May 10, 1796. The Battle of Lodi. French forces struggled to cross the Adda River under withering Austrian fire, their advance stalled at the narrow bridge. General Bonaparte surveyed the chaos, then did something that shocked his officers—he strode to the artillery positions on the riverbank and began personally asking why their fire was ineffective and helping to direct and sight the cannons, adjusting elevation and trajectory to bombard enemy positions with accuracy and support the desperate assault.

This was work for a corporal or gunner, not a commanding general. But Bonaparte understood something his aristocratic counterparts did not: you cannot improve what you do not comprehend. Having risen through the ranks as an artillery officer since 1785, he knew the precise questions to ask, the exact variables that mattered. His hands-on leadership that day so impressed his troops that they gave him a nickname that would follow him to his grave: “Le Petit Caporal”—The Little Corporal.

Even years later as Emperor, Napoleon would continue this practice, personally sighting artillery pieces during battles. He understood that grand strategy lived or died on such details—on whether a gunner knew to account for muddy soil affecting gun placement, on whether the standardized ammunition actually fit the standardized cannons, on whether his “beautiful daughters” (as he called his beloved 12-pounders) could move with infantry speed.

The Conference Room Problem

How different this is from the scene playing out in countless conference rooms across our modern organizations. A product is failing in the market. Costs are spiraling. Customer satisfaction scores plummet. And so the leaders convene, gathered around polished tables, each announcing the problem from their vantage point. The CFO declares the budget exceeded. The CMO points to competitive pressure. The COO cites operational bottlenecks. Everyone marks their territory, delineates the problem’s boundaries, then waits for someone else to solve it.

But great operational leaders don’t mark problems—they excavate causes and reach to the root cause.

Why Questions Require Experience

There exists a particular skill, rare and invaluable, possessed by leaders who truly understand their organizations from foundation to peak. It is the art of asking the right question. Penetrating question that strips away assumption and drives toward root cause.

Yet here lies a truth we often overlook: the ability to ask the right questions is itself born from experience. A leader who has never wrestled with production bottlenecks doesn’t know to question whether the issue is capacity, sequencing, or quality control. Someone who has never managed a struggling team cannot discern whether low performance stems from unclear objectives, inadequate tools, poor morale, or simple capability mismatch. The right questions emerge only from pattern recognition built through lived experience—from having encountered similar problems before, from having seen how issues manifest and propagate through systems.

This is iterative questioning—a disciplined process of peeling back layers. The machine is running hot. Why? The cooling system is overwhelmed. Why? The throughput increased beyond design parameters. Why? We changed suppliers to cut costs. Why? We assumed cheaper components would perform equivalently. And there, finally, lies the root: a bad assumption, masquerading as prudent cost management.

But notice: each “why” in that sequence requires knowing that the next layer exists. The leader who asks about the cooling system must have the experience to know that thermal management isn’t just about the cooling unit itself—it’s about the entire system’s thermal load. These insights don’t come from books or briefings. They come from having been there, from having made or witnessed such mistakes before.

The Apprenticeship That Cannot Be Skipped

This is why the climb matters so profoundly. It’s not merely about understanding answers when they arrive. It’s about developing the cognitive framework to identify what’s worth questioning in the first place. The leader who has worked through each layer of the organization has built an internal library of patterns: “I’ve seen this symptom before, and when we dug deeper, the real issue was X.”

Consider the leader promoted through merit, who once sat in the trenches troubleshooting production issues, who once negotiated with difficult suppliers, who once had to explain to customers why deadlines were missed. This person carries an encyclopedia of experience—they know which explanations are likely true and which are merely convenient. They recognize when a team is struggling with genuine complexity versus when they’re avoiding accountability. And crucially, they know which questions to ask because they’ve encountered these situations before. Their inquiries are surgical, targeted, informed by countless previous encounters with similar challenges.

Now contrast this with the leader parachuted into position—brilliant perhaps, credentialed certainly, but fundamentally unfamiliar with the terrain. Can such leaders succeed? Sometimes. If they possess genuine curiosity and approach their ignorance with humility, they can, over time, develop the necessary wisdom. But this path is treacherous. Most often, lacking the intuition born of experience, they don’t even know what they don’t know. They accept the first plausible explanation because they lack the pattern recognition to sense when something doesn’t quite add up.

