We call it Artificial Intelligence, but large language models don’t think, reason, or understand in human terms.
A more accurate description might be Artificial Idea Iteration since these tools dramatically compress the cycles of research, drafting, testing, and revision.
SpaceX didn’t transform spaceflight by having perfect ideas. They collapsed the time between ideas and reality. Failing fast, learning quickly, and iterating relentlessly.
AI creates the same dynamic for knowledge work, letting us move from intuition to articulation to revision in hours instead of weeks.
Engineers rely on wind tunnels to test aircraft designs before committing real materials and lives. AI does this for thinking.
Iteration itself isn’t new. What’s new is the scale for iteration that we now have at our fingertips. We can explore multiple paths, abandon weak directions quickly, and refine promising ones without the time, coordination, and risk that once kept ideas locked in our heads.
When iteration becomes inexpensive, we can take more intellectual risks and shift from trying to always be right to trying to always get better.
It’s ironic that as iteration is becoming cheaper and faster with AI tools, human judgment becomes more valuable. Someone still needs to know what’s worth developing, what deserves refinement, and when something is complete rather than exhausted.
The intelligence was never in the machine. AI simply gives us the capacity to develop ideas, test them against reality, and learn from the results at a scale and speed we’ve never had before.
Photo by SpaceX on Unsplash – when SpaceX proposed the idea of landing and reusing their rocket boosters after each launch, the idea seemed impossible. Now it’s happening about 3 times per week…and they’re just getting started.
We turn it over in our head. We ask a few more questions. We look for one more data point. We check with another person whose opinion we respect. We wait for the timing to feel right.
And still, we hesitate.
We tell ourselves we need more information. More time. More certainty.
Indecision usually grows from very human places. Fear of being wrong. Fear of being blamed. Fear of choosing a path that can’t be undone. Fear of embarrassment.
Add decision fatigue to the mix and postponement starts to feel reasonable.
Meanwhile, the cost of waiting accumulates quietly. Teams stall. Momentum fades. Confidence erodes. What began as a thoughtful pause turns into drift.
Most leadership decisions are made without perfect information. Progress rarely waits for certainty.
So, what is our hesitation really telling us?
Sometimes, it’s a clear no. A request pulls us away from what matters most. We don’t like what we see, but we’re not sure why. Maybe a partnership doesn’t sit right with our values. In these moments, extended thinking isn’t searching for clarity. It’s searching for a way to explain our decision.
Other times, we hesitate because the decision stretches us. It introduces uncertainty. It raises our visibility. It asks more of us than we feel ready to give. Growth decisions usually feel uncomfortable before they feel right.
At some point, the data stops improving and the waiting stops helping.
Start small. Take a step that tests the decision rather than locking it in. Forward motion reveals new information…something thinking alone can’t.
A decision that turns out to be wrong isn’t failure.
It’s feedback.
And feedback points us toward our next decision.
“Whenever you see a successful business, someone once made a courageous decision.” — Peter F. Drucker
Photo by ChatGPT’s new image generator, which is way better than prior versions of the tool.
Some leaders wear the line outside their door like a badge of honor. People waiting with questions, approvals, decisions.
It feels like proof of trust. Proof of competence. Proof of necessity. If the team can’t move forward without your judgment, surely that means you are at the center of the work.
In many ways, you are.
But there’s a second truth hidden inside that scene. When every decision depends on you, you become the one point your organization can’t outrun.
The line reveals the fragility that forms when decisions stay in one place instead of growing across the organization.
At a certain level of responsibility, leadership effectiveness isn’t measured by the number of good decisions you make. It’s measured by whether the organization can make good decisions without you having to approve each one.
Leadership at this level is staying at the wheel while helping others learn to steer.
High-pressure operators know instinctively that a bad decision leaves a mark. A slow decision leaves a gap. Most organizations struggle more with waiting than with trying. That line at your door, day after day, is the quiet proof. The whole operation can only move as fast as the person at the center of its decisions.
There’s a time in every leader’s career when the instinct to take control is the right one. When the team is inexperienced, when stakes are high, when the risk is real and present, you become the center of gravity because someone has to be.
But later, if the business grows and the structure doesn’t change, this habit of control becomes limiting. What protected the organization early can start to quietly cap its potential, because your bandwidth is finite.
There’s a moment when the senior leader’s job shifts from “Do we have the right answer today?”to “Will we have the right judgment tomorrow?”
That shift feels slow. It feels inefficient. It feels like a luxury.
It isn’t.
