Most founder advice gets this backwards

You're told to move fast, trust your gut, ship before you're ready. Then you're told to be thoughtful, gather data, consider all options. The advice contradicts itself because everyone's optimizing for different failure modes.

What if the problem isn't that you need better advice? What if you just need better questions?

I've watched founders make the same decision-making mistakes for years. Not because they're bad at deciding. Because they're stuck in their own context. They can't see what they're not seeing.

So I started tracking which questions actually helped. Not the ones that sound smart in retrospect. The ones that shifted something in real time. Turned out there were five that kept coming up.

How can I see this with fresh eyes?

You're too close to your own product. You've been thinking about this hiring decision for weeks. You know too much context, and all that context is making you dumber.

Fresh eyes means: What would someone who just walked into this see? What if you learned about this problem yesterday?

I watched a founder spend three months optimizing a feature that users barely touched. When I asked "If you were building this company from scratch today, would this feature exist?" he went quiet. Shipped a completely different thing the next week.

The trap is thinking experience helps. Sometimes it just gives you more reasons to keep doing the wrong thing.

What might I be assuming?

Assumptions hide. They're the things you don't think to question because they feel true.

Saw this play out with a B2B company last year. They assumed their customers needed better reporting. Built an entire dashboard. Turns out customers just wanted a weekly email. The "reporting problem" was actually a "too much work to log in" problem.

Your assumptions aren't even beliefs you hold. They're beliefs you don't know you hold.

Try this: Take whatever you're working on and write down what has to be true for this to work. Then ask: Do I know that's true, or do I just think it's true?

Am I rushing to judgment?

Fast decisions feel like progress. But there's a difference between moving quickly and cutting off options before you've actually looked at them.

The pattern I keep seeing: Founder gets a piece of information. Forms an opinion in the first 30 seconds. Then spends the next two weeks gathering evidence to support that opinion.

You're not analyzing. You're justifying.

The fix isn't slowing down. It's catching yourself before you lock in. When you notice you've already decided, pause. What would change your mind? If the answer is "nothing," you're not thinking anymore.

What am I missing?

Different question than "What don't I know?" You don't know infinite things. That's not useful.

What you're missing is: What's in the room that you're not looking at?

A founder I know was losing customers after month two. Talked to 15 of them, asked why they left. Got vague answers about fit and timing. Then someone on his team said "Did you notice they all signed up the same week we ran that campaign?" Different acquisition source, different expectations, completely different problem.

He wasn't missing data. He was missing the pattern in the data he already had.

Ask: What would someone smarter than me see here that I'm not seeing?

What matters most?

You can't do everything, but you keep acting like you can. You've got eight priorities. Which means you've got zero priorities.

This is the question that makes founders uncomfortable because it forces trade-offs. You want speed and quality and low burn and happy team and perfect product-market fit. Pick two, maybe three.

Every time I see a founder stuck, it's because they won't choose. They're trying to optimize for too many things at once. They end up with a strategy that sounds good on paper and does nothing in practice.

The test: If you had to kill half your roadmap today, which half would you kill? Whatever's left is what actually matters. The rest is noise.

Frameworks give you structure. Questions give you awareness.

Structure's great when you know what problem you're solving. But most founder decisions aren't clean enough for frameworks. You're working with incomplete information, shifting contexts, and constraints that change weekly.

Questions don't tell you what to do. They help you see what you're actually dealing with.

I used to think the best founders were just better at deciding. Now I think they're better at noticing what they're deciding about. They catch their own blind spots faster.