The Crisis That Reveals All

The difference reveals itself most clearly in times of crisis. When systems break, when markets shift, when the unexpected arrives—these moments demand leaders who can cut through complexity with precision. They ask the questions that matter because they know what matters, because they’ve seen how similar situations unfolded before. They move with speed not because they’re reckless, but because they recognize patterns from their climb through the organization.

Yet in our rush to scale, particularly visible in the frenetic world of startups, we repeatedly make a costly mistake. We promote too quickly, we parachute in leaders from different domains, we assume that generic management skills transfer seamlessly across contexts. And so we get managers who cannot distinguish between a junior developer’s legitimate struggle and an excuse. We get leaders who, lacking the depth to ask penetrating questions, settle for marking problems and performing leadership rather than solving what’s actually broken.

The damage spreads quietly at first. Teams begin working on the wrong priorities because leadership cannot ask the questions that would reveal misalignment. Talented people grow frustrated as their expertise goes unrecognized. The organization develops a strange quality where everyone is busy but little improves. And most insidious of all, the culture shifts—away from solving root causes toward managing optics, away from accountability toward theater.

What Actually Drives Great Leaders

What drives the exceptional leader, the one who asks the right questions and sees through to root causes? It cannot be merely ambition—the charlatan possesses that in abundance. It must be something deeper: a genuine commitment to organizational betterment. Not personal glory. Not résumé building. But rather an almost craftsman-like dedication to fixing what’s actually broken, to unlocking the potential trapped within underperforming systems, to creating conditions where others can excel.

This motivation manifests quietly, less theatrically than we might expect. Such leaders demonstrate their commitment through digging deep, through their patience in understanding complexity, through their willingness to make unpopular decisions that serve long-term health over short-term optics. They measure themselves not by how impressive they appear but by whether the organization functions more effectively because of their presence.

This orientation toward genuine betterment cannot be faked indefinitely. It reveals itself in a hundred small ways—in which details the leader attends to, in how they react when challenged, in whether they surround themselves with capable people or comfortable yes-men, and critically, in whether their questions reveal deep familiarity with the domain or merely surface-level engagement.

What This Means for You

If you hire or promote leaders: Look for those who’ve climbed through complexity in your domain or similar ones. Present them with a real organizational problem and watch what they ask—do their questions reveal pattern recognition from experience, or are they generic inquiries anyone might pose? Examine their motivation: do they speak of the organization’s betterment or their own trajectory?

When you find leaders who ask penetrating questions born from experience, who’ve earned their understanding through the climb, who orient toward genuine problem-solving—empower them. Place them in positions of real authority. Remove the obstacles that prevent their effectiveness.

And when you identify the opposite—the polished performers who ask shallow questions because they lack the experience to know what truly matters, the ones who care more for appearance than substance—remove them. Swiftly. Their presence actively damages the organization by promoting superficial thinking and rewarding theater over substance.

If you’re developing yourself: Resist the shortcut. Build your understanding from the foundation upward. Seek positions where you’ll encounter real complexity, where you’ll have to think through problems without clear precedent, where failure has genuine consequences. This is how you develop the ability to ask questions that matter—not by studying leadership theory, but by accumulating the pattern recognition that only comes from direct experience.

Pay attention to the moments when your questions miss the mark or when someone with more experience asks something you hadn’t considered—these are learning opportunities showing you what patterns you haven’t yet internalized. Accept that this wisdom comes slowly, through accumulated experience across thousands of small decisions and their consequences.

And most importantly, check your motivation regularly. Are you pursuing leadership to be seen as a leader, or to actually improve the systems and people you’d be entrusted with? This distinction determines every decision you’ll make, every priority you’ll set, every question you’ll ask or fail to ask.

The Long Path Worth Taking

The path to becoming a leader worth following is longer and humbler than our culture often acknowledges. It requires climbing through complexity before presuming to direct it. It demands learning to see what matters—developing the experiential wisdom to know which questions reveal truth—before claiming to know what should be done.

Napoleon understood this. Even as Emperor, he could be found aiming the cannons himself during battles. He knew that leadership divorced from this kind of experiential understanding is mere performance. And performance, when lives and empires hang in the balance, is catastrophically insufficient.

The organizations that thrive—whether businesses, public institutions, or nations—are those led by people who climbed before they commanded, who developed the wisdom to ask penetrating questions before they presumed to have answers, who solve rather than perform. Everything else is theater, and theater, sooner or later, collapses under the weight of unresolved problems it was too superficial to even properly question.