It’s a protective move.
Teaching someone how to make a decision can feel like taking the long way around the problem. You could make the call in 30 seconds. Walking someone through the context and reasoning might take half an hour.
It’s natural to skip teaching and just decide. It feels faster. And today, it is.
But tomorrow it isn’t. Because they come back with the next decision. And the next. And the line gets longer.
Here’s a simple practice that changes the arc of your relationship without exposing the business to risk. When someone comes to you with a decision, don’t give the answer first. Ask them, “What would you do?”
You’re not surrendering the decision. You’re building their capacity to make it. You’re seeing how they think. You’re catching errors before they matter. You’re adding the perspective that builds judgment.
It is controlled delegation, not abandonment. Nothing is handed off recklessly.
When someone brings an answer that is close to right, you supply the context they don’t have, and then you say something specific and concrete:
“Next time this situation comes up, you can make that decision.”
Not in general. Not theoretically. For this exact decision, with a shared understanding of why it works.
Over time, the pattern shifts. Fewer decisions reach you. The ones that do are larger, higher consequence, more strategic. The team develops in the shadow of your reasoning, not separate from it. And the bench of judgment widens beneath you.
This is what protects the business from single-threaded leadership. Not a gesture toward empowerment, but a strategy of risk reduction.
Leaders don’t become less important by creating decision-makers. They become less fragile.
The organization becomes capable of sound judgment when you’re not there. The most durable form of control a leader creates.
If the business only works at full strength when you are present, you haven’t reduced the risk. You’ve concentrated it.
At the top levels of leadership, the question is rarely, “Can you decide?”Of course you can.
The real question is, “Can others decide well when you aren’t in the room?”
That’s the difference between being the operator and building the operation.
It begins quietly. A question reflected back. A recommendation explored. A context added. A decision shared. A leader shaped, one situation at a time.
The line at your door gets shorter and your organization gains strength. Not because you step away from accountability, but because you’ve built accountability into the people who stand in that line.
Leadership Homework
One question to sit with, without rationalizing it away:
If you disappeared for 30 days, what decisions would the organization be unable to make without you?
Not decisions they might make differently, different is acceptable. Decisions they could not make.
That answer will show you where the real bottleneck lives.
And where the next generation of leadership needs your attention.
I’ve come to believe what Chesterton once said. Art is limitation, and the essence of every picture is the frame. It took me time to see that truth.
Many of us grow up thinking freedom creates great work. Unlimited time. Unlimited canvas. Unlimited choice.
But if you’ve ever stared too long at a blank page, you know what real freedom can feel like. Paralyzing.
Nothing takes shape until the edges appear. A story waits forever if the writer can’t decide where it begins. Music is noisy until the composer chooses a key. The frame gives the work its purpose.
The same is true in leadership and life. A budget helps us decide what we value. A deadline turns a dream into something real. A small team learns to trade excess for imagination. Limited resources push us to invent new ways to adapt. The frame brings focus.
Still, the frame itself matters. A picture can feel cramped when the frame becomes too tight. A project can drift when the wrong thing fills the center. When the boundaries are off, the whole image loses clarity. That’s why wise leaders spend time defining the edges before the work begins.
Whenever I work on a puzzle, I start by finding all the edge pieces. Once the border comes together, I can see how everything else might fit. The same principle applies to creative work and leadership. The edges give us context. They help us imagine where the middle pieces belong and how the picture will come to life.
Frames should change as we grow. The world shifts. We learn more about what we’re building. Every so often, we step back and see whether the picture still fits. Sometimes the frame needs widening. Sometimes the colors need more light. Adjusting the frame keeps the beauty true.
Constraints give possibility its shape. They reveal what truly matters. Choosing the right limitations helps us see what is essential.
When you feel boxed in or limited, pause before you push against the edges. The frame around your work may be the very thing helping the picture appear. And when the picture becomes clear, refresh the frame so the beauty within it continues to grow.
Thanks to James Clear for sharing this G. K. Chesterton quote: “Art is limitation; the essence of every picture is the frame.”
The difference between reacting to the moment and preparing for it.
Most leaders spend their days responding. A problem surfaces. They fix it. A crisis hits. They mobilize.
Urgency crowds out importance. By Friday they’re exhausted from fighting fires they never saw coming.
This is leadership without anticipation.
Every action sets something in motion.
-Launch a product without considering support capacity, and you’ll be drowning in angry customers in three months.
-Promote someone before they’re ready, and you’ll spend the next year managing the fallout.
