Thinking, Fast and Slow
Thinking, Fast and Slow
Learning should be useful. Insight is only helpful if you can apply it. These questions are here to help you do both. This read-along companion breaks down each section of the book with the goal to help you connect the ideas to real decisions you're making in your business, your leadership, or your day-to-day life.
PART 1: TWO SYSTEMS
Concepts: System 1 (fast, automatic) vs. System 2 (slow, deliberate)
Where in your work are you relying on instinct because it feels familiar, not because it's actually working?
Why we're asking: System 1 is fast and effortless, but it's also biased. This helps reveal where habits might be guiding decisions more than data or strategy.
What decisions feel urgent on the surface, but probably deserve more time than you’re giving them?
Why we're asking: System 2 requires effort, so we avoid it. This question helps you spot when urgency is a reflex instead of a real priority.
When have you mistaken confidence for competence, either in yourself or someone else?
Why we're asking: System 1 can be overly confident, even when wrong. This highlights overconfidence bias in fast judgments.
Where do you reward speed in your team but overlook thoughtfulness?
Why we're asking: Teams often value quick decisions, but that can discourage deeper thinking. This helps identify where the culture may prioritize reaction over reasoning.
Which tasks do you keep avoiding because they feel mentally expensive to start?
Why we're asking: Effortful thinking is metabolically costly. Avoidance often means your brain is trying to conserve energy, not that the task doesn’t matter.
PART 2: HEURISTICS AND BIASES
Concepts: Anchoring, availability, representativeness, base rate neglect, framing
What starting point is shaping this decision more than it should?
Why we're asking: Anchoring bias causes early information to overly influence outcomes. This question helps you name and neutralize it.
Are recent examples skewing how you're assessing risk or opportunity?
Why we're asking: The availability heuristic favors vivid or recent events, not representative ones. This helps balance gut reactions with real probability.
Where are you trusting your gut because something "seems right," but you haven’t checked the math?
Why we're asking: Representativeness bias leads us to judge similarity over actual statistics. This exposes when a pattern match is misleading.
How would your decision shift if you framed the same information differently?
Why we're asking: Framing effects change how people perceive value and risk. This invites you to test your messaging or mindset from multiple angles.
What data have you ignored because it doesn't match the story you’ve already decided on?
Why we're asking: Base rate neglect happens when we overlook general trends in favor of specific narratives. This helps ground your thinking in what's statistically true.
PART 3: OVERCONFIDENCE
Concepts: Illusion of understanding, hindsight bias, planning fallacy, narrative fallacy
What feels obvious now, but wasn’t clear at the time?
Why we're asking: Hindsight bias makes outcomes feel predictable after the fact. This helps separate luck from insight.
Where are you underestimating how long something will really take?
Why we're asking: The planning fallacy causes us to downplay time, cost, and complexity. This brings realism into your roadmap.
What are you "sure" will work, but haven't pressure-tested outside your own head?
Why we're asking: We tend to overestimate our own judgment, especially with limited data. This invites humility before launch.
What would a smart outsider say you're missing right now?
Why we're asking: The illusion of understanding keeps us inside our own bubble. This pushes for outside-in thinking.
Where are you telling a clean story that skips over the messy parts?
Why we're asking: Narrative fallacy smooths over complexity, which can hide risk. This helps identify where simplification becomes dangerous.
PART 4: CHOICES
Concepts: Prospect theory, loss aversion, endowment effect, reference points
What are you holding onto because it’s yours, not because it’s still valuable?
Why we're asking: The endowment effect makes us overvalue what we already own. This challenges sunk cost thinking.
Are you more afraid to lose than excited to win?
Why we're asking: Loss aversion creates a stronger emotional response to risk than to reward. This helps you check whether fear is driving your strategy.
How is your current "normal" shaping what feels possible right now?
Why we're asking: Reference points anchor expectations. This surfaces how context may be limiting ambition.
What would this decision look like if you zoomed out six months?
Why we're asking: Prospect theory shows that short-term framing can distort value. This encourages long-view thinking.
What tradeoff are you trying not to make but probably need to?
Why we're asking: People avoid hard choices by reframing or delaying. This helps bring clarity to necessary sacrifice.
PART 5: TWO SELVES
Concepts: Experiencing self vs. remembering self, peak-end rule, duration neglect
Are you building a business that feels good while you're living it or only when you're looking back on it?
Why we're asking: We often optimize for memory, not experience. This helps realign decisions toward actual daily fulfillment.
What would change if you valued how something feels just as much as how it looks later?
Why we're asking: This question bridges the two selves. It encourages building a life that’s both livable and meaningful to remember.
What moments from the past month do you actually remember and why those?
Why we're asking: The peak-end rule shapes memory based on emotional intensity, not duration. This reveals what your brain thinks is worth keeping.
What part of your day feels like a time suck, but you couldn’t even say what you did after?
Why we're asking: Duration neglect means we overlook the total experience and focus on specific highlights. This invites a redesign of your time.
How often do you design for the story instead of the substance?
Why we're asking: The remembering self cares about the story you’ll tell later, not how it actually felt at the time. This checks whether you're sacrificing depth for optics.