The student raised her hand halfway through the session on positioning strategy.
“If the research shows customers want this feature,” she said, “and we can deliver it profitably, why wouldn’t we just launch it?”
It’s the kind of question that sounds simple.
Until you realize you don’t have a simple answer.
Not because the answer is complicated. Because the honest answer reveals something about how decisions actually work that doesn’t fit neatly into the framework we’d just spent an hour discussing.
I paused.
And in that pause, I realized something had shifted in me over twenty years that I hadn’t quite noticed until that moment.
I’d stopped asking questions like that.
What Twenty Years Teaches You
After enough time in commercial roles—sales, procurement, leadership across consumer and B2B businesses—you develop a kind of organizational fluency.
You learn to read rooms. To sense which proposals will survive and which won’t. To understand that the written strategy and the actual strategy are related but different things.
You stop proposing the optimal solution.
You start proposing the optimal solution that can actually happen given everything else the organization is managing.
This isn’t cynicism.
It’s pattern recognition.
You’ve sat in enough meetings to know that launching a new product isn’t just a marketing decision. It touches procurement’s supplier relationships, finance’s margin requirements, operations’ capacity constraints, and sales’ existing customer commitments.
The customer insight is still true.
It’s just not the only truth in the room.
And over time, you learn to integrate all these truths simultaneously. To think in systems rather than functions. To see strategy as the art of the possible, not the theoretically optimal.
This is valuable knowledge.
But teaching revealed it came with a cost I hadn’t noticed.
The Gift of Naive Questions
Students ask questions that sound obvious.
If customers want X, why not give them X?
If the data supports this direction, why choose another?
If this positioning is stronger, why not use it?
After years of practice, these questions can feel… incomplete. Like they’re missing half the picture.
But here’s what I realized teaching them:
They’re not missing anything.
They’re asking the question exactly right.
I was the one who’d learned to automatically append invisible clauses:
“…given our current supplier contracts” “…within our existing operational constraints"
"…without disrupting relationships that took years to build” “…assuming we can’t change anything structural”
Those clauses had become so automatic I’d stopped hearing them.
The students forced me to hear them again.
The Double Translation
There’s a strange thing that happens when you teach strategy after practicing it.
You find yourself translating twice.
First: translating messy business reality into clean frameworks for students to learn.
Then: translating their clean questions back into messy reality to answer them honestly.
One semester, we analyzed why established retailers struggled with e-commerce.
The case was clear. The strategy was obvious. The students identified it immediately: focus on your strongest categories, build premium positioning, optimize for profitability over assortment breadth.
“Perfect,” I said. “So why don’t they do it?”
Silence.
Not because they didn’t know. Because they thought they’d already answered the question.
And they had—from the customer perspective.
What they hadn’t learned yet was that marketing strategy rarely fails because marketers don’t understand customers.
It fails because organizations are ecosystems where every function has already made commitments that constrain what marketing can do.
I could see them trying to understand.
Not why the strategy was wrong—they knew it wasn’t wrong.
Why having the right answer wasn’t enough.
What the Classroom Revealed
Teaching didn’t make me cynical about business.
It made me realize how much complexity I’d normalized.
In one role managing P&L for a regional business, I rebuilt an entire digital channel. Tripled revenue in months. Everyone called it a marketing success.
Looking back through a teaching lens, I could see more clearly:
The marketing was the easiest part.
What made it work was convincing procurement to restructure supplier payment terms. Negotiating with operations to accept different fulfillment economics. Getting finance to approve margin structures that looked worse on paper but worked better in practice.
The marketing strategy I’d have written for a case study would have focused on customer journey optimization and digital positioning.
But that’s not really what happened.
What happened was figuring out how to align six different organizational functions around a customer insight—and then translating that alignment into marketing language so it made sense to everyone.
This is valuable work.
Essential work.
But it’s not what the textbook says marketing is.
The Productive Tension
Here’s what I came to appreciate:
The gap between classroom theory and business practice isn’t a failure of the theory.
It’s the space where judgment lives.
Students need to learn the frameworks. How to think about positioning, segmentation, value creation. How to build strategy from customer insight.
Practitioners need to learn when frameworks apply and when they don’t. How to adapt principles to constraints. How to recognize which constraints are real and which are just inertia pretending to be necessity.
Both are true.
The student asking “why wouldn’t we just launch what customers want?” isn’t naive.
She’s asking the question that should always be asked first.
The practitioner answering “because of supplier constraints and sales relationships and margin requirements” isn’t cynical.
He’s describing the reality that has to be navigated.
The interesting work lives in that tension.
What Changed in How I Taught
By my third year, I’d stopped pretending the frameworks explained everything.
When students asked why the optimal strategy wasn’t chosen, I’d say:
“You’re right. From a pure market positioning perspective, that would be stronger.”
Then: “Here are the organizational realities that usually constrain that choice.”
Not to discourage them. To prepare them.
Because the gap between theory and practice isn’t something you overcome with more experience.
It’s something you learn to work with.
The best strategists I’ve worked with aren’t the ones who ignore organizational constraints.
They’re the ones who find creative ways to honor both customer insight and operational reality—and occasionally, to change which constraints the organization accepts as fixed.
The Question That Stayed With Me
Six months after teaching positioning strategy, a former student reached out.
She’d conducted customer research at her first marketing role. Built a repositioning strategy. Presented it to leadership.
“They said it was excellent,” she told me. “Then chose a different direction.”
I recognized the confusion in her voice.
Not anger. Just the disorientation of watching the right answer get passed over for reasons that weren’t quite explained.
“Were they wrong?” she asked.
This is the question I’d learned to answer differently.
Early in my career, I would have said: yes, obviously, the data was clear.
After twenty years, I might have said: no, they had strategic context you’re not seeing yet.
But teaching had given me a third answer:
“Both things can be true. Your strategy could be better for customers and their decision could still be the right organizational choice in that moment. The skill isn’t choosing between those two perspectives. It’s learning when each one matters more.”
She thought about that.
“So how do you know which one matters more?”
“You usually don’t,” I said. “You make the best case you can for the customer perspective, understand the organizational constraints, and learn from what happens either way.”
It wasn’t the clean answer she wanted.
But it was the honest one.
What I Carry From Both Worlds
I’m grateful for the years in the boardroom.
They taught me how decisions actually get made. How strategy works in practice. How to navigate complexity without losing sight of purpose.
I’m equally grateful for the years in the classroom.
They reminded me that the complexity I’d learned to navigate had also become invisible to me.
That questions that sound simple often are simple—and our sophisticated explanations for why they’re not are sometimes just rationalizations for maintaining the status quo.
That customer-centric thinking isn’t naive. It’s the anchor that keeps all the necessary compromise from drifting into pure internal optimization.
The boardroom teaches you what’s possible.
The classroom reminds you what should be possible.
Both perspectives matter.
The challenge is holding them simultaneously without letting one erase the other.
I still teach the frameworks.
Positioning strategy. Customer segmentation. Value proposition design.
But now I teach them differently.
Not as blueprints that guarantee outcomes.
As languages for having better conversations about what matters.
The students who succeed aren’t the ones who follow the frameworks most precisely.
They’re the ones who learn when to apply them, when to adapt them, and—occasionally—when to set them aside and ask the simple question everyone else has stopped asking.
If customers want this, why wouldn’t we just give it to them?
Sometimes there are good reasons.
Sometimes there aren’t.
The hard part is staying curious enough to know the difference.