Questions investors ask founders are useful only when they survive contact with the evidence. This guide builds the framework that does.
Every investor has a checklist they run through in the first ten minutes of a first call. The questions vary in surface form, but they are always probing the same five things. Knowing what those five things are, and why they matter, changes how you prepare.
Who is the buyer, and have you sold to one?
This is not a sales question. It is a reality-check question. The investor wants to know whether you have identified a specific human being with a budget and a problem, or whether you are still working with a persona. "Mid-market fintech compliance officers" is a persona. "The VP of Compliance at a 200-person payments company in Austin who is currently using a spreadsheet and two contractors to manage SOC 2 evidence collection" is a buyer. The investor can tell the difference in about 30 seconds.
What does it cost to get one customer?
Again, not a financial question in the first instance. They want to know whether you have mapped the sales motion. Who signs the contract? Who influences the decision? What is the procurement process? How long does it take from first contact to payment? If you cannot answer these, you have a product that may or may not be a business.
Who else is solving this problem?
The answer "no one" is almost never correct and immediately signals that the founder has not researched the space carefully. Every problem has a current solution: a spreadsheet, a consultant, a workaround, a legacy tool. The investor wants to hear you describe that landscape accurately, which means you have to know it.
Why will the customer switch?
The switching question is about inertia, not features. Buyers have switching costs: training time, integration work, political capital spent on approvals, the risk of a failed rollout. Your answer to this question needs to explain why those costs are worth bearing. "Our product is better" is not an answer. "The current tool fails in a way that costs $4,200 per year and requires three manual corrections per month, and our tool eliminates that failure entirely" is an answer.
What do you need to be true for this to work?
This is the kill criterion question in disguise. The investor is asking you to name your assumptions. If you have done this work, you have a list. If you have not, you will find yourself naming a risk factor instead of an assumption, and the investor will notice the difference.
The reason these five questions show up in every first meeting is not that investors lack imagination. It is that the answers reveal whether the founder is operating from evidence or from conviction. Conviction without evidence is a starting point. Evidence without conviction is analysis. The combination is the thing worth funding.
Preparing for these five questions before you build the deck is more useful than optimizing the deck itself.
The actual five questions, and what each tests
The first question is some variant of "Why now?" The investor is testing whether you can name a non-trivial change in the world that opens this opportunity today and not three years ago. Generic answers about "AI getting better" do not survive the follow-up. Specific answers about a regulatory change, a platform shift, a buyer behavior change with measurable evidence, or a cost-curve crossover are what work. Andy Rachleff at Wealthfront has written about why the timing thesis is harder than the product thesis, and the writing is widely cited because it lays out the mechanism clearly.
The second question is "Who is the customer?" The investor is testing whether you have an ICP definition tight enough to write a cold email to. "SMBs" is not an ICP. "Practice managers at outpatient mental health groups with two to ten clinicians who use SimplePractice and bill insurance" is an ICP. The narrowness of the ICP is the signal. If you cannot describe the customer in a sentence that includes a job title, a tool they use today, and a count, the investor knows the rest of the model is built on sand.
The third question is "What changes for the customer when they buy this?" Not features. The change. "A two-hour weekly process becomes a 15-minute process" is a change. "Better workflow" is not. The Lean Startup tradition calls this the value hypothesis, and a clean answer typically references a quantified before-and-after rather than a qualitative description.
The fourth question is "How will you reach them?" This is the GTM proxy. If the answer is "content marketing" or "Google Ads" at pre-seed, the investor knows the founder has not done the math. If the answer is "the first ten will come through three specific Slack communities where I am already active, the next thirty through warm intros from those ten, and the cohort after that will tell us which paid channel converts on the LTV math," the investor knows you have a plan that will survive contact with reality.
The fifth question is "What would change your mind?" The kill criterion question. Most founders answer this badly because they have not actually written one down. The right answer names a specific, measurable threshold and the test that would reach it. "If our cold conversion rate stays below 4 percent after two months on a tightly targeted list, the wedge is wrong" is the right shape. "We’ll iterate based on feedback" is not.
What the answers reveal
Each answer is a proxy for whether the founder has done the work. The "Why now" answer reveals reading. The "Who" answer reveals customer conversations. The "What changes" answer reveals product clarity. The "How will you reach them" answer reveals CAC math. The "What would change your mind" answer reveals epistemic honesty. A founder who nails three of the five is fundable on potential. A founder who nails four is a top-of-funnel priority. A founder who nails all five usually has term sheets already.
The corollary is also useful: if you cannot answer one of the five cleanly, do not spend another hour on the deck until you can. The deck is a delivery mechanism, not the work. The investor is measuring the work, not the deck. Y Combinator’s application guide is structured around exactly these five tests for the same reason: they correlate with founders who execute, not founders who pitch.
The last thing worth saying is that these questions show up in different forms across different stages. Pre-seed investors weight the "Who" and "Why now" answers heaviest because the product is still hypothetical. Series A investors weight the "How will you reach them" answer heaviest because the GTM motion is now the constraint. The questions stay the same; the weights shift. Building the answers as a single living document, not a deck, is how the same work compounds across multiple rounds.