Bad Decisions Can Masquerade as Good Ones

Smart people make bad decisions all the time; not because they’re reckless, but because hidden cognitive biases warp their judgment. The problem isn’t intelligence. It’s awareness.

These invisible distortions affect how we interpret information, assess risk, and make choices in leadership, strategy, and daily life. Becoming a better decision-maker starts by learning to recognize and neutralize them.

In today’s newsletter I’ll explore four of the most damaging and common cognitive biases, and give you tools to catch them in the act.

The Power Move: Metacognition

If biases distort how we think, then spotting them means we’re thinking about how we think. Very meta.

Actually, it’s metacognition. It’s a recurring theme here for a reason.

It’s one of the highest-leverage skills you can develop. When you practice metacognition, you don’t just think better, you build better habits and make better decisions that shape the outcomes you care about.

Skip this layer of awareness, and you’re stuck in Groundhog Day; repeating the same patterns, with the same results, while your biases run quietly in the background.

In the rest of today’s issue, you’ll learn how to recognize four major biases in your own thinking, and how to counter them before they sabotage your next decision.

The Anti-Bias Toolkit

While the list of cognitive biases is long, the four we’ll explore today are among the most powerful, especially for leaders and knowledge workers.

What’s fascinating is how each one distorts our judgment in a slightly different way. Even worse, they often stack together, amplifying each other (but we’ll save that exploration until the end of this series, if you’re interested).

1️⃣ Incentive-Caused Bias

What it is: People may distort their decisions when their incentives point in a different direction than the truth.

Examples:

• The Wells Fargo scandal: Employees opened fake accounts to meet aggressive quotas because that’s what the incentives encouraged.
• Doctors: When drug reps wine and dine physicians, prescription rates go up, even if the doctor believes they’re making independent choices. (This is why many organizations ban gifts in their code of conduct.)
• Sales: A salesperson incentivized on volume may ignore customer fit, resulting in high churn.

Why it matters:

• Incentives distort judgment, even when we think we’re being objective.
• This applies to more than money: status, praise, promotions, job security all count.
• Metrics are a form of incentive, because they drive the subsequent rewards.
• Incentives shape behavior more reliably than rules or values. If you want to understand why someone did something, follow the incentives.

How to spot it: Ask yourself:

• “What would I do if my incentives were different?”
• “Who benefits from this choice, and how?”
• “What behavior is this system actually encouraging?”
• “Would I still make this decision if there were no personal upside?”

How to counter it:

• Design: Create incentives that align long-term goals with short-term behavior.
• Make incentives visible: Hidden drivers are harder to debug.
• Add checks and balances when someone’s incentives could distort objectivity.
• Use second-order thinking: What happens when everyone responds to this incentive?

“No matter how clear your leadership principles and yearly plan may be, they speak softly in comparison to financial incentives. Money talks—if your leadership principles, your yearly plan, and your financial incentives are not closely aligned, you won’t get the right results.”

— Colin Bryar and Bill Carr in “Working Backwards”

2️⃣ Confirmation Bias

What it is: The tendency to seek out, interpret, and remember information in a way that confirms our existing beliefs or decisions, while discounting or ignoring evidence that contradicts them.

Examples:

• Hiring: You like a candidate’s vibe, so you subconsciously overweight everything they say that confirms your initial impression.
• Investments: You buy a stock, then read bullish articles and ignore bad news.
• Social Media: These apps show you what aligns with your past engagement, reinforcing your worldview.

Why it matters:

• It creates false confidence: Everything you see supports your belief, but only because you filtered out the rest!
• It leads to bad decisions that feel good.
• It short-circuits learning: You stop exploring once you “know” the answer.

How to spot it: Ask yourself:

• “What evidence would convince me to change my mind?”
• “Am I looking for truth or for validation?”
• “If someone else made this decision, what would I question about it?”

Also look for:

• Being selective on quoting sources.
• Groupthink, or excessive agreement.
• Emotional certainty that isn’t backed by data.

How to counter it:

• Seek disconfirming evidence (e.g. “We won’t proceed unless we’ve explored at least 3 challenges to this idea.”)
• Devil’s advocate: Give someone permission and responsibility to run counter to the prevailing view.
• Fresh eyes: Ask someone not invested in the idea to review it.

“Flaws in forming and updating beliefs have the potential to snowball. Once a belief is lodged, it becomes difficult to dislodge. It takes on a life of its own, leading us to notice and seek out evidence confirming our belief, rarely challenge the validity of confirming evidence, and ignore or work hard to actively discredit information contradicting the belief. “

— Annie Duke in “Thinking in Bets”

3️⃣ Overconfidence Bias

What it is: The tendency to overestimate your own knowledge, skill, or ability to predict outcomes, especially in complex or uncertain environments.