-Ignore the quiet signals in your market, and you’ll wake up one day wondering how you got disrupted.
Some outcomes can be seen in advance. Leadership is the discipline of noticing what’s coming and readying your team to meet it.
Wayne Gretzky once said, “I skate to where the puck is going to be, not where it has been.”Most leaders skate to where the puck was. They optimize for yesterday’s problem. They staff for last quarter’s workload. They strategize for a market that no longer exists.
Leaders who matter skate differently. They think past the first step and see how decisions unfold across time. When they make a choice today, they’re already anticipating the second and third-order effects.
They connect short-term actions to long-term outcomes, asking not just “Will this work?” but “What happens after it works?”
When you cultivate this habit of anticipation, something shifts. You stop being surprised by the predictable. You create space before you need it. You move with a quiet confidence that comes from seeing the terrain before you cross it.
Your team feels it too. It’s the difference between reactive and ready, between scrambling and intentional.
We can’t eliminate uncertainty. The future will always bring surprises. But we can change how we manage it. We can choose to be the leader who sees what’s coming rather than the one who’s perpetually caught off guard.
Dwight Eisenhower said, “In preparing for battle I have always found that plans are useless, but planning is indispensable.” Plans will change. They always do. But the act of planning, of thinking through trajectories, testing assumptions, and imagining scenarios, prepares you to lead when the moment arrives.
The leader who anticipates doesn’t wait for clarity. They sense it forming and courageously move toward it. They shape the path while others are still reacting to it.
It was the second day of a two-day strategic planning retreat. Revenue projections stretched across the screen. The CFO walked through all the assumptions in his spreadsheet. Customer acquisition costs will flatten, churn will improve by two points, and the new product will capture eight percent market share within six months.
Everyone nodded along, acting as if these forecasts represented knowledge rather than elaborate guesses built on dozens of assumptions, any one of which could be wrong.
Three months later, a competitor launched an unexpected feature. Customer behavior shifted. The CFO’s projections became relics of a reality that never existed. The entire strategic planning process had been built on an illusion.
What we pretend to know
In his 2022 memo The Illusion of Knowledge, Howard Marks explored how investors mistake confidence for clarity. He began with a line from historian Daniel Boorstin:
“The greatest enemy of knowledge is not ignorance, it is the illusion of knowledge.”
Leaders face a brutal paradox. Boards expect forecasts. Teams want confidence. Investors demand projections. The machinery of leadership demands certainty.
So, we build elaborate forecasts and make decisions based on assumptions we know to be fragile. We treat detailed guesses as facts.
Physicist Richard Feynman once said, “Imagine how much harder physics would be if electrons had feelings.” Electrons follow discrete laws, unlike people. People innovate, resist, panic, and occasionally do something amazing nobody saw coming. Competitors behave differently than our models assume. Markets shift for reasons we never thought possible.
Marks describes forecasting as a chain of predictions. “I predict the economy will do A. If A happens, interest rates should do B. With interest rates of B, the stock market should do C.” Even if you’re right two-thirds of the time at each step, your chance of getting all three predictions correct at once is only about thirty percent.
Leadership forecasts work in a similar way. We predict customer adoption rates. If adoption hits those numbers, we’ll need a certain operational capacity. With that capacity, we can achieve specific margins. Those margins will attract investment.
Each assumption depends on the previous one. The chain is only as strong as its weakest link.
The tools we trust
Walk into any strategic planning session and you’ll likely encounter two frameworks treated as gospel:
-SWOT analysis (strengths, weaknesses, opportunities, and threats)
-SMART goals (specific, measurable, achievable, relevant, and time-bound).
Business schools teach them. Consultants recommend them. Leaders deploy them with confidence. Each relies on assumed knowledge that may not exist.
A SWOT analysis claims to know which possible developments count as opportunities versus threats. It’s a snapshot of assumptions masquerading as strategic insight. An opportunity exists only if you can identify it, execute against it, and do so before circumstances change. The framework provides no way of acknowledging uncertainty.
SMART goals often confuse precision with accuracy. “Increase market share” becomes “increase market share in the Northeast region from 12% to 15% by Q4 2026.” It sounds specific, and therefore rigorous. It’s easy to be precise about something unpredictable.
And how do we know a goal is achievable? We make assumptions about resources, market conditions, and competitor behavior, then write a goal that treats our assumptions as facts.
Both frameworks serve a valuable purpose. They force structured thinking. But they also seduce leaders into believing they know more than they do.
What should we do instead?
