Writing As Understanding, Not Solution: Why Diagnosis Beats Prescription
Lesson 8 of 25 from podcast conversations with leaders who leave the world better than they found it
Koye Oyeyinka writes fiction. But when he talks about his writing, he's not talking about creativity or self-expression. He's talking about understanding.
"Strategy, like storytelling, is less about solving problems than about truly understanding them," he told me.
He writes characters he doesn't immediately understand. People who make choices that seem irrational on the surface. And through writing them—through trying to create a coherent internal logic for their behavior—he develops genuine comprehension of what drives them.
He's not trying to fix them. He's trying to understand them.
And that distinction matters more than we realize in organizational strategy.
The Rush To Solutions
I've been in many strategy meetings that follow this pattern:
Someone describes a problem. Before they've finished explaining it, people are raising hands with solutions. Ideas fly. Energy builds. Everyone feels productive.
We leave the meeting with an action plan.
Six months later, the problem persists.
Here's why: we solved a problem we didn't actually understand.
We treated the symptoms. We implemented the obvious solution. We acted quickly and decisively.
But we never asked whether we'd correctly diagnosed what was actually happening.
Most organizations spend maybe 10% of their strategic planning time on problem diagnosis and 90% on solution generation.
That ratio should be reversed.
Why We Skip Diagnosis
There are good reasons we rush past diagnosis:
Solutions feel productive. Sitting with a problem, trying to understand it deeply—that feels passive. Generating solutions feels active.
Diagnosis is uncomfortable. Real diagnosis often reveals that the problem is more complex than we want it to be. Or that we're part of creating the problem. Or that solving it requires changes we're not ready to make.
We're incentivized to act. Boards want to see action. Funders want to see innovation. Staff want to see leadership making decisions. Nobody's asking "did you really understand the problem?"
We assume we already know. We've been living with this problem. We've watched it play out. Of course we understand it. Why waste time on diagnosis?
But assumption isn't comprehension. And shallow understanding leads to shallow solutions.
What Deep Diagnosis Looks Like
Koye's approach to fiction offers a model for strategic thinking:
Start with observation. What's actually happening? Not what you think is happening. Not what should be happening. What is demonstrably, observably occurring?
Look for patterns. How long has this been happening? Under what conditions does it get better or worse? Who's affected and how?
Explore multiple explanations. What are three different ways to make sense of this situation? Not which one is right—just what are the possibilities?
Test your understanding. If your diagnosis is correct, what else would you expect to see? Does that match reality?
Sit with uncertainty. Sometimes you have to live with a problem longer before you understand it well enough to solve it properly.
This takes time. It feels slow. It requires resisting the pressure to move to action.
But problems that have been around for years aren't going to be solved by quick analysis. They require deep comprehension.
The Strategy Meeting That Changed My Approach
Here’s an example about a workforce development organization.
They were struggling with participant retention. People would start the program excited, then drop out halfway through.
The immediate solutions were obvious: more support services, better screening to accept only highly motivated candidates, financial incentives for completion.
But the executive director pushed the team to spend more time on diagnosis first.
"Before we solve it, let's make sure we understand it," she said. "Let's talk to people who dropped out. Let's look at patterns—when do people leave? Who stays? What's different about their experiences?"
The team resisted. This felt slow. They wanted to act.
But she held firm. They spent two full meetings just trying to understand the problem.
And what they discovered changed everything.
The dropouts weren't unmotivated. They were getting jobs. Entry-level jobs that required immediate start dates. Jobs that didn't pay well but paid better than nothing.
The program was designed for people to complete before entering the workforce. But their participants were already in the workforce—working multiple part-time jobs. They were joining the program to access better opportunities, but when an immediate opportunity appeared, they took it.
The problem wasn't lack of commitment. It was that the program design didn't match participant reality.
None of the "obvious" solutions would have addressed the actual issue.
More support services? Irrelevant. Better screening? Would have excluded exactly the people they wanted to serve. Financial incentives? Not competitive with actual employment.
The real solution was different: flexible scheduling that allowed people to work while training. Partnerships with employers who would hire participants mid-program. Credential-stacking that created value at multiple exit points.
But they only got to those solutions by spending time truly understanding the problem.
The Exercise That Forces Understanding
Here's what I want you to try at your next strategic planning meeting:
Change the time allocation.
Normally, strategy meetings work like this:
20 minutes describing the problem
90 minutes generating and evaluating solutions
Reverse it:
90 minutes exploring and diagnosing the problem
20 minutes identifying next steps
That 90 minutes should include:
Gathering data. What do we actually know? What are we assuming? What would we need to know to be confident in our understanding?
Exploring competing explanations. What are three different ways to make sense of this situation?
Testing hypotheses. If explanation A is correct, what else would we expect to see? Does that match reality? What about explanations B and C?
Identifying gaps. What don't we understand yet? Who could help us understand it better? What would it take to get that understanding?
You might not get to solutions in that meeting. That's okay.
Because when you truly understand a problem, the solutions often become obvious. And when solutions aren't obvious, that tells you your understanding isn't deep enough yet.
Why This Matters For Strategic Impact
The organizations I've seen achieve the most significant impact aren't the ones that move fastest or generate the most creative solutions.
They're the ones that invest in understanding problems deeply before trying to solve them.
They ask "why" more than "what should we do?"
They sit with complexity instead of rushing to simplify.
They're comfortable with uncertainty longer than most organizations can tolerate.
And because of that patience, when they do move to action, they're solving the actual problem. Not the surface symptom. Not the obvious issue. The root cause.
That's what Koye's fiction practice teaches: understanding precedes solving.
You can't write a coherent character until you understand their internal logic. You can't implement sustainable change until you understand the system's internal logic.
The writing—the solution generation—comes after comprehension, not before it.
From Solutions To Understanding
Most strategy fails not because of bad solutions, but because of shallow diagnosis.
We solve the wrong problem effectively. We implement the obvious solution to a misunderstood situation. We act quickly on insufficient understanding.
Next time your team identifies a strategic challenge, resist the urge to jump immediately to solutions.
Ask: how confident are we that we understand what's actually happening here?
If the answer is anything less than "very," spend more time on diagnosis.
Talk to people experiencing the problem. Look for patterns. Explore multiple explanations. Test your hypotheses.
Sit with the uncertainty until understanding becomes clear.
Because strategic thinking isn't about clever solutions.
It's about accurate diagnosis.
This is lesson 8 in a 25-part series exploring insights from podcast conversations with leaders who leave the world better than they found it.
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