Examples:

• Entrepreneurship: New founders ignore negative signals because they believe in their vision too strongly.
• Forecasting: Giving narrow predictions (“We’ll launch in 60 days”) despite a long track record of delays.
• Investing: Individuals trade stocks thinking they can beat the market, even though most professionals can’t.
• Project Management: Teams don’t build in slack or contingency plans.

Why it matters:

• Confidence is not the same as accuracy, but your brain often can’t tell the difference!
• It leads to skipped validation, underestimating risk, and poor hedging.
• It can suppress dissent and fast-track bad decisions, especially in group settings.
• Ironically, the more skilled or experienced you are, the more vulnerable you may be.

How to spot it: Ask yourself:

• “Am I mistaking confidence for competence?”
• “What’s the probability I’m wrong?”
• “Have I seen similar situations go off track, and why?”

Also look for:

• Extremely tight confidence intervals (“We’re 100% sure”)
• Dismissing risks as “low probability” without analysis
• Resistance to contingency planning

How to counter it:

• Run a premortem: Imagine the decision failed. Why? What went wrong?
• Use base rates: What usually happens in this scenario?
• Use ranges: Replace “30 days” with “We’re 80% confident it’ll take between 30 and 60 days.”
• Slow down: Pause to re-check assumptions before major decisions.

“She is very confident in her decision, but subjective confidence is a poor index of the accuracy of a judgment.”

— Daniel Kahneman in “Thinking, Fast and Slow”

4️⃣ Sunk Cost Fallacy

What it is: The tendency to continue investing in a decision, project, or path based on the resources already spent (time, money, energy) even when it’s no longer the best choice.

Examples:

• Personal relationships: Staying together because “we’ve been together for years,” not because it’s working now.
• Career: Remaining in a job you dislike because you’ve already invested years building in that company.
• Public works: Governments continue infrastructure projects long after costs balloon, because to cancel would “waste” what’s already spent.
• Projects: A company pours resources into something no longer necessary because it’s already 80% done.

Why it matters:

• Escalation of commitment: The more you’ve invested, the harder it is to let go.
• It traps people in status preservation (“I can’t admit I was wrong”), leading to bigger losses.
• Organizations stay anchored to failing initiatives because of sunk time, effort, and political capital.

How to spot it: Ask yourself:

• “What would someone with no history here advise?”
• “If I hadn’t already invested X, would I choose this again today?”

Also watch for:

• Resistance to killing a project, even when new data says you should.
• “We’ve come this far. We have to finish it.”
• “We can’t waste all that effort.”

How to counter it:

• Establish kill criteria: Pre-commit to clear stopping points before launching: “If we haven’t achieved X by Y, we stop.”
• Start fresh: Pretend there’s a new decision-maker evaluating this. What would they do?
• Fresh eyes: Bring in someone uninvolved to make an objective assessment.

“The more time you sink into the wrong idea, the more you are misspending life’s most precious resource. But if you quit at the right time (and ignore that sunk cost), then you can move on to scale something else—something with a better shot at success.”

— John A. List in “The Voltage Effect”

Bringing It All Together

You can’t eliminate bias, but you can get better at catching it in the act!

The more you practice, the sharper your instincts become. Over time, you’ll make clearer decisions, feel fewer regrets, and spend less energy second-guessing yourself. 😁

Like we learned in metacognition, practicing skills like bias-recognition begins to rewire your brain to do this automatically; unconscious competence at its finest!

These ideas have been top of mind for me lately as I make big transitions.

Sunk cost came up when I left Atlassian after 10 years. I had deep context, credibility, and momentum there, but was that a good reason to stay? I asked myself: “If I weren’t already here, would I choose this?”

I’m considering a new opportunity helping a founder build something challenging. I’m confident I can do it, but that triggered me to check on overconfidence: is my belief rooted in competence, or blind optimism? I did some digging, and base rates suggest the odds of success are low (around 15%). Should I pursue it, or spend my time where outcomes are more likely? 🤔

I don’t have perfect answers, but I’m asking better questions. That’s the shift.

You’ll never eliminate bias entirely. But the moment you start noticing it, especially in yourself, you’ve already raised the quality of your decisions.

Call to Action

Thanks for reading this first deep dive into cognitive biases! Next time, we’ll explore the biases that ride on emotion: anger, fear, urgency, and gut instinct.

Until then, pick a real decision you’re facing this week and run it through the lens of these four biases: incentives, confirmation, overconfidence, and sunk costs.

Practicing is a win.

Thinking better starts with noticing more.

Kevin

PS - What’s a decision you’ve made recently where one of these biases might’ve played a role? I’d love to hear about it; just hit reply.