When Certainty Doesn’t Come

Introduction

In When Expertise Isn’t the Answer, I argued that technical expertise is remarkably well suited to recognizing established solutions. Leadership, however, increasingly asks us to solve problems for which no established solution exists—not by abandoning expertise, but by extending disciplined expertise beyond the limits of pattern recognition.

That naturally raises another question.

If accomplished professionals are exceptionally good at solving difficult problems, why do so many struggle with leadership?

We can toss out the usual bromides: fear, incompetence, or the vaguery that someone “isn’t cut out for leadership.”

The more interesting answer is that they are often behaving exactly as they were trained.

Think about how most technical professions develop expertise. Whether we are physicians, engineers, military officers, software developers, or researchers, our education rewards disciplined observation, careful analysis, and increasingly accurate judgment. We learn to gather better information, distinguish signal from noise, challenge assumptions, and reduce uncertainty before acting. As experience accumulates, our confidence grows—not because we become more comfortable guessing, but because we become more adept at recognizing what we have already learned to recognize.

That educational system (as I’ve alluded to in prior posts) is designed to produce exactly what it produces—and thank goodness.

Technical experts require precisely that level of discipline. Imprecision and lack of expertise do not pair well with dosing medications or launching rockets.

The difficulty is that leadership eventually presents problems that refuse to cooperate with even the most expert ability to recognize.

There may be no established best practice. No guideline. No randomized trial. No experienced colleague who has already solved this exact problem. Additional analysis may improve our understanding of the situation, but eventually it stops producing something many technical professionals have spent their entire careers expecting:

Certainty.

Without that familiar certainty, those unaccustomed to leadership roles may fall into a few stereotypical traps..

Some endlessly dissect the problem without ever proposing a solution—even a strawman to refine or pilot. We call this analysis paralysis.

Others repeatedly discuss a proposed solution at meeting after meeting without implementation. That becomes planning to plan.

Still others avoid tackling the problem altogether because, although the status quo is far from optimal (or even terribly function), it’s not catastrophically broken. If it ain’t broke…

The irony is almost painful.

The habits that made us exceptionally effective within our technical disciplines can become the very habits that prevent us from moving forward as leaders. Not because those habits are wrong, but because they were developed for a different category of problems.

Leadership eventually asks something our professional training rarely emphasizes.

Not:

Can you recognize the right answer?

But:

Can you responsibly move an organization forward when no one can honestly promise the answer is right?

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When Expertise Waits

Technical professions reward a very particular relationship with uncertainty.

When we encounter something we do not understand, we are taught to gather more information. If the diagnosis is unclear, order another test. If the engineering analysis is incomplete, collect more data. If research findings conflict, run another experiment. If intelligence is uncertain, conduct additional reconnaissance.

Don’t guess, gather better information, if it exists.

Our patients deserve physicians who do not stop thinking too soon. Bridges deserve engineers who do not ignore inconvenient calculations. Scientific progress depends on researchers who challenge their own conclusions before anyone else has the opportunity.

Reducing uncertainty before acting is one of the defining characteristics of technical excellence.

So what is different about leadership, and where does the discomfort for technical experts arise?

Imagine an organization considering a major restructuring. Every department can make a compelling argument for preserving the current structure. Every proposal carries potential benefits and unintended consequences. No randomized trial, no clinical practice guideline, no engineering handbook, and no systematic review for your specific institution.

You can certainly gather more information, seek perspectives from people who disagree with you, identify assumptions, challenge your own biases, and explore second- and third-order consequences.

The limit of this becomes reveals an uncomfortable reality: eventually the additional information stops changing the decision.

That moment is surprisingly difficult for many accomplished professionals because our intuition tells us that if we simply think harder, read one more paper, consult one more expert, or hold one more meeting, certainty will finally arrive.

Many organizations become mired in these traps while masquerading as productive. Meetings generate additional meetings. Working groups create subcommittees. Strategic planning becomes planning a strategic planning retreat to discuss…wait for it

…strategy.

Calendars stay full. Everyone appears busy. Thoughtful discussion continues.

No action though; plans remain plans.

The phrases analysis paralysis, planning to plan, and if it ain’t broke are often spoken with a hint of sarcasm. Beneath the humor, however, lies something worth understanding.

These failures are rarely the result of laziness or indifference. Some observers invoke Hanlon’s Razor and attribute them to stupidity rather than malice.

