Calibrating Courage - A Corollary to “Almost Beautiful”

by Mitch Sowards, #AIEditor

In my previous article, Almost Beautiful, I suggested that leaders should learn to distinguish between careless mistakes and what I called Almost Beautiful mistakes—worthy attempts that narrowly miss excellence. Those are the kinds of mistakes that often accompany intelligent risk-taking, creative thinking, and the pursuit of something genuinely difficult. And that in a competitive world, the margin by which you (or your team) make fewer “almost beautiful” misses than your competitors is the margin by which one of you wins in the marketplace.

Some readers responded with a thoughtful follow-up question.

"That makes sense... but surely we shouldn't encourage people to swing for the fences all the time?"

Exactly.

In fact, I believe the healthiest organizations do something much more nuanced.

They don't simply encourage courage.

They calibrate it.

Empowerment Isn't Enough

Recently I was mentoring a newly appointed CEO. One of his primary goals was to build a more empowered organization—one where people would make thoughtful decisions without constantly seeking permission from leadership.

It's an admirable goal.

But as we talked, he wrestled with a practical concern.

"How exactly does one build an empowered team?"

Or put differently:

"How do they know when to be brave and move ahead and when not to?"

That question took me back to an earlier employer whose culture had an exceptionally strong bias toward action. The CEO's philosophy was straightforward:

If your proposed course of action has at least a 50 percent chance of succeeding, take it.

Personally, I always felt that threshold was a bit too adventurous—essentially a coin flip. But that wasn't really the point.

The point was that everyone understood the expectation.

People weren't guessing how much risk leadership wanted them to assume. They had been given a clear decision standard.

I told my CEO mentee that whatever threshold he ultimately chose was less important than making sure his team understood it, trusted it, and knew they would be evaluated against it rather than judged solely by outcomes.

That coaching conversation led me to an important realization.

Empowerment without guidance isn't really empowerment. It's abandonment.

If leaders want people to exercise good judgment, they must first communicate what good judgment looks like in their organization.

Great Organizations Calibrate Courage

Every organization has an appetite for risk, whether it has been articulated or not.

Some organizations compete on speed. They value rapid action, quick decisions, and the willingness to recover from occasional mistakes.

Others operate in environments where safety, precision, compliance, or reputation carry such significant weight that caution is the wiser strategy.

Neither approach is inherently superior.

The danger is leaving every employee to invent their own threshold.

One leader may expect people to move forward when they're 70 percent confident.  Another may expect 90 percent confidence before acting.  Those aren't merely operational preferences. They're cultural expectations.

Leaders should communicate those thresholds explicitly.

Then, when evaluating outcomes, they should ask not only:

"Did it work?"

But also:

"Did they operate within the decision framework we asked them to use?"

That's a much fairer—and ultimately much more developmental—question.

Courage Requires Judgment Twice

The more I reflected on this, the more I realized that courage isn't calibrated only once. I’ve come to believe that leaders calibrate courage at two distinct moments.

First: Before the Decision

This is the moment when someone stands at the fork in the road.

Should we proceed?

Should we wait?

Should we gather more evidence?

Should we ask for help?

Should we stop?

Good leaders don't simply tell people to "use good judgment."

They help define what good judgment looks like.

Perhaps your organization values speed over perfection. Perhaps protecting customer trust outweighs moving quickly. Perhaps significant financial decisions always require broader consultation.

Whatever your philosophy, don't leave it unspoken.

People cannot consistently honor expectations that have never been clearly articulated.

And whenever decisions involve meaningful financial, organizational, or emotional consequences, they deserve more than intuition alone. Gather evidence. Invite differing viewpoints. Follow a disciplined decision-making process. Good judgment is rarely accidental.

Second: During Execution

Even after a decision has been made, courage must continue to be calibrated.

This lesson has been reinforced countless times on the racquetball court.

Suppose you've attempted three difficult kill shots in a row.  Each one was almost perfect. Each one missed by just enough to cost you the point.

What should you do next?

Many players stubbornly attempt a fourth spectacular shot.

Experienced players often do something different.

They make a solid, disciplined return.

They stay in the rally.

They allow themselves to regain rhythm before attempting another difficult shot.

The goal hasn't changed. Winning still requires beautiful shots.

But wisdom recognizes that timing matters.

Sometimes the courageous decision is to attempt something extraordinary.

Sometimes the courageous decision is simply to execute the fundamentals exceptionally well.

Not Every Situation Calls for Maximum Boldness

There are moments when caution deserves greater weight.

If a mistake could jeopardize client trust, public safety, significant financial resources, or an organization's reputation, slowing down is often wise.

Double-check. Invite another set of eyes. Take the extra hour.

Likewise, if recent execution has been unusually poor, it may be time to rebuild confidence through consistently excellent fundamentals before attempting increasingly difficult challenges.

Athletes understand this instinctively.

Sometimes you don't need a highlight-reel shot.

You simply need to stay in the game.

Organizations are no different.

The Leader's Responsibility

One of the most important responsibilities of leadership is not simply encouraging courage.

It is calibrating it.

When leaders clearly communicate how much initiative they expect...

how much evidence they require...

how much risk they consider appropriate...

and how they will evaluate decisions...

they remove uncertainty that otherwise causes capable people either to freeze or to act recklessly.

Empowered organizations are not built by telling people to "figure it out."

They are built by teaching people how brave to be.

One Final Thought

In Almost Beautiful, I argued that organizations should not punish every worthy attempt that falls just short of excellence.

I still believe that.

But there is an equally important companion principle.

Great performers know when to attempt difficult things—and when not to.

Great leaders help everyone else learn that distinction too.  Perhaps that’s what empowerment really is—not deciding for people, but teaching them how to decide well.

Because in the end, courage isn't measured by how often we take risks.

It's measured by how wisely we choose them.