# Questions to ask founders: what each one tells you

> Good questions to ask founders test the things a deck cannot show: why this team, how well they know the customer, what they have learned and how they reason about risk. Ask every founder the same core questions in the same order, add follow-ups drawn from their deck and open claims, and judge the substance of each answer against a written rubric rather than how confidently it was delivered.

Source: https://delsivo.com/questions-to-ask-founders · Updated 2026-11-06

Most first meetings with founders run on habit. A partner asks the questions they always ask, in whatever order the conversation goes, and leaves with an impression. Impressions are not useless, but they are hard to compare across forty founders in a month, and they drift towards whoever pitched most smoothly.

These are the questions to ask founders in a first conversation and, more importantly, why each one is worth the time: what it tests and what a strong answer contains. It pairs with our list of [founder interview questions](https://delsivo.com/templates/founder-interview-questions), which you can copy. Here the focus is on the reasoning, on asking consistently, and on the research showing that the type of question you ask can shape the outcome.

## Why the questions you ask matter

Investors put a great deal of weight on the team. In a survey of 885 venture investors at 681 firms, Gompers, Gornall, Kaplan and Strebulaev found that the management team was named as an important factor by 95% of firms and as the most important factor by 47%. The qualities investors looked for most were ability, industry experience, passion, entrepreneurial experience and teamwork. A first meeting is where most of that judgement is formed, so the questions carry real weight.

The questions also shape the answers. Kanze, Huang, Conley and Higgins analysed question-and-answer sessions at TechCrunch Disrupt New York City from 2010 to 2016 and found that investors tended to ask men promotion-focused questions (about gains and growth) and women prevention-focused questions (about risks and losses). Entrepreneurs tended to answer in the same focus, and those asked promotion-focused questions raised significantly more funding. The type of question, not only the answer, was linked to the gap in outcomes.

The lesson for any fund is practical: decide your core questions in advance, ask them of every founder, and balance questions about upside with questions about risk for everyone.

## Questions to ask founders, and why each one matters

These cover the areas most first meetings need. Keep the wording open, so founders explain rather than confirm, and leave room to follow up.

Core first-meeting questions, what each tests and what a strong answer includes

| Area | Question | Why it matters | A strong answer includes |
| --- | --- | --- | --- |
| Problem | Who has this problem, and how do they deal with it today? | Tests whether the founder knows a real customer, not a category | A specific buyer, the current workaround and what it costs them |
| Insight | What do you understand about this market that others miss? | Shows original thinking and why now | A concrete observation, ideally learned from customers or past work |
| Team | Why are you the people to build this? | Connects experience to the problem | Specific experience, access or skills, and what the team still lacks |
| Customers | Tell me about your last three customer conversations. | Reveals how close the founder is to users | Names of segments, what was said, and what changed as a result |
| Traction | How do you define your main metric, and how has it moved? | Checks that numbers have definitions and periods | A clear definition, a monthly series and an honest account of dips |
| Go to market | How did your best customer find you, and can that repeat? | Tests whether growth has a repeatable source | A channel with evidence, plus what has not worked |
| Competition | Who else is solving this, and why will customers pick you? | Shows awareness of alternatives, including doing nothing | Named alternatives and a reason grounded in customer behaviour |
| Learning | What is something you believed six months ago that turned out wrong? | Tests how the team updates on evidence | A real mistake, what showed it and what changed |
| Risk | What would most likely stop this working, and what are you doing about it? | Shows judgement about the main risk | A specific risk and a plan or test, not a dismissal |
| Round | What will this round get you to, and by when? | Links the raise to milestones | Milestones, the evidence they would create and a rough runway |

Notice that the last two rows ask about upside and risk. Ask both of every founder. If you only ask some founders what could go wrong, you are running the pattern the Kanze study found.

## Ask every founder the same core questions

Hiring research offers a well-tested model. Google's re:Work guide defines structured interviewing as using uniform methods to assess candidates for the same role: vetted questions relevant to the role, detailed notes of answers, scoring with standardised rubrics, and interviewer training and calibration. Google reports that structured interviews result in increased predictive validity and decreased differences between demographic groups. A founder meeting is not a job interview, but the method transfers.

1. Pick six to eight core questions for your stage and thesis, and ask them in the same order.
2. Write what a strong, an adequate and a weak answer looks like for each one, before you meet anyone.
3. Take notes on what was said, not on how it was said.
4. Rate each answer against the rubric straight after the meeting, before discussing it with colleagues.
5. Compare ratings across the team every few weeks and talk through the ones that differ most.

Judge substance and evidence. Accent, fluency, presentation polish, appearance and background are not evidence about the business, so leave them out of the rating. A founder who answers slowly but precisely has told you more than one who answers smoothly and vaguely. Our guide on [bias in startup screening](https://delsivo.com/reducing-bias-in-startup-screening) covers the wider process.

