Leading When You Don’t Have All the Answers

The Luxury of Hindsight

I recently came across a quote from Duke Basketball Head Coach Jon Scheyer that I've found myself thinking about quite a bit.

"The hardest part of being a leader is making real time decisions with imperfect or insufficient information."

It's one of those statements that seems fairly obvious when you first read it.

Of course leaders have to make difficult decisions.

Of course they don't always have all the information.

That's part of the job, right?

But the longer I sat with it, the more I began appreciating just how much complexity is hiding inside those few words.

Because there's something profoundly uncomfortable about being responsible for a decision when you don't have enough information to know whether you're making the right one.

And there's something even more uncomfortable about knowing that other people may be affected by whatever you decide.

I've spent years studying leadership, building teams, and trying to understand what separates people who simply occupy leadership positions from those who genuinely make a difference.

And one thing has become increasingly apparent.

Leadership is remarkably easy to evaluate in hindsight and extraordinarily difficult to practice in the moment.

Think about it.

After something goes wrong, everyone suddenly seems to know what should have happened.

The warning signs were obvious.

The alternative was clearly better.

The risks should have been anticipated.

The decision never should have been made.

But were those things actually obvious when the decision was required?

Or have we simply gained the luxury of information that wasn't available to the person making it?

I think that distinction deserves far more attention than we typically give it.

Everyone Has a Plan Until the Game Starts

I find sports to be a fascinating illustration of leadership because decisions and consequences are so visible.

Imagine being a basketball coach with two minutes remaining in a close game.

Your team is exhausted.

One of your best players is struggling.

The opposing team has adjusted its defensive strategy.

You've noticed something that might create an opportunity, but you aren't entirely certain how the other coach will respond.

Do you call a timeout?

Change the lineup?

Adjust the offense?

Trust the players to figure it out?

Every option carries potential consequences.

And perhaps most importantly, the game isn't going to stop indefinitely while you evaluate them.

You have to make a decision.

Now.

From the comfort of our couches, we get to analyze those decisions with the benefit of instant replays, multiple camera angles, statistical breakdowns, and commentators explaining what should have happened.

The coach has none of those luxuries in quite the same way.

They have experience.

Preparation.

Instinct.

The people around them.

And whatever information they can process before the next moment demands their attention.

That's what makes Scheyer's observation so compelling.

The difficulty isn't simply making a decision. It's accepting responsibility for an outcome you cannot fully predict.

And while the consequences of a basketball game and the consequences of organizational leadership can be very different, the underlying challenge is remarkably similar.

The Myth of the Perfect Decision

I think many of us have been conditioned to believe that good decision-making should produce good outcomes.

And generally speaking, there's some truth to that.

We gather information, evaluate alternatives, assess risks, and choose what appears to be the most reasonable path forward.

If we're thoughtful enough, experienced enough, and analytical enough, we should be able to make the right decision.

Right?

Well, not necessarily.

Because a good decision can produce a bad outcome.

And a bad decision can occasionally produce a good one.

Suppose a leader is responsible for deciding whether a software product is ready to be released.

The team has completed its testing.

The known defects have been reviewed.

The engineers are confident in the changes.

The business has communicated a clear deadline.

Based on the information available, releasing the product appears reasonable.

So the leader makes the decision to proceed.

And something breaks.

A dependency behaves unexpectedly.

An edge case nobody anticipated emerges.

A problem that wasn't visible in testing becomes apparent in production.

Suddenly, everyone wants to know why the release was approved.

It's a fair question.

But I think there's a more useful question hiding beneath it.

Was the decision unreasonable based on what was known at the time, or did the outcome reveal something that couldn't reasonably have been anticipated?

Those are two very different situations.

One might indicate poor judgment, inadequate preparation, or unnecessary risk-taking.

The other might simply reflect the reality of operating within a complex system.

We should absolutely examine decisions that produce unfavorable outcomes.

We should learn from mistakes.

We should challenge our assumptions and improve our processes.

But I think we do ourselves a disservice when we assume that an unfavorable outcome automatically proves the decision was wrong.

Because if we evaluate every decision exclusively by its outcome, we may unintentionally teach people that the safest approach is to avoid making decisions altogether.

And that creates an entirely different problem.

Indecision Is Still a Decision

Something I've come to appreciate about leadership is that choosing not to act rarely means choosing nothing.

It often means accepting whatever happens while we're waiting.

And sometimes that cost is greater than we realize.

Imagine a team struggling with an organizational problem.

Responsibilities are unclear.

Priorities are competing.

People are frustrated.

Everyone recognizes that something needs to change.

But the leader wants more information before making a decision.

Another meeting is scheduled.

Additional feedback is requested.

A working group is established.

Someone suggests gathering more data.

None of those activities is inherently wrong.

In fact, they might be entirely appropriate.

But at some point, the pursuit of certainty can become a convenient disguise for avoiding responsibility.

Because as long as we're still gathering information, we haven't technically made the wrong decision.

We also haven't necessarily made anything better.

