Questions to Ask Investors in First Meeting
Questions for founders in a first meeting with a prospective investor, covering fund mechanics, decision process, what they do beyond writing a cheque, and how they behave when a company struggles. Written for pre-seed through Series A conversations.
The questions
Open any question for the note
What made you take this meeting, and what would you want to see more of?
Why ask it
Their answer tells you which part of the pitch is doing the work. If they cannot articulate a thesis for your business, you are early in their funnel rather than in a live conversation.
What stage and sectors do you usually invest in, and where do we fit?
Why ask it
Funds take exploratory meetings well outside their mandate. If you sit at the edge of it, the process will be slower and the internal champion will need more evidence.
What is your typical cheque size, and do you lead or follow?
Why ask it
This determines whether the meeting can produce a round or only part of one. A follower without a lead in place is not a route to closing, however enthusiastic they sound.
Where are you in the life of the fund, and how much is left to deploy?
Why ask it
A fund in its final year has little reserve capital for follow-ons and may be pressed on exit timing. Founders rarely ask this and it changes the value of the relationship substantially.
Beyond capital, what do you actually do for portfolio companies?
Why ask it
Listen for named functions, such as recruiting help, customer introductions, or a specific operating partner, rather than a claim about being hands-on. Vague answers usually mean a quarterly board call.
Can you give an example of a company you helped in the last year, and what you did?
Why ask it
A concrete story is hard to invent. If the example is about their best-known success, and they were a small cheque in a later round, you are hearing marketing.
What does your decision process look like, and who else has to say yes?
Why ask it
Number of partner meetings, need for consensus, and any investment committee all determine your timeline. Founders lose weeks assuming the person in front of them can decide alone.
How long does it usually take you from first meeting to a term sheet?
Why ask it
You need this to sequence conversations so offers land close together. A fund that takes twelve weeks cannot be run in parallel with one that takes three.
What concerns you about our business, and what would resolve them?
Why ask it
Surfacing objections in the room is better than having them settled without you afterwards. It also tests whether they have thought about the business or only about the market.
What milestones would you expect us to reach with this round?
Why ask it
Their answer is effectively their view of the next raise. If their expectations require growth you know the money cannot fund, you have found a mismatch worth naming now.
What reporting and communication would you expect from us?
Why ask it
Monthly written updates are normal. Weekly calls, ad hoc data requests, or dashboard access are a real operational cost, and it is easier to negotiate before a term sheet than after.
How involved do you want to be in strategic and hiring decisions?
Why ask it
Some founders want that involvement and some do not, but a mismatch here becomes the main source of friction on a board. Ask for examples from existing portfolio companies.
What role would you want: a board seat, an observer seat, or neither?
Why ask it
Board composition outlasts the round. Getting their expectation early lets you design the governance rather than react to a term sheet that assumes it.
How do you approach follow-on funding in later rounds?
Why ask it
Reserve policy determines whether they can support you next time. An investor who never follows on sends a signal to the market when they sit out, whatever the reason.
What happens when one of your companies misses plan or has to pivot?
Why ask it
The most useful question in the set, because it describes your worst quarter. Look for a specific story with a founder still in the seat, not a statement about backing people.
How do you handle disagreements with founders?
Why ask it
Every real relationship has one. An investor who cannot recall a disagreement is either newly deployed or not being candid, and both are worth probing.
Which of your founders could I speak to, including one whose company struggled?
Why ask it
Anyone will offer their happiest reference. The second half of the request is the informative half, and a refusal is itself an answer.
How do you think about valuation for a company at our stage?
Why ask it
Opens the pricing conversation without committing you to a number. It also reveals whether they anchor on ownership targets, which constrains the round size more than the headline valuation does.
What would you need to see to move forward, and by when?
Why ask it
Converts interest into a testable condition. A specific request, such as two more months of retention data or a reference call with a customer, is a real process; general encouragement is not.
What questions do you still have that we have not covered?
Why ask it
Closing with this catches the doubt they were too polite to raise. It is also your last chance to correct a misunderstanding before they discuss you internally.
Running a first investor meeting
Practical guidance for the conversation itself
Before the meeting
- 1Read their recent investments and check whether they have backed a competitor. If they have, ask how they handle conflicts.
- 2Know your numbers without notes: revenue, growth rate, burn, runway, and unit economics.
- 3Decide the round size and what it buys, so you can answer the milestone question with specifics.
- 4Work out which two questions you must get answered if the meeting runs short, and ask them first.
- 5Agree internally who speaks to which topic if more than one founder is in the room.
Judging fit while you are in the room
- Did they read the material, or are they asking questions the deck already answered?
- Do they name specific portfolio companies and what they did for them, or speak only about their brand?
- Do they engage with the business, or steer everything back to market size?
- Are they clear about their own process and timeline, or evasive about who decides?
- Would you want this person on a call during your worst month?
After the meeting
Send what you promised within a day
Follow-up speed is one of the few signals an investor gets about how you operate. Send exactly what was asked for, no more, with the answer to anything you fumbled in the room.
Write down their conditions
Note the specific thing they said they needed to see. It gives you a concrete reason to come back to them, and it tells you whether their interest was real when you meet the condition.
Take references seriously
Call founders they did not introduce you to, including from companies that did not work out. This is the only part of diligence that runs in your direction, and it is worth the awkwardness.