Questions to Ask Investors in a First Meeting
For founders working out what questions to ask investors when a first meeting is on the calendar, from pre-seed through Series A. The 55 questions follow the meeting's own order: fit, how the fund works, what they do after the cheque clears, how they behave when a company struggles, and next steps. The questions to ask an angel investor sit straight after the fund ones, to swap in when the person across the table is spending their own money and not a venture fund's.
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The questions
Each question, and why to ask it
Fit
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.
Are we inside what you usually back, by stage and sector, or at the edge of it?
Why ask it
Funds do take meetings outside their usual mandate, to learn a market or to keep a relationship warm. If you sit at the edge of theirs, expect a slower process and a partner who needs more evidence to argue for you.
Would you be the person working with us after an investment, or would someone else at the firm take over?
Why ask it
The partner who wins the deal is sometimes not the one who joins the board. Meet whoever you would actually be calling before you treat the firm as a fit.
Which companies in your portfolio sit closest to what we do, and would any of them see us as a competitor?
Why ask it
Ask before you share detailed numbers or a roadmap. An investor with a stake in a rival should be able to say exactly who would and would not see your material.
What is the most common reason you pass on companies like ours?
Why ask it
They hand you their standard objection before it is applied to you. If the reason is one you cannot change, such as market size or geography, you have saved both sides a month.
What is your investment thesis right now, and has it shifted in the last couple of years?
Why ask it
A thesis that moved recently shows what the partnership is arguing about this quarter. If you match the old thesis and not the new one, expect polite interest and a slow no.
What have you learned from the companies in our market that you backed or passed on?
Why ask it
You find out how much homework they have already done, and whether an old disappointment is colouring how they see you. An investor who lost money on a similar idea needs a different pitch from one meeting the category for the first time