9 Questions Every Founder Eventually Asks

Founders rarely book a call with a tidy question. They book it because something is stuck, and the something usually shows up disguised as one urgent problem. "Should I raise?" "Why isn't this converting?" "Do I need to hire a designer?"

Almost every time, the real question is a step earlier in a sequence. And the sequence is remarkably consistent. Intercom's founders wrote a book about it, Intercom on Starting Up, laying out the questions a company faces from zero to growth. I keep coming back to their framing because it matches what I see in the room: founders hit these nine questions in roughly this order, whether or not anyone told them the order exists.

Here they are, with the lens I bring to each.

1. What will you build?

Build something you actually understand. The strongest starting signal I look for in a founder is not market size or a clever wedge. It's whether they've lived the problem. Passion for a problem you've felt firsthand is contagious in a specific way: it attracts the first customers who've felt it too, and it carries you through the months where nothing works yet. When a founder lights up describing the problem rather than the solution, I relax. That's the durable fuel.

2. How will you build it?

The smallest thing that solves the real problem, shipped fast enough to learn from. Not the smallest thing you can build, the smallest thing that actually solves it. Those aren't the same, and the gap between them is where a lot of first products die. The goal isn't a minimum viable checkbox. It's the shortest path to putting something in front of a real user so their reaction can shape what comes next.

3. What will you charge?

Pricing is a product decision, and it's iterated, not guessed once and locked. Founders treat price like a number they have to get right on day one, then avoid touching it because changing it feels like admitting a mistake. It isn't. Price is a lever you test the way you test a feature. What you charge signals who the product is for, what it's worth, and what kind of customer you're inviting. Start with a hypothesis, watch how people respond, and adjust.

4. Who should you hire?

Hire for the stage you're in, not the company you imagine. This is one of the most common places I see founders overreach: recruiting for the fifty-person org they hope to become instead of the five-person reality they're in. The senior specialist who's brilliant at scale can be exactly wrong for the ambiguity of pre-product-market-fit. Hire the person who thrives in the mess you're actually in right now.

5. Do culture and values matter?

They do, and not for the reason founders expect. Culture and values are the operating system for every decision you won't be in the room for. Early on you make most calls yourself. That doesn't last. The values you set now are how your team makes good decisions when you're not there, which is soon and often. Vague values do nothing. Specific ones, the kind that would actually let someone say no to a tempting bad deal, do the quiet work of scaling your judgment.

6. How will you find your first customers?

Start with the people closest to the problem, and earn them one at a time. First customers don't come from a growth playbook. They come from you, personally, talking to the people who feel the pain most sharply. It's unglamorous and it doesn't scale, and that's the point. The relationships you build earning those first few teach you more about the product than any dashboard will, and they become the reference stories that win the next batch.

7. How should you think about competitors?

Understand them. Don't obsess over them. Founders swing between ignoring competitors entirely and doom-scrolling their every release. Neither helps. Know what alternatives your customers actually consider, because that's real context. But the company that kills you is almost never the competitor you were watching. It's your own failure to serve the customer in front of you. Keep the focus there.

8. What will you measure?

Pick metrics your team can actually move, aligned to the mission. A metric nobody can influence is decoration. And here's a subtler trap I coach founders through: not every product should optimize for retention. For some products, a user leaving is the mission working. If someone finds the job, the partner, the recovery, or the answer they came for and then leaves, that's good churn, the product succeeded. Bad churn is when they leave because you failed them: too expensive, felt unsafe, wasted their time. Sort those two apart before you set a retention target, or you'll spend quarters optimizing against your own purpose. The distinction comes from The Product Economy, and it's saved more than one founder from chasing the wrong number.

9. How will you grow?

Growth follows a product customers genuinely want. In order: vision first, then customers, then build. Founders reach for growth tactics when the honest problem is that the product isn't yet something people pull toward. You can't out-market that. When founders ask me about growth too early, I usually walk them back to questions one and six, because sustainable growth is what happens after the earlier questions have real answers, not a substitute for them.

The order is the point

Notice these are a sequence, not a checklist. You don't answer them once and file them. You hit them in roughly this order, and you revisit the early ones every time you're tempted to skip ahead. The founder stuck on growth is usually missing an answer back at "what will you build" or "how will you find your first customers." The one paralyzed by competitors has usually stopped talking to their own customers.

And the through-line under all nine: no one knows your customers, product, team, and market like you do. Advice, including this, shows you what worked for other people and hands you tools to adapt. It doesn't prescribe. The founders who do best hold frameworks loosely and hold their customer relationships tightly.

This sequence is exactly what I work through with founders, quickly in a founder discovery sprint when someone needs to pressure-test where they are, or over time in founder product coaching as the questions keep arriving. If you want the structure without the call, the founder discovery roadmap playbook lays out how I sequence the early ones into a now, next, and later.

Wherever you are in the nine, the move is the same: figure out which question you're actually on, and answer that one honestly before you jump to the next.

Sources

• The nine founder questions come from Intercom on Starting Up (Intercom, 2017), which lays out the decisions a company faces from zero to growth. All rights reserved to Intercom; referenced and paraphrased here in my own voice, not reproduced.
• The good churn versus bad churn distinction under question eight comes from The Product Economy (Product School, 2020). All rights reserved; referenced and paraphrased, not reproduced.