technique but through a structural one. Ownership is built in at the design stage. The compression question in the second meeting then activates that ownership, rather than challenging it.
The process asks something genuinely difficult of the CEO: to be quiet and patient at the moment when they most want to speak, and to ask a question — rather than issue an instruction — at the moment when they most want to apply pressure. Both moves feel counterintuitive. Both, consistently, work.
Begin with the meeting where you say less than you ever have before. What comes next will surprise you.
Use These LLM Prompts to Apply This Framework
Copy any of the following into an AI assistant to put the ideas in this article to work for your organization.
Pressure-test your current strategy “Here is our current strategic plan: [paste or summarize]. Using the Rolling Wave principle from the article I just read, identify where our plan conflates short-, mid-, and long-term planning into a single approach. What assumptions are we treating as facts? Which ones should have a specific date attached to them?”
Prepare for Meeting One “I am a CEO preparing to run a long-range planning session where my role is to facilitate, not lead. Our industry is [X]. Help me design a 3-hour agenda that guides my executive team to construct a 20-year aspiration themselves, without me imposing a conclusion. Include the questions I should ask — and the ones I should resist asking.”
Surface your team’s hidden assumptions “Here are the key assumptions embedded in our strategy: [list them]. For each one, challenge me to convert it from an open-ended belief into a dated, falsifiable claim. Then identify which assumptions, if wrong, would most significantly change our direction or timeline.”
Run the compression question “Here is a summary of our long-range plan: [paste summary]. Assume the logic is sound. Now help me identify: which parts of this plan are paced by genuine external constraints, and which are paced by internal inertia or conservative thinking? Where could the timeline realistically compress — and what would have to be true for that to happen?”
Build your resilience map “Based on the strategic plan below [paste], identify the three to five external disruptions — technology shifts, market changes, regulatory moves — most likely to force an acceleration of our timeline. For each, describe what an already-prepared organization would do in the first 90 days, versus one that had never considered the scenario.”
