1) Sceptic check
Explain your decision in 60 seconds — to a friend, in writing, or just to yourself out loud. If you hedge or waffle, note exactly where and why.
Test Your Reasoning
You're about to make a call that will shape the next months or years of your work. That deserves more than a gut feeling or surface-level confidence — but it also doesn't require perfection or bulletproof certainty.
This is where you pressure-test your decision before you commit to it. You've assessed your clarity and confidence, but now you need to examine whether your reasoning can withstand normal doubt, external pressure, and the reality of moving forward. Your brain might resist this process — perfectionist thinking tells you reasoning should be flawless, while anxiety whispers that any holes mean the whole decision is wrong. Neither is true.
Many founders make decisions they can't defend to themselves later, not because they're poor decision-makers, but because they skip this reality check. You're grounding your choice in solid logic, not just momentum or wishful thinking.
2) Flip it
Argue the opposite for one minute. If it's surprisingly easy, your reasoning needs shoring up. If it feels uncomfortable, that's normal — keep going.
3) Pre-mortem
It's 6 months later and it failed. List the top 3 reasons — be brutally honest. Design a counter-move for each.
Strong decisions aren't made in isolation. They're tested against different perspectives, alternative viewpoints, and honest self-examination. Go at your own pace — some founders blast through this in 20 minutes, others need a few days to properly chew on it. Both approaches work.
If your reasoning holds up under this scrutiny, you'll move forward with genuine confidence. If it doesn't, you'll catch potential problems now rather than discovering them later when you're already committed. Either outcome is valuable.
In Explore More: the founder who couldn't explain his own decision, red flags that suggest your reasoning needs more work, and why the ability to defend your choice clearly isn't just communication — it's validation.
What This Step Is (And Isn't)
Here's what most founders miss about decision-making: it's not about finding the perfect choice — it's about making sure you can live with the one you're making.
It's not about finding the perfect choice — it's about making sure you can live with the one you're making.
Tom Allen's first approach with Metable:
He'd identified what seemed like an obvious market need in music metadata management and followed all the conventional startup wisdom: found a co-founder, crafted pitch decks, entered competitions. He felt confident in his technical solution and market analysis.
The reality check:
When pressed to explain his reasoning to potential clients and investors, something kept feeling off. "I can see that I can solve their problem," he'd say, but the more he articulated his logic, the more he realised it was built on assumptions rather than validated understanding.
After years of grinding to maybe 15-20 clients, he made the difficult decision to close Metable. The telling moment came eight years later when he got a sales call asking about implementing exactly what Metable had offered. "Where were you when I needed you?" he thought.
This isn't about eliminating risk — every worthwhile decision carries uncertainty. It's about distinguishing between calculated risk and wishful thinking. When you can clearly explain your reasoning to a sceptical audience, you're not just communicating better — you're validating that your logic can withstand real-world pressure.
The goal is simple: if your reasoning crumbles under basic scrutiny, better to discover that now than six months into execution when you're wondering why you ever thought this was a good idea.
Case Study: The Psychology of Overconfident Reasoning
Let's dig deeper into why smart people make decisions they can't later defend — and why this matters for building a sustainable business that can survive market pressures and founder psychology.
93% of American drivers claim to be better than average, which is statistically impossible.
Research by behavioural economists reveals that CEOs classified as overconfident are 65% more likely to make acquisitions, and this overconfidence is surprisingly beneficial for firm performance on average — but only when it's grounded in solid reasoning that can withstand market feedback and operational reality.
The problem isn't confidence itself; it's what psychologists call "overconfidence bias" — our tendency to overestimate our knowledge and abilities. 93% of American drivers claim to be better than average, which is statistically impossible. In business, this shows up as founders who skip the reasoning test because they "just know" their decision is right, then struggle when that confidence meets actual customer behaviour and market forces.
Joe King's mistake:
He'd met his co-founder exactly once in a pub but felt confident they'd work well together. When the relationship inevitably deteriorated and they found themselves deeply in debt with a tool rather than a viable product, King realised he'd made bold assumptions about partnership compatibility without any evidence to support them.
The neural science:
Overconfidence appears to be a relatively stable cognitive disposition that only slowly changes in response to external influences or disconfirming feedback. Your brain actively resists information that challenges your existing beliefs, especially when you've invested time and identity in a decision.
This is why the reasoning test matters for commercial success. It forces you to articulate the logical foundation beneath your confidence, creating a bridge between founder psychology and business reality. When Tom Allen moved to his second venture, Curve, he approached decision-making differently. Instead of grand plans, he asked modest questions: "Can I make £50,000 a year to keep myself going?" When a client said they didn't believe he could deliver quality service for £1,000 a month, he listened. That feedback helped him price appropriately and build a sustainable business that eventually got acquired.
The lesson isn't to become less confident — it's to ensure your confidence is earned through reasoning you can defend to yourself and others, creating decisions that survive both founder doubt and market pressure.