To be clear, this isn’t an argument for abandoning planning. Organizations need direction, priorities, and coordinated action. The question is how to plan in ways that acknowledge what we can’t know while still making decisive progress.
A better path involves changing how we plan and how we talk about the future.
Distinguish between direction and destination. Amazon knew it wanted to be “Earth’s most customer-centric company” without knowing exactly what that would look like in year ten. “We’re moving toward increased automation” carries more truth than “we’ll reduce costs by seventeen percent by Q3 2026.” The first creates direction. The second creates false precision.
Separate what you know from what you assume. Customer complaints increased forty percent this quarter. That’s knowledge. Saying the trend will continue is extrapolation. Predicting that fixing the issue will increase retention by five points is speculation. Present plans that show what you know, what you’re inferring, what you’re assuming, and what you’ll do if you’re wrong.
Build optionality into everything. Create strategies that work across multiple futures. Hire people who can do, or think about, more than one thing. Build modular systems with flexibility in mind. Create decision points where you can change course.
Use familiar tools differently. Run a SWOT analysis, then list three ways each opportunity might fail to materialize. Write SMART goals, then document the assumptions those goals depend on and how you’ll adapt if they prove incorrect.
Here’s a concrete example. You’re deciding whether to build a new product line. The traditional approach creates a detailed business case with market projections and revenue forecasts. You present it. People debate assumptions. A decision gets made.
An alternative approach defines what success means, then identifies what must be true to achieve it. You sort those conditions into things you can validate quickly, things you can validate over time, and things you can validate only much later. Stage investments to match the timing of the validations, rather than an arbitrary quarterly schedule.
The difference in these approaches is critical. In the first, the business case pretends to represent knowledge. In the second, it becomes a set of hypotheses to test over time.
The harder path
Amos Tversky observed, “It’s frightening to think that you might lack knowledge about something, but more frightening to think that, by and large, the world is run by people who have faith that they know exactly what’s going on.”
We select leaders for their ability to project confidence about an unknowable future. We reward decisiveness over doubt. Then we wonder why strategies fail when reality diverges from our projections.
Most of us live in this system. We’ve built organizations that demand the illusion of knowledge.
Real leadership creates organizations resilient enough to find answers as circumstances unfold. It builds teams that can adapt rather than simply execute a plan written many months ago.
When did you last change a forecast because reality diverged from your assumptions?
When did you last reward someone for identifying that a plan was failing?
Start small. Pick one decision where you can be explicit about uncertainty. Structure one investment to test assumptions instead of betting on a forecast. Have one conversation where you separate what you know from what you’re guessing.
Plan in ways that acknowledge uncertainty and position your organization to learn. Lead with confidence about principles while staying adaptable around specifics. Build organizations that can adapt when reality diverges from the plan.
Because it will. The measure of leadership lies in how well your culture can face that truth.
I’m told that this is one of the top questions students (and parents) ask of teachers.
I’m told that this is one of the top questions students (and parents) ask of teachers.
Test questions in school come in many standard forms: true or false, multiple choice, essay…just to name a few. Oh yeah, and word problems! Decipher the riddle, find all the numbers that fit into formulas, and arrive at an answer (hopefully, the correct one). And, of course, remember to show your work.
We’re taught in school that there is only one correct answer to most questions. Columbus discovered the New World in 1492, not 1493. It takes two hydrogens and one oxygen to make water, not two oxygens and one hydrogen. The student’s job is to learn (memorize?) the correct answers and then “ace” their test by answering all of the questions correctly.
It’s no wonder students ask what will be on their tests. After all, their grade is in play. Who wouldn’t want to know what they should study, and what they can ignore? So much is riding on the outcome.
Tests outside of school aren’t as easy. The questions don’t come from our teachers. Variables are often missing, and formulas rarely provide one definitive answer. They aren’t always fair. They don’t come with a study guide. There’s no advice about what should be studied, or ignored. Real life tests come from our family, friends, customers, co-workers, managers, elected officials, our children’s teachers, strangers, and ourselves…on a daily basis. A lot more than a grade is in play with most of these tests.
Attention to detail, listening to what is said and unsaid, curiosity, creativity, openness to risk, connecting with others we trust, and a clear sense of right and wrong are the guides we have in answering the real life test questions we face.
What’ll be on your next test? Everything you’ve experienced in life up to this point, and probably a few things you haven’t seen before. Here’s hoping you studied well.
Test Question: What’s the connection between this post and the sunrise photo?
Grandpa Bob Encouraging Leadership 
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