Are You Overthinking This?

The Decision-Making Trap That’s Slowing You Down

The Leadership Skill That Separates the Best from the Rest

Decision-making is one of the most critical leadership skills—but also where many leaders get stuck. Overthinking, hesitation, and endless analysis stall momentum and let opportunities slip away.

But here’s the secret: The best leaders don’t make perfect decisions. They make effective ones—quickly, confidently, and in a way that empowers their teams.

Don’t Be the Easy Button

When my team asks for help making a decision, my instinct isn’t to hand them the answer. Instead, I take a Socratic approach, asking open-ended questions that guide their thinking.

Most of the time, they already know the right move—they just need the confidence to act. If they hesitate, it’s usually because they fear making a mistake. That’s when I remind them of two things:

1️⃣ I trust their expertise and judgment.
2️⃣ No decision is failure-proof, but mistakes are learning opportunities—not punishable offenses.

I also make it clear that I’ll take ownership of the outcome. This creates a culture of psychological safety, where people feel empowered to act instead of waiting for direction.

Detach to See the Right Answer

A concept I learned from Jocko Willink is detachment—stepping back to see the bigger picture when stress clouds your judgment.

When you feel overwhelmed, pause. Breathe. Shift your perspective. Encourage your team to do the same. Sometimes, the right solution is obvious—you just need to step back to see it.

The OODA Loop: The Cure for Overthinking

The best decision-makers don’t get stuck in analysis paralysis. Instead, they follow a repeatable framework. One of my favorites is the OODA Loop, developed by Colonel John Boyd for fighter pilots:

1️⃣ Observe – Gather information about the situation.
2️⃣ Orient – Analyze your observations in the context of your goals, competition, and biases.
3️⃣ Decide – Make the best call based on your understanding.
4️⃣ Act – Execute, gather feedback, and adjust.

Then, repeat the loop. The faster you cycle through it, the greater your advantage. Leaders who hesitate between Orient and Decide get stuck in data overload. Avoid this trap—make the call, act, and adjust as needed.

Momentum Beats Perfection

Waiting for the perfect decision is a mistake. Instead of chasing certainty, ask: What’s the next small step we can take in the right direction? Then take it. Observe the results. Adjust.

A bias for action builds confidence—not just for you, but for your entire team. When you foster quick, informed decision-making and create psychological safety, your team will step up, take ownership, and move faster toward results.

Your Turn: Apply It Today

Think about a decision you’ve been overanalyzing. Instead of waiting for perfect clarity, identify one small step you can take right now—then take it.

And if you’ve used the OODA Loop (or another framework) to speed up decision-making, I’d love to hear about it—hit reply and share your experience!

Cheers,
Jeff