Ask What Would Make This Decision Wrong Before You Ask What Would Make It Right

A competitor suffers a data breach. The story runs on LinkedIn for two weeks. Three executives testify before a parliamentary committee. A month later, your leadership team sits do…

(A note before we start: I wrote about sunk cost briefly in the June 18 issue — specifically how the model breaks down when building costs collapse. That was about when the framewo…

You walk into a salary negotiation having done your homework. You know the market rate. You have a number in mind. Then the hiring manager opens with something lower than you expec…

Here's a pattern that shows up in deal post-mortems with uncomfortable regularity: the red flags were visible in the data room. They were there in the financials, in the customer c…

Somewhere in a boardroom after the 2008 financial crisis, a risk committee added "mortgage-backed securities" to their list of things to worry about. Which would have been useful a…

Meta spent over $80 billion building a virtual world that peaked at 300,000 monthly active users — and then kept spending. Reality Labs lost $19.2 billion in 2025 alone on $955 mil…

A student in a Harvard Business School negotiation simulation spent most of the exercise arguing, with genuine conviction, that a wage rate of $10.69 per hour was completely unreas…

Most strategy sessions start with a question like "How do we make this succeed?" It sounds rigorous. It isn't. It's optimism wearing a whiteboard. The more useful question — the on…

A single data breach story in the news can temporarily tank conversion rates across an entire industry. Not because the actual risk of fraud increased. Because the mental availabil…

You're in a product review meeting. The feature has missed its adoption targets for three quarters running. The engineering team has quietly stopped believing in it. Two of your be…

Here's a strange experiment. Researchers spin a roulette wheel — rigged to land on either 10 or 65 — then ask participants to estimate the percentage of African countries in the Un…

After the 2001 anthrax attacks, Americans flooded emergency rooms with anxiety about bioterrorism. Billions in federal funding shifted toward biodefense. Meanwhile, the flu killed…

Here's a question worth sitting with: if 90% of startups fail, why does almost all startup advice come from the 10% that succeeded? The answer is obvious once you say it out loud.…

You're three months past the original deadline. The budget has been revised twice. The team is tired. And in your last status meeting, you caught yourself explaining — again — why…

You've been working on this for eight months. The team is good. The original idea was sound. You've spent real money — maybe a lot of it. And now the data is telling you something…

Setup: The Interview That Was Already Over Picture a hiring panel debriefing after a final-round interview. The candidate was technically strong — maybe the strongest in the pool.…

There's a version of opportunity cost that lives in economics textbooks. It's clean, rational, and almost insultingly simple: every choice forecloses other choices, so the real cos…

You know what opportunity cost is. You've known since Economics 101. Every choice forecloses other choices; the real price of option A is whatever you gave up by not choosing optio…