The Decision Trap🪤 - Why Your Best Decisions Are Your Biggest Mistakes🚫

September 4, 2025

Hi Reader

Part 2 of “The Confidence Series”

I used to be proud of my decision-making track record.

Quick analysis. Clear choice. Confident execution. Results that “proved me right.”

Then I started working with top leaders who made decisions that looked terrible on paper but delivered extraordinary outcomes.

It puzzled me and so I sat with it until I realised something uncomfortable.

My "best" decisions were often preventing me from making truly great ones.

The very approach that built my confidence was actually my glass ceiling.

Let me show you why. I think you’ll find it valuable….

The Success Pattern That Creates Failure

Here's what conventional wisdom teaches you about decision-making….Gather data. Analyse options. Choose the best path. Execute with confidence. Repeat.

And you know what? This approach works beautifully for predictable problems.

But elite leadership operates in unpredictable environments where yesterday's "best practices" become tomorrow's competitive disadvantages.

The Amateur Decision Pattern: Find the objectively best choice and commit fully.

The Expert Decision Pattern: Make the best available choice while staying alert for why it might be wrong.

The difference is philosophical AND practical.

The Confidence Trap in Decision-Making

When you make decisions that work out well, your brain creates a dangerous story: "I'm good at making decisions because I choose correctly." A blend of survivorship bias and confidence bias.

This all feels empowering but, I now know, it's actually quite limiting.

Because it trains you to optimise for being right instead of optimising for learning.

Let me give you an example.

You research thoroughly before deciding. You defend your choices vigorously. You implement with unwavering commitment.

Your successful decisions reinforce this pattern. Your failed decisions get explained away as "unforeseeable circumstances."

Meanwhile, the most successful leaders I work with operate differently. They make decisions designed to be proven wrong quickly if they are wrong. You could draw parallels with the ‘revolving door’ philosophy Amazon have towards deciding on new innovations.

The 48-Hour Test

If you’re still curious then you’ll want to know what is next from a practical perspective. Here's a diagnostic that separates confident decision-makers from effective ones:

After making an important decision, track your mindset for 48 hours.

Pattern A (Confidence-Based):

You look for evidence that confirms your choice
You feel uncomfortable when people raise concerns
You interpret early positive signs as validation
You become defensive about potential problems

Pattern B (Learning-Based):

You actively seek evidence that challenges your choice
You encourage people to identify potential issues
You treat early positive signs as data points, not proof
You become curious about potential problems

Pattern A feels more confident. Pattern B creates better outcomes.

Why Your Smartest Decisions Limit Your Growth

A luxury hospitality CEO attuned me to this lesson accidentally.

She'd built her reputation on making smart, well-researched decisions that consistently worked out. It was quite the source of professional pride.

Her process was impressive: Comprehensive analysis. Stakeholder consultation. Risk assessment. Clear reasoning.

But when market conditions shifted unexpectedly, her thorough approach became a liability.

While she was perfecting her analysis, competitors were road-testing multiple approaches and adapting in real-time.

Her "smart" decision-making process was optimised for being right in stable environments. But what about when stability disappears?

The Two Types of Decision Confidence

Static Confidence: "I've made the right choice and will execute it flawlessly."

Dynamic Confidence: "I've made the best choice available and will adapt as I learn more."

Static confidence feels stronger. It projects certainty and leadership. In truth, it’s from and serves your ego.

Dynamic confidence performs better. It enables rapid course correction when reality differs from prediction.

The difference shows up in how you handle unexpected information after deciding.

Static Confidence Response: "This doesn't change anything. We stick to the plan."

Dynamic Confidence Response: "This is interesting. How does this affect our assumptions?"

The Elite Leader's Decision Framework

Having looked closely at this, as I see it leaders who sustain excellence in unpredictable environments operate from three counterintuitive principles:

Principle 1: Optimise for Learning Speed, Not Accuracy Rate

Instead of trying to make perfect decisions, they make decisions that will teach them quickly whether they're right or wrong. (remember the Amazon ‘revolving door’?)

They choose paths with fast feedback loops over paths with theoretically better outcomes.

Principle 2: Plan for Being Wrong

They plan for success. And they also plan for specific ways their decision might fail and what they'll do when (not if) those failures occur.

This isn't pessimism. It's preparation for adaptation. They know life throws curveballs and not garlands.

Principle 3: Separate Decision Quality from Outcome Quality

They evaluate their decisions based on the process and information available at the time, not on how things eventually worked out.

This prevents both overconfidence from lucky outcomes and under-confidence from unlucky results.

Over to You

Now time to help you hit the ground running.

Try this Decision Confidence Assessment.

Look at your two most recent important decisions.

For each, ask:

Before deciding:

Did I spend more time confirming my preferred choice or challenging it?
Am I optimising to be right and/or win an argument or to learn quickly?
What would I do if early signs suggest I'm wrong?

After deciding:

How do I respond when people raise concerns about my choice?
What evidence am I actively seeking. Do I want confirmatory or contradictory?
How quickly could I (and those around me) recognise and correct course if needed?

The answers point towards whether you're making decisions or making commitments.

The Adaptation Advantage

When you make decisions designed for learning rather than proving rightness, several things happen:

Correction Speed Increases: You spot problems weeks or months earlier than leaders committed to their original choices.

Innovation Expands: You discover opportunities that rigid execution would miss.

Team Confidence Grows: People trust leaders who adapt to new information more than leaders who ignore it.

Stress Decreases: When being wrong becomes data rather than failure, decision-making pressure reduces dramatically.

Your Implementation Challenge

For your next important decision, try this:

Step 1: Make your choice based on current information.

Step 2: On your own and with then with others, identify 2-3 specific ways you might be wrong.

Step 3: Define what early evidence would suggest each potential error.

Step 4: Create checkpoints to actively look for that evidence.

Step 5: Commit to the decision while staying alert for the signals that suggest adjustment.

These steps may feel clunky at first but like any practised skill they become second-nature over time. They aren’t there to highlight indecision disguised as flexibility but to illustrate confidence that includes adaptation capacity.

Beyond Right and Wrong

With this approach, your goal is to make decisions that evolve and improve through implementation rather than make perfect decisions.

Static confidence says: "I've figured it out." Dynamic confidence says: "I'm figuring it out."

The difference determines whether your decision-making gets better or just gets more rigid over time.

Think about it…Your best decisions aren't your most defensible decisions, they're likely your most adaptable ones that are on an upward spiral.

Next week in our confidence series: "The Team Trap: Why Your Leadership Style Is Destroying Team Performance". We’ll unpack how the approaches that make you feel like an effective leader can prevent your team from becoming truly exceptional.

P.S. Do you recognise patterns of static confidence in your decision-making? Or does it feel like a good idea to explore how to maintain conviction while staying alert for course correction opportunities? Both could be the basis for a solid conversation

The most effective leaders understand that confidence in decisions comes not from being certain about outcomes, but from being certain about their ability to adapt when outcomes differ from expectations. Our first conversation is without charge…arrange it now at https://calendly.com/p_clarke/20min