Three Questions Every Founder Should Ask

Most expensive technical mistakes share the same root cause: the question that didn’t get asked.

After twenty years of watching projects go sideways, I’ve landed on three questions that catch most of them before they get expensive.

First: “What happens if we’re wrong?” Some decisions are easy to reverse. Others lock you in for years. A wrong database choice might cost you a migration. A wrong vendor choice might cost you your roadmap. Know which kind of decision you’re making before you make it.

Second: “What’s the simplest version that could work?” Not the most elegant. Not the most scalable. The simplest. If you can’t ship a basic version in a week or two, you’re probably solving a bigger problem than you have. Complexity is easy to add. It’s almost impossible to remove.

Third: “What are we optimizing for?” Speed to market? Cost? Flexibility? Reliability? You can’t have all of them, and pretending you can is how projects end up optimizing for nothing. Pick one or two. Let the others bend.

These aren’t trick questions. They’re not even technical questions. But they force the conversation that prevents the six-month rewrite, the vendor lock-in, the architecture that solved the wrong problem beautifully.

Ask them early. Ask them often. Ask them before anyone writes code.

What question do you wish you’d asked sooner?