Meanwhile, the people experiencing the problem continue carrying its consequences.

I've come to believe that the cost of indecision deserves the same scrutiny as the risk of making the wrong decision.

That doesn't mean we should rush into every situation.

Some decisions require deliberate analysis.

Some carry consequences that are difficult or impossible to reverse.

And in situations involving safety, ethics, or significant risk to others, slowing down may be the most responsible thing we can do.

But not every decision deserves the same amount of deliberation.

Sometimes we need to recognize that we have enough information to take a reasonable next step, even if we don't have enough information to predict the final outcome.

The challenge is developing the judgment to know the difference.

Leadership Is Not a Test of How Much You Know

This particular aspect of Scheyer's quote resonates with me because my own leadership journey hasn't followed the traditional path many people expect.

As someone who manages software engineers without having spent years working professionally as a developer, I've had to become comfortable making decisions in environments where the people around me possess expertise I don't.

That can be intimidating.

There's an enormous difference between understanding a technical concept and having years of practical experience applying it.

And I have too much respect for the people I work with to pretend otherwise.

But I've learned something important.

I don't necessarily have to possess the most technical knowledge to contribute meaningfully to a difficult decision.

I do, however, need to understand how to bring the right knowledge into the conversation.

Who has experience with this problem?

What assumptions are we making?

What risks haven't we considered?

What does the team believe?

Where do we have genuine disagreement?

And perhaps most importantly, what happens if we're wrong?

Those questions don't eliminate uncertainty.

But they can make the uncertainty more visible.

And making uncertainty visible is valuable.

Because there's a difference between making a decision without all the answers and making a decision without understanding what you don't know.

I also think this is where servant leadership is frequently misunderstood.

Being a servant leader doesn't mean avoiding difficult decisions or simply agreeing with whatever the team recommends.

It means recognizing that leadership exists to serve a purpose greater than the authority of the person holding the title.

Sometimes serving the team means giving them autonomy.

Sometimes it means asking questions.

Sometimes it means removing an obstacle.

And sometimes it means making a difficult decision that people may not agree with, while accepting responsibility for the consequences.

You can trust the expertise of the people around you without surrendering your responsibility to exercise judgment.

In fact, I would argue that good leadership requires both.

We Should Spend Less Time Pretending to Be Certain

There's an interesting contradiction in how we often expect leaders to behave.

We want them to be confident.

Decisive.

Capable of providing direction.

But we also want them to be humble, curious, collaborative, and open to feedback.

Those expectations can feel contradictory.

How can someone be confident when they don't have all the information?

How can they be decisive while remaining open to the possibility that they're wrong?

I think the answer lies in understanding that confidence and certainty aren't the same thing.

Certainty says, "I know this is the right answer."

Confidence can say, "Based on what we know, I believe this is the best available path forward, and I'm prepared to adjust if we learn something different."

One leaves very little room for learning.

The other expects learning to be part of the process.

Personally, I have far more respect for a leader who's willing to acknowledge uncertainty than one who attempts to disguise it behind a carefully constructed appearance of authority.

Because people can usually recognize when someone is pretending to know more than they do.

And when that pretense becomes part of the culture, something dangerous begins to happen.

People stop admitting what they don't know.

They become reluctant to challenge assumptions.

They hesitate to raise concerns.

And eventually, the information the leader most desperately needs may become the very information people are least comfortable sharing.

Think about the irony of that.

A leader trying to project certainty can unintentionally create an environment that makes informed decision-making more difficult.

The appearance of confidence should never become more important than the pursuit of understanding.

I'd rather lead a team where someone feels comfortable saying, "I think we're missing something," than one where everyone nods in agreement because they're afraid of challenging the person in charge.

Even if it makes the decision more complicated.

Especially if it makes the decision more complicated.

The People Behind the Decision

There's another part of leadership that I don't think we discuss enough.

Decisions don't exist in isolation.

They affect people.

And sometimes those effects extend well beyond the organization.

Consider a decision to change a team's priorities.

On paper, it might seem relatively straightforward.

The business has identified a more valuable opportunity.

Resources need to be redirected.

The team needs to adjust.

But beneath that seemingly simple decision are people who have invested time, effort, and emotional energy into their work.

Someone might have spent months developing a feature that will no longer be completed.

Someone else might have been counting on an opportunity to demonstrate their capabilities.

Another person might already be struggling with the demands of their workload.

The decision may still be necessary.

It may even be the best decision available.

But that doesn't eliminate the responsibility to recognize its human consequences.

I've always believed that the people we work with are more than the roles they occupy.

They have lives outside of their professional responsibilities.

Families.

Aspirations.

Concerns.

Commitments.

And sometimes the decisions we make as leaders affect those things in ways we don't immediately recognize.

That's a responsibility I don't take lightly.

It also reinforces why I believe empathy and accountability are not opposing leadership qualities.

You can make a difficult decision while caring deeply about the people it affects.

You can explain why something needs to happen without pretending that explanation makes the consequences disappear.

