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Making Decisions is as Easy as Pie

Written by Jack Briggs on . Tagged with Higher Education, Crises.

Nothing is ever as good as you dream it, nor as bad as you imagine it.

I’m a major-league catastrophizer. Just ask my wife. My default is to run through the absolute worst-case scenario and consider all the ways a situation could go wrong. I tell myself it’s “just being prepared,” but honestly, it’s rarely helpful. The worst-case scenario I envision never actually happens, and meanwhile, I’ve stressed myself (and everyone around me) to exhaustion.

You might lean the other way as the optimist who envisions the perfect outcome. I do this too: picturing the ideal relationship, the flawless vacation, the dream job, or the ideal project. But in the real world, nothing is perfect. Chasing perfection wastes energy and drains resources, leaving you frustrated and your organization overextended.

The Leadership Illusion: Easy Decisions

One of the most unrealistic dreams leaders have is that difficult decisions will somehow be easy. We crave a clear choice with a guaranteed best outcome. We want to dodge the “bad call” with the terrible results we imagine.

But real leadership, especially in a crisis, demands that we train ourselves to neither daydream about perfection nor spiral into catastrophe. In a high-functioning organization, all the easy calls have already been made long before the decision lands on your desk. What’s left?

The least-worst option.

Your job as a leader in that moment is simple but daunting:
Say YES or NO to the least-worst option — and then own it.


Why Is This So Hard?

We fixate on imagined outcomes.
But here’s the truth: you don’t control outcomes.

Between your decision and the final result, countless variables intervene:

  • Luck
  • Weather
  • Other people’s actions
  • Bad or incomplete information at the time of choice

All of these can derail or elevate your outcome, and you can’t control them.


So, What Can You Do?

Stop measuring your current decision against some imaginary future, whether it’s a disaster or a dream.

Instead, put all your energy into making the best decision you can right now, using:

  • Principles – Ground yourself in your organization’s core values.
  • Humility – Bring other perspectives into the mix.
  • Decisiveness – Commit when it’s time to act.

Pie Chart

The Pie Chart Approach to Decision-Making

Picture a pie chart.
Before you make your first decision, you have the entire pie with an infinite range of possible futures.

Make that first decision guided by principles, humility, and decisiveness, and the “universe of outcomes” instantly shrinks to a smaller slice. Each subsequent good decision compounds this effect, narrowing the spectrum of possible futures to an ever-smaller, more acceptable range.

Over time, your slice of “acceptable outcomes” gets more focused, and the likelihood of a good outcome improves.


Henry Kissinger once said:

“Statesmen are not called upon only to settle easy questions. These often settle themselves. It is where the balance quivers, and the proportions are veiled in mist, that the opportunity for world-saving decisions presents itself.”

Leadership isn’t about waiting for clear skies. It’s about stepping into the mist, slicing the pie one decision at a time, and owning the call.

Jack Briggs, portrait
Equip Your Team With a Proven Framework
A career spent making life-or-death decisions in combat and high-stakes environments has taught me one truth: when a crisis hits, hesitation is a liability. I help senior leaders turn a moment of chaos into a testament to their leadership.