The AI Researcher: From Information Overload to Active Knowledge Synthesis (Part 1)
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.)
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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).
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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….
Ep 35 – Your Strategic Stagnation Isn’t a Framework Problem—It’s a Story Problem
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
The AI Assistant: Automating Administrative Friction and “Shadow Work”, Part 2
The Two Meetings That Turn Long-Term Strategy Into Motion
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.”

The Two Meetings That Turn Long-Term Strategy Into Motion
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.”

The Two Meetings That Turn Long-Term Strategy Into Motion
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.”

The AI Assistant: Automating Administrative Friction and “Shadow Work”
What Does Perspective Mean in GTD?
What Does in Control Mean in GTD?
In this episode we’re discussing the concept at the core of personal management: control. Specifically, we’ll be philosophizing about what control truly means within the context of the Getting Things Done (GTD) methodology. We’ll start with David Allen’s definition, which ties control to the workflow stages of capturing, clarifying, organizing, reflecting, and engaging. But does that definition fully capture the complex, often psychological, reality of feeling “in control”? Then, we explore how to build tangible systems and “guardrails” that move us from simply feeling overwhelmed to being confidently in command of our work and personal lives.
(If you’re reading this in a podcast directory/app, please visit https://productivitycast.net/145 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 what control means in the context of GTD from this episode, please click here to leave a comment down below (this jumps you to the bottom of the post).
In this Cast | What Does Control Mean in GTD?
Ray Sidney-Smith
Augusto Pinaud
Art Gelwicks
Francis Wade
Show Notes | What Does Control Mean in GTD?
Resources we mention, including links to them, will be provided here. Please listen to the episode for context.
Getting Things Done (GTD) by David Allen
How to Get Control of Your Time in Your Life by Alan Lakein
Freedom.to (A Focus application used to block digital distractions)
Fitbit watch (Used to track sleep)
Byron Katie’s process (A methodology for managing unwanted thoughts or feelings)
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).
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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.
Raymond 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
And I’m Augusto Pinaud.
Francis Wade | 00:26
I’m Francis Wade.
Art Gelwicks | 00:28
And I’m Art Gelwicks.
Raymond Sidney-Smith | 00:29
Welcome, gentlemen, and welcome to our listeners to this episode. Today, we are going to do some philosophizing, I suppose, and hopefully bringing ourselves from that level down to the practical. We’re going to be talking about control. And what I wanted to do was to preface this with The concept of control and perspective in the Getting Things Done or GTD methodology perspective, which is that that’s where came up to me in the first place. And over the years, it has changed. And so I want to talk about what does control mean to each of us and how do we actually make the concept of control practical even tangible in our own worlds. I’m going to define what David Allen says of control in Getting Things Done in the March 2015 edition, in the appendix, in the glossary of Getting Things Done terms, he actually gives a definition for control And then we’re going to talk a little bit about what, the concept of GTD control is so that we can then define what We think of it as in contrasting terms.
So he says of control, one of the two key elements of self and organizational management along with perspective. And so that’s what he calls control in the most basic terms. And if we think about it from the concept of control and perspective, control are the steps of the or stages of the workflow going from capturing to clarifying to organizing, reflecting and engaging on the action level of the horizons of focus. That is what he considers control.
And then as we go up the horizons on the y-axis, we then have projects and so on and so forth going up the horizons. And that’s what he considers perspective.
So control are the actions that we take on the lowest level of the horizons of focus and everything above that becomes perspective. So kind of thinking of it as looking down at the actionability of the thing above itself.
So when you’re at the highest level, Horizon 5 purpose and principle You are looking down at the other’s vision, goals, areas of focus and accountability, projects, and actions. So that is the GTD definition. And… We have all probably thought of it as being insufficient in some way, shape or form in our own worlds. And now what I’d like to do is to ask you all, gentlemen. How do you define control? And what is… If I think Art gave a really great example before we started recording, if someone came to you and said, I’m feeling out of control, how do you help them get in control or under control in their life?
Francis Wade | 03:10
So I think David Allen’s definition is basically a process definition. So he’s saying, here are the steps. Or managing tasks. And the ones that really start with capturing and so forth are basically the steps for managing tasks. And I suppose that I’m guessing that what he means by control is that the… Process of managing tasks is in control. Now, that has a very specific meaning in my world. I was trained in part as an industrial engineer. And we love For those of you who know the Leningrad-Stewart charts and control charts, we love the idea of measuring processes so that they stay in control. That’s not practical for most people to be able to use these kind of diagnostic tools. But the way I would advise to answer your question, Reem, someone who tells me that they’re out of control… Is to ask them What do you mean? Because the word control is a psychological object The definition has changed and it varies and there’s no uniform. Understanding of what it means.
So you have to go to the next step and say, When you say control, the question I would ask is when you say control, What specifically? Symptoms are the ones that you notice and I would imply in real life. Not just in your emotional life, but in The Hard Tensible Life where are those symptoms occurring? Such that you’re led to conclude that you’re feeling out of control.
So I would immediately go to and I would focus and start to break down their response. Between I’ve mentioned psychological objects like I’m feeling stressed, I’m feeling unhappy, I’m feeling unworthy, I’m feeling lazy. As opposed to I arrive at half of my appointments at least ten minutes late. Okay, there we go. That’s one. That’s a tangible object. We can work with that. What else do you have? Well… I wake up in the middle of the night three times out of the week. With something that I forgot to do. That’s two. All right, that’s another tangible activity.
So I would look for the tangible symptoms. The things that you can put your finger on, you can touch, you can see.
And then accumulate those so that we move the conversation from and feeling out of control. Towards And again, in the lingo of industrial engineers is defects. We’re looking for defects. And we’re looking to put them together so that we can say, okay, with these five defects, the root cause of them are Because the truth is, control is a lag indicator. Peely Walter Control is a lag indicator. Comes a lot after. The things that you Did or didn’t do.
So we’re trying to go all the way back so that When we start to… Figure out what they should do, We’re actually looking at things that they did do or need to do or didn’t do. In tangible reality.
So that’s how I would tackle it. Said that to me.
Art Gelwicks | 06:21
Control to me is a very… Unlike the industrial… Definition of it. I look at it from the almost the psychological side of it. Control is a perceived state of comfort It’s a lack of stress. It’s a… Point of awareness. Of activity And I think when someone says they are out of control, my first reaction is to ask the question, When do you feel things went out of control. Because I need to know contextually Is this something that is a recurring feeling, which means that it is probably systemic. To a process failure Or is it something that has recently happened, which may be triggered by an environmental response or some external factor that has pushed things off the rails? But control itself like a, can be an extremely negative impact. On work and process and quality of work. Having a sense of control. I don’t know is necessarily an extremely positive thing. It’s basically neutral. You feel like, okay, if I’m in control, I can do… What I need to do. If I’m out of control, I can’t do what I need to do. But at no point are we saying that if I’m in control, I can do better things. I’m just saying that I can do things.
So to me, I always look at it from the mental aspect of it more than the process one, because The process one I can chase. I mean, I can look at the measures. I can look at the metrics involved and say, OK, this is working. This isn’t this. But that doesn’t necessarily, again, translate to a lack of control. And we’ve all seen it. We’ve had people who have processes that work somewhat. But they feel like they are in control, but we know looking at it, it’s like, no, you’re not. As much as you think you are, you’re careening wildly down the highway.
So… The subjectivity of that term and the amorphousness of that term makes it difficult to have that initial conversation.
Raymond Sidney-Smith | 08:49