And you can acknowledge that a decision may be disappointing while remaining confident that it was necessary.

Being accountable for a decision means more than accepting credit or blame. It means taking responsibility for how the decision affects the people who must live with it.

That might be one of the most important parts of leadership.

And one of the hardest.

The Goal Isn't to Eliminate Uncertainty. It's to Become Better at Navigating It.

The more I've thought about Scheyer's quote, the more I've come to believe that much of leadership development should focus less on finding perfect answers and more on improving how we make decisions when perfect answers aren't available.

Because uncertainty isn't going away.

Organizations are complex.

People are complicated.

Markets change.

Technology evolves.

Priorities shift.

And even with the most sophisticated tools available, there will always be circumstances where the information we need is incomplete, contradictory, or simply unavailable.

So what do we do?

We develop better judgment.

We learn to distinguish between decisions that can be easily reversed and those that require additional caution.

We build relationships with people whose perspectives challenge our assumptions.

We create environments where difficult information can travel freely.

We become comfortable asking questions.

We recognize when more information is genuinely valuable and when we're simply delaying the inevitable.

And we develop the humility to revisit a decision when reality teaches us something new.

Something I find particularly important is creating teams that don't view changing direction as an admission of failure.

Of course, constantly changing direction without good reason can be incredibly disruptive.

But adjusting a decision in response to new information is not inherently a weakness.

Sometimes it's precisely what responsible leadership requires.

The objective shouldn't be to defend yesterday's decision simply because we were the ones who made it.

It should be to make the best decision we can with what we know today.

Even when that means acknowledging that something we believed yesterday is no longer true.

That's not inconsistency.

That's learning.

The Difference Between Being Responsible and Being Right

I wonder how many leaders quietly carry the belief that their credibility depends on getting every important decision right.

I suspect it's more than we'd care to admit.

There's pressure associated with being the person others look to for direction.

Pressure to appear capable.

Pressure to justify the confidence others have placed in you.

Pressure to deliver outcomes that validate the decisions you've made.

And sometimes that pressure can make it difficult to separate our personal identity from the results of our decisions.

If the decision succeeds, we feel validated.

If it fails, we question ourselves.

But I think there's a healthier way to understand that responsibility.

Our obligation isn't to predict the future perfectly.

It's to approach decisions with the seriousness they deserve.

To prepare.

To listen.

To seek perspectives we may not naturally consider.

To be honest about uncertainty.

To act when action is necessary.

And to remain accountable when the outcome isn't what we expected.

That's what I want from the people who lead me.

And it's what I try to provide to the people who trust me to lead them.

Not perfection.

Not the illusion that every answer is available.

Just thoughtful judgment, genuine care, and a willingness to accept responsibility.

Being responsible for a decision doesn't mean you were guaranteed to be right. It means you were willing to own the decision when certainty wasn't available.

And I think there's a tremendous amount of courage in that.

Eventually, Someone Has to Make the Call

When I return to Scheyer's quote, I keep coming back to the image of a basketball coach standing on the sideline.

The clock is running.

The crowd is loud.

The players are looking for direction.

There are countless variables to consider, many of which cannot be fully understood in the time available.

The coach could spend the rest of the game analyzing possibilities.

But eventually, someone has to make the call.

Leadership works much the same way.

There will be moments when we have all the time and information we need to make a thoughtful decision.

We should appreciate those moments.

But there will also be times when the circumstances are changing faster than our ability to understand them.

When the available information is imperfect.

When people disagree.

When the risks are real.

When there isn't a clearly correct answer.

And when waiting for certainty may be just as consequential as choosing the wrong direction.

In those moments, I don't think leadership is about pretending the uncertainty doesn't exist.

It's about acknowledging it, understanding what matters most, and making the most responsible decision available.

Then doing something equally important.

Learning from what happens next.

Because perhaps the greatest difference between a good leader and a great one isn't how often they make the right decision.

It's how intentionally they approach decisions, how responsibly they handle the consequences, and how much better they become because of what they've learned.

I've never believed that leadership requires having every answer.

But I do believe it requires having the courage to act when the answers are incomplete, the humility to listen when others see something we don't, and the integrity to take responsibility when things don't turn out the way we'd hoped.

Maybe that's why Jon Scheyer's words resonate with me so much.

They capture a reality that every leader eventually encounters.

You don't get to wait until you know how the story ends before deciding what to do next.

You have to make a choice with the information available, knowing full well that the next chapter may reveal something you couldn't see before.

And when it does?

You learn.

You adjust.

You take care of the people affected.

And you keep leading.

Because leadership was never about knowing exactly what tomorrow would bring.

It's about being someone others can trust to help navigate whatever tomorrow brings, even when you don't have all the answers today.

One final thought: When evaluating a leader's decision, perhaps we should spend less time asking, "Did it work?" and a little more time asking, "Given what they knew at the time, was it a reasonable decision, and what did they do when they learned something new?"

I suspect we'd learn a great deal more about leadership by asking the second question.