First pitch meetings sound improvised but follow a remarkably consistent script. The questions vary in phrasing; the underlying judgments do not. What investors are really doing on a first call is testing a small number of priors, in roughly the same order, against your specific situation. The questions are the surface; the priors are the substance.
What follows is the substance, in the order it usually appears.
I.So, walk me through what you do.
The opener. Sounds informal. Is not.
What is actually being testedWhether you can describe the company in two sentences without jargon. If you take more than ninety seconds, you have already failed the first test. If you reach for buzzwords, you have failed the second.
II.Why now?
The most underrated question in pitch meetings. Founders prepare for "why you" but neglect "why now."
What is actually being testedWhether you understand the structural reason this company is possible in MMXXVI and was not possible five years ago. Technology shifts, behaviour shifts, regulatory shifts, market shifts — name two specifically. Generic answers ("AI is changing everything") do not count.
III.Who are your competitors?
Sometimes phrased as "what's the landscape look like?"
What is actually being testedWhether you have done the work. The wrong answer is "we have no competition." The right answer names two or three plausible alternatives — including "doing nothing" — and articulates your durable edge in one sentence.
IV.What's been your biggest surprise so far?
Disguised as small talk. Not small talk.
What is actually being testedWhether you are intellectually honest about what you have learned, and whether your learning has been substantive enough to update your priors. A founder who has been live for twelve months and reports no surprises has either not been paying attention or is unwilling to admit being wrong in the room.
V.What's your unfair advantage?
Often phrased as "why you?" or "what makes you the right people to build this?"
What is actually being testedWhether the answer is structural (network effects, data moat, regulatory edge, deep customer relationship) or merely personal (hard work, passion, vision). Personal advantages are necessary but not sufficient. Investors want to back companies whose moat compounds even when the founders are tired.
VI.How are you acquiring customers?
The traction question, asked from the GTM side.
What is actually being testedWhether the channels you describe are repeatable. "We've grown through word of mouth" is fine at pre-seed; at Series A it signals you have not yet found a paid channel that works. Have a clear answer about CAC, payback period, and which channels you've ruled out and why.
VII.What does the next eighteen months look like?
The use-of-funds question, asked obliquely.
What is actually being testedWhether you have specific milestones, mapped to specific hires, mapped to specific outputs. Vague answers ("we'll scale the team and grow the product") suggest you haven't thought hard enough about the next round.
VIII.What keeps you up at night?
An invitation to be honest. Most founders decline it.
What is actually being testedWhether you are aware of your real risks. A founder who lists no concerns sounds either oblivious or rehearsed. A founder who names one or two specific, plausible risks — and what they would do about them — sounds like someone who has done the work.
IX.Why this market and not the adjacent one?
The wedge question. Often comes from partners who have looked at the space.
What is actually being testedWhether you have a deliberate beachhead and a credible plan to expand from it. The wrong answer treats the wedge as accidental. The right answer treats it as the chosen first beachhead in a larger sequence you can describe.
X.How are you thinking about defensibility long-term?
Almost always asked at the Series A stage and later. Sometimes asked at seed.
What is actually being testedWhether your moat is durable. Switching costs, network effects, regulatory advantages, data assets, brand strength — name the specific mechanism that compounds for you over five years.
XI.What's the team gap?
A trust question. Investors are testing whether you know what you don't know.
What is actually being testedWhether you can name the role you most need to hire, and why. Founders who claim no gaps trigger immediate scepticism. Founders who name the gap and the timeline for filling it sound competent.
XII.What questions should I be asking that I'm not?
The closer. The single most useful question in pitch meetings, asked by the best partners.
What is actually being testedWhether you are confident enough to lead the conversation, and self-aware enough to know what is most material about your company that hasn't surfaced yet. The wrong answer is "you've covered it all." The right answer is the specific thing you wish they had asked about — and your answer to it.
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