“We herd sheep, we drive cattle, we lead people. Lead me, follow me, or get out of my way.” – George S. Patton

We were lost.

There was no other way to say it. Somehow, our convoy had deviated from the designated route, and we were driving through the non-descript night desert trying to find our way. Our vehicle operators were at the point of exhaustion, having driven for more than 24 hours straight and been awake at least another 12 hours longer than that. The choice seemed obvious enough: stop, rest, and recalibrate.

Except it wasn’t.

The decision chain that led to this moment was like something out of a bad sitcom. We didn’t give our operators sufficient rest time before leaving. We chose to depart without maps, relying on the only – now inoperative – digital navigation system in the organization. And we continued driving long after it was obvious that we were lost.

The commander struggled to make the decision to stop the convoy. Doing so wasn’t just an admission that we were lost; in his mind, it exposed him to criticism for every flawed decision that led to our current predicament. As he shouldered the weight of his previous decisions, he simply couldn’t make one more. What if he was wrong? What if the situation got worse? What if he got fired?

Better to drive on and hope for the best than risk facing the blunt – and inevitable – truth.

The Big Five

For many people, the decision space is not always a comfortable place. Even among the most senior leaders, the emotional discomfort associated with uncertainty can be difficult to manage. When someone suffers from imposter syndrome – the inescapable fear that they’ll be revealed as less capable than they appear – that discomfort grows exponentially worse.

Coping with the discomfort of uncertainty is essential to effective decision-making. The key is to condition the brain to focus on approach emotions (excitement) instead of avoidance emotions (doubt and anxiety), which helps to signal opportunity rather than adversity. In turn, this allows someone to more clearly view risk as a catalyst for opportunity instead of a shadowy threat.

In a recent MIT Sloan Management Review article, David Tuckett summarized his research into uncertainty and decision-making, noting that “effective decision makers share five key attributes that emotionally equip them to overcome the decision paralysis caused by doubt and anxiety — and enable them to undertake effective action when faced with uncertainty.”

  1. Positive view of change: Change is inevitable. It is far better to lead change than watch it go by.
  2. Reframing challenges as opportunities: There’s a silver lining in every cloud. Sometimes, it just takes a while to find it.
  3. Tolerance for uncertainty: When time to make a decision arrives, you’re never going to know everything you need to know. And that’s okay.
  4. Comfort with failure: Challenges and setbacks are just “opportunities to excel.” Or, as Wayne Gretzky used to say, “You miss 100% of the shots you don’t take.”
  5. Grounded optimism: Tuckett emphasized that the most crucial trait was the belief that outcomes will be positive even when plans go sideways. That perpetual optimism is what separates the best leaders from everyone else.

Tuckett’s findings challenge conventional thinking about decision-making in the midst of uncertainty. While most models foster and even encourage gathering more information for decision-making during uncertain times, Tuckett advocates creating a culture of what the military calls mission command: empowering your teams to accept risk and take the initiative despite incomplete information.

Once More Unto the Breach

Developing such a culture necessitates a depth of trust that often doesn’t exist in organizations. A 2024 Gallup poll revealed that only one in five employees had a strong sense of trust in their leadership and only one in four actually felt as if their leadership engaged them in any meaningful way. When viewed through the lens of Tuckett’s research, it’s not difficult to understand why managing uncertainty – and making decisions during uncertain times – is such a rare skill. Many leaders simply aren’t able to cultivate the culture of trust necessary.

But if a leader successfully forges those bonds of trust and seizes the mindset advocated by Tuckett, making the leap into uncertain waters still presents some very unique challenges. In a recent Forbes article, Jodie Cook, the founder of Coachvox AI, writes, “The biggest moments come with zero guarantees. Most people wait for certainty that never arrives.” In her opinion, overcoming analysis paralysis comes down to five key leadership traits:

1. Jump off the cliff.

“Top performers know that action beats analysis.” Don’t overthink the situation. Don’t wait for perfect data that isn’t coming. Take the leap and know that you’ll land on your feet.

2. Burn the boats.

Commit to the path forward. Don’t look back. Leave the past behind. The path ahead might be bumpy, but push onward and navigate it with confidence.

3. Follow principles over emotion.

Align your decisions with your values, not your feelings. Don’t debate decisions you already made or obsess over “what ifs.” Save your energy for what matters: the decisions you still have to make.

4. Choose speed over perfection.

No plan survives first contact with the enemy. Better to make a decision in the moment knowing you can navigate the path forward than to wait for perfect information.

5. Trust expensive lessons.

Vicarious learning – drawing on the expensive lessons others have paid – will help you to maneuver the uncertainty ahead. Internalize those lessons and use them to advantage.

Whatever happened to that lost convoy? Well, eventually we stopped. People rested. We ate. Someone who had kept their maps from a previous deployment laid them out over the hood of a HMMWV, determined our location, and got us on the right path. By morning we were back on the right road and arrived at our objective without further delay.

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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a co-founder and emeritus board member of the Military Writers Guild; the co-founder of the national security blog, Divergent Options; a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal; a member of the editorial advisory panel of Military Strategy Magazine; and an emeritus senior fellow at the Modern War Institute at West Point. He is the author, co-author, or editor of several books and is a prolific military cartoonist.