I propose that a better lens to view these quagmires is “expertise behaving like experts not leaders.”  The obstacle is no longer a lack of intelligence, experience, or diligence. Experts have those in spades

The developmental challenge is recognizing the moment when disciplined analysis has done its job—and disciplined action must begin.

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The Cost of Waiting

What underlies those three familiar failure modes?

Technical experts who have spent decades making high-stakes decisions often develop an understandable expectation that implementation should wait until the solution is nearly perfect.

There are decisions that deserve another day of analysis, another conversation, or another expert opinion. Acting prematurely can be every bit as irresponsible as acting carelessly. Good leaders are not rewarded for impulsiveness any more than good physicians are rewarded for ordering unnecessary procedures simply to appear decisive.

If you’ve ever watched footage of the Tacoma Narrows Bridge collapsing, you’ll understand the image that haunts civil engineers. If you’ve studied the Libby Zion case from a clinician’s perspective, you’ll recognize one of the roots of defensive medicine.

The challenge is recognizing when the nature of the problem changes.

At some point, uncertainty stops being something that can be eliminated and becomes something that must be managed.

At some point failure must be accepted as a likelihood, and aversion to risk must be tamed with vision of possibility. 

That transition is uncomfortable because it violates one of the deepest assumptions of technical training:

That somewhere there is one best answer.

Leadership teaches a different lesson.

Some organizational problems are waiting for commitment, not discovery.

This is also where accomplished professionals can swing too far in the opposite direction.

“Good enough. Let’s just pick something.”

While that response wears the costume of decisiveness, underneath it is impatience masquerading as leadership. Lowering standards is as problematic as refusing to act.

One extreme mistakes caution for wisdom while the other mistakes motion for progress.

Leadership requires identifying the best responsible action available under the conditions that actually exist, and recognizing that doing nothing also carries consequences.

We’ve discussed in this blog (repeatedly) that reality is undefeated. Reality is remarkably indifferent to our desire for certainty.

Organizations move forward whether leaders choose a direction or not.

Organizations move forward whether leaders choose a direction or not. Thanks to Neil Peart we have great song lyrics to pin on these potential errors of omission: 

If you choose not to decide, you still have made a choice. 

[insert  awesome drum fill here]

Leaders still exercise discipline, gather evidence, seek disagreement rather than affirmation, identify assumptions, explain their reasoning, and remain intellectually humble enough to change course when reality teaches them something new.

That last point deserves emphasis. Changing course is not evidence that the original decision was irresponsible. Failure is information. Responding intelligently to failure is often evidence that the organization is learning.

I don’t mean lowering the bar.

Perfection remains the target, excellence remains the standard.

Accepting reality simply means recognizing that moving toward perfection through excellence requires time and distance traveled.

Every organizational decision generates new information; some of it confirms our reasoning. challenges assumptions, or reveals unanticipated consequences. Good leaders treat all of it as data that improves the next decision rather than as a referendum on whether the previous one should have been made.

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Growth Mindset and Learning Organizations

One of the most influential ideas in educational psychology over the past several decades has been Carol Dweck’s work describing fixed and growth mindsets. In its simplest form, a fixed mindset views ability as largely static, while a growth mindset views it as something that can be developed through effort, feedback, and deliberate practice.

That concept is fundamentally describing individuals.

What happens when we apply the same concept to organizations?

Does an organization treat mistakes primarily as signs of immutable weakness, or as opportunities to improve? 

Let’s call it a Learning Organization.

That raises another question.

This begs the question of how growth mindset folks, and fixed mindset folks experience being in a Learning Organization vs a Non-Learning Organization.  

Ooooh, I feel a 2×2 table coming.

	Learning Organization	Non-Learning Organization
Growth Mindset Individuals	Highest organizational capacity. Individuals continue developing while the organization captures and amplifies what they learn.	Frustrated innovators. People improve themselves, but their learning rarely changes the system. Eventually many leave.
Fixed Mindset Individuals	The system partially compensates. Organizational routines continue generating improvement even when some individuals resist developmental feedback.	Organizational brittleness. Neither people nor the institution reliably improve, and capability slowly erodes over time.

Every quadrant exists.

Most of us have worked in at least two of them.

Notice what this matrix does not say.