## Follow-up questions from the deck and open claims

Core questions make founders comparable. Follow-ups make the meeting useful for this company. The best follow-ups come from reading the deck closely and listing what is unclear, missing or worth testing.

- A metric without a definition: the deck says 3,000 active users; what counts as active, and over what window?
- A claim that needs context: 20 enterprise customers; how many are paying, and how many are pilots?
- A gap in the thesis fit: the deck does not mention where the company is incorporated; if that is a hard rule for your fund, ask.
- A jump in the numbers: revenue doubled in March; what happened that month?
- A team gap: no one on the team has sold to this buyer before; how will they learn?

Write follow-ups as questions, not accusations. Most gaps are things a short deck left out. If the answer changes a number, keep both versions in your notes and say which one came from where. The guide on [how to verify startup traction](https://delsivo.com/how-to-verify-startup-traction) explains how to check what you hear, and [how to evaluate a pitch deck](https://delsivo.com/how-to-evaluate-a-pitch-deck) covers reading the deck before you meet.

## Questions to avoid, and common mistakes

Some questions tell you nothing about the business and risk telling the founder a great deal about your fund. Leave out anything about family plans, marital status, age, religion, health or where someone's accent is from. They are not evidence, and in many places they are close to questions employers are barred from asking.

- Leading questions such as 'you have a lot of churn, right?' invite defence, not information. Ask 'how has retention moved?' instead.
- Asking some founders only about risk and others only about growth. Use the same balance for everyone.
- Asking for detailed financial models at pre-seed, when a few clear assumptions would tell you more.
- Spending the whole meeting on the product demo and none on customers or the team.
- Deciding in the first five minutes and using the rest of the meeting to confirm it.
- Promising feedback and not sending it. If you pass, say so clearly and kindly.

## Where Delsivo fits

Delsivo is an AI investment workspace for venture funds, at the design partner stage; nothing is generally available yet. Its interview design follows the approach above: fixed questions from your fund, plus follow-ups drawn from the evidence.

In the first release, Delsivo plans live AI [founder interviews](https://delsivo.com/founder-interviews): the founder shares their screen with the camera on and pitches for about 5 minutes, then an AI interviewer asks your fixed questions out loud, with evidence-driven follow-ups from the pitch, the deck and open claims, within a cap you set of 15 to 20 minutes. A text interview is always available under the same rubric. The AI assesses only the transcript, on substance and evidence, with timestamped citations. Accent, fluency, presentation polish, appearance, background and the video and screen images are excluded from assessment, and analysts decide who advances and can override any assessment with a reason.

In the Pilot, the deck analysis and [claim tracker](https://delsivo.com/features/claim-tracker) are designed to surface the open claims and unknowns your follow-up questions come from, each with a citation to the slide.

## Questions

### What questions do VCs ask founders in a first meeting?

Usually about the problem and customer, why this team, traction and how it is defined, how customers are found, competition, the main risk and what the round will achieve. The useful part is a follow-up on whatever the deck left unclear.

### How many questions should a first founder meeting cover?

Six to eight core questions is enough for a 30 to 45 minute meeting, with time left for follow-ups and for the founder's own questions. Asking the same core set every time makes founders comparable.

### What questions should investors not ask founders?

Anything that is not evidence about the business: family plans, marital status, age, religion, health or background. Also avoid asking only some founders about risk, since research links the type of question to funding outcomes.

### How do you compare founders' answers fairly?

Write what strong, adequate and weak answers look like before the meetings, rate each answer straight after against that rubric, and judge substance rather than delivery. Compare ratings across colleagues regularly.

## Sources

- [Gompers, Gornall, Kaplan and Strebulaev: How Do Venture Capitalists Make Decisions? (NBER Working Paper 22587, September 2016)](https://www.nber.org/papers/w22587) (checked 2026-11-06)
- [Kanze, Huang, Conley and Higgins: We Ask Men to Win and Women Not to Lose (Academy of Management Journal, 2018), London Business School research record](https://lbsresearch.london.edu/id/eprint/1196) (checked 2026-11-06)
- [Google re:Work: A guide to structured interviewing for better hiring practices (updated March 2026)](https://rework.withgoogle.com/intl/en/guides/a-guide-to-structured-interviewing-for-better-hiring-practices) (checked 2026-11-06)

## Related pages

- [Founder interview questions template](https://delsivo.com/templates/founder-interview-questions)
- [Asynchronous founder interviews](https://delsivo.com/asynchronous-founder-interviews)
- [Founder interviews](https://delsivo.com/founder-interviews)
- [Founder interview scoring rubric](https://delsivo.com/features/interview-assessment)
- [Reference check questions](https://delsivo.com/templates/reference-check-questions)
- [How to verify startup traction](https://delsivo.com/how-to-verify-startup-traction)