When Your Reasoning Shows Cracks
Want to spot weak reasoning before it costs you months of wasted effort? Here's what tends to reveal itself when founders pressure-test their logic — and what to do about it.
Common reasoning traps:
- The escape artist: Your reasoning centres around getting away from something rather than moving toward something specific. "I need out of my current situation" isn't the same as "I'm excited to build this particular thing."
- The borrowed brain: You're repeating advice from podcasts, books, or successful founders rather than thinking through your specific situation.
- The perfect scenario planner: Your reasoning only works if everything goes according to plan. No competitor response, no market shifts, no internal challenges.
- The deadline drama: "I must decide now" creates artificial urgency that short-circuits proper reasoning.
- The sunk cost trap: "I've already invested so much" becomes the primary justification for continuing, rather than "this is the right next step."
Robin from Zipcar fell into this pattern — she made a hasty 50/50 equity split with co-founder Antje partly to avoid the awkwardness of negotiation, not because she'd reasoned through fair ownership distribution.
This shows up when you struggle to explain why their solution applies to your context. Research shows that experiencing power can lead to overconfident decision-making, but copying someone else's power moves isn't the same as having power yourself.
Tom Allen learned this with Metable — his reasoning assumed labels would immediately see the value of streamlined metadata management, but he hadn't planned for the reality that enterprise sales cycles are slow and complex.
Unless there's a genuine external deadline (funding expires, job offer has a response date), this urgency often masks anxiety about uncertainty rather than real time pressure.
Research on founder behaviour shows this is one of the most dangerous reasoning patterns because it's emotionally compelling but logically hollow.
Here's the thing about reasoning cracks: they're not verdict failures. They're information. When you spot them, you can either shore up your logic with better evidence or acknowledge that your decision is more intuitive than analytical — both are valid approaches, but only if you're honest about which one you're taking.
AI Buddy Prompts
Sometimes it helps to have a thinking partner when you're testing your own reasoning — especially when your brain keeps circling back to the same comfortable conclusions. The AI Buddy can play devil's advocate without the social pressure of explaining yourself to another person.
Try these prompts when you're working through the reasoning test, particularly if you're finding it hard to genuinely challenge your own thinking:
For testing your logic:
- "I'm testing my reasoning before finalising my decision. Here's my current logic: [share your three-step responses]. Can you spot holes in my reasoning or assumptions I might be making? Push back on anything that sounds weak."
- "I've worked through the reasoning test but I'm still not sure if my decision is solid. Based on what I've shared, what does my own logic actually point toward? Am I overthinking this or underthinking it?"
- "Play sceptic for a moment. I need someone to argue against my decision using my own reasoning. Here's what I'm planning and why: [describe decision and reasoning]. What would a sceptical investor or advisor say?"
- "I keep coming back to the same conclusion no matter how I test it. Is that confidence or confirmation bias? Help me figure out if I'm missing something obvious: [share your reasoning process]."
Remember, the AI isn't trying to change your mind — it's helping you understand whether your mind is made up for good reasons. If your reasoning holds up under AI scrutiny, you can feel more confident about it. If it doesn't, better to discover that in a private conversation than in a real-world failure.
The goal isn't perfect reasoning — it's reasoning you can live with when things get difficult.
The Validation Test: Why Clear Reasoning Matters
Here's the deeper truth about reasoning your way through decisions: the ability to articulate your logic clearly isn't just communication — it's validation that you've actually thought it through.
You think you understand something until you try to explain it to someone else. The same applies to business decisions.
Consider Noam Wasserman's research on nearly 10,000 founders: people problems are the leading cause of failure in startups, and most of these problems stem from decisions that seemed reasonable at the time but couldn't withstand the pressure of reality. The founders who succeeded weren't necessarily smarter — they were better at testing their reasoning before committing to it.
This connects to something psychologists call the "illusion of explanatory depth." You think you understand something until you try to explain it to someone else. The same applies to business decisions: you think your reasoning is solid until you try to defend it under sceptical questioning.
Metable approach:
He could explain the technical solution but struggled to articulate why labels would change their workflow for his system.
Curve approach:
The logic was clearer: "Every music business must report royalties, existing solutions don't scale, we can solve that specific problem." When a client questioned whether he could deliver quality service for £1,000 per month, he had the self-awareness to recognise they were right — and adjusted his pricing accordingly.
The validation test works both ways. Strong reasoning gives you permission to move forward with confidence, even when others doubt you. Weak reasoning gives you permission to pause, gather more information, or acknowledge that you're making an intuitive leap rather than a logical conclusion.
Reflection: What would need to change — in your understanding or your circumstances — to make you feel completely confident in this decision? Is that change realistic, or are you waiting for certainty that will never come? Sometimes the strongest reasoning is acknowledging that you have enough information to take the next step, even if you don't have guarantees about the outcome.