It does not suggest that individual growth mindset and organizational learning are identical, but rather they interact to amplify, or mitigate one another.

Growth-oriented professionals make learning organizations stronger.

Learning organizations make it easier for professionals to remain growth-oriented.

The reverse is equally true.

Brittle organizations do not simply fail to develop people. They become remarkably effective at driving away the very individuals most capable of improving them.

From this emerges another leadership responsibility:

Development.

And there are two flavors of development.

Organizational development, where leaders create an environment in which uncertainty generates learning rather than paralysis.

Individual development, where leaders help team members become increasingly capable of learning from uncertainty themselves.

I hope, as a reader of this blog, that last responsibility sounds familiar.

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Leadership and Mentorship

Leadership and mentorship are often discussed as though they were interchangeable.

Mentorship is fundamentally about developing people so they can function after the mentor is gone.

Leadership is fundamentally about developing the culture through which people can continue progressing the organization after the leader is gone.

There’s a distinction in roles even if same individual often occupies both.

A department chair mentors junior faculty while simultaneously leading the department.

A military commander develops subordinate officers while building an organization capable of succeeding after that commander rotates elsewhere.

Mentor: How do I help this individual become more capable?

Leader: How do I help this organization become more capable?

Both questions matter because organizations do not become exceptional simply by hiring exceptional people.

Collective expertise does not magically become organizational capability.

If it did, every hospital filled with brilliant physicians would automatically become an outstanding institution. Every multidisciplinary committee would consistently outperform the individuals sitting around the table. Every technology company full of experts would naturally evolve into a billion-dollar unicorn that continuously learns and adapts.

If you were the person who loathed group projects throughout your training, you already know that teams do not become capable by osmosis.

Someone has to intentionally create the conditions under which organizational learning occurs.

Mentorship helps individuals develop the habits uncertainty demands: intellectual humility, curiosity, resilience, and the confidence to act responsibly without demanding impossible certainty.

Good mentors do more than answer questions.  They help people become increasingly capable of asking better ones.

Leadership scales those individual gains by facilitating their best use within a team.

A learning organization captures what individuals discover, spreads those lessons beyond a single team or department, and embeds them into the culture so the next person begins farther ahead than the last.

Mentorship and leadership are not competing responsibilities for development; They are both necessary, neither sufficient alone.

A brilliant mentor working inside a brittle organization may develop outstanding people only to watch them become frustrated when their ideas repeatedly collide with a culture unwilling to learn.  Conversely, an organization may establish excellent systems for continuous improvement, but without leaders willing to invest personally in developing people, those systems gradually lose the curiosity, creativity, and judgment that give them life.

Experts improve the work.

Mentors improve the people doing the work.

Leaders create the conditions in which both continue improving together.

That is how expertise becomes organizational capability.

Not simply within an individual.

Across an entire organization.

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The Leadership Pipeline

Brittle organizations create an insidious feedback loop, making them more brittle.

Organizations readily notice when a department chief retires unexpectedly or an experienced executive accepts a position elsewhere.

Far less visible is the attrition of talented people deciding they never want those positions in the first place, and  disappearing quietly into the background.

Talented people decide they never want those positions in the first place.

A gifted physician watches the same story play out over and over:

• Respected leaders become increasingly consumed by bureaucracy rather than development.
• Innovative colleagues are punished for thoughtful risks that fail.
• Difficult questions become unwelcome when the answers are inconvenient.
• Advancement appears to require protecting the status quo rather than improving it.

What does a growth-oriented professional conclude?

That growth itself is desirable, but not here.

Some remain outstanding clinicians while quietly abandoning any aspiration toward leadership. Others simply leave.

Many, by example, inspire their protégés and collaborators, to leave with them. People naturally gravitate toward environments where development is encouraged rather than merely tolerated.

The result is a slow depletion of organizational capability.

For a while, the day-to-day mission continues, and the organization appears functional.

Then, years later, the succession plan quietly collapses, or conditions thought static unexpectedly change.

The experienced candidates who once would have competed for leadership positions, or innovated to adapt to those changing conditions are simply no longer there.

What looks sudden is often the delayed consequence of years spent consuming leadership capacity faster than creating it.

Leadership is often evaluated (rightly) by asking whether today’s mission succeeded.

Necessary but not sufficient. We must also ask:

Is the organization becoming more capable because of today’s leadership, or merely surviving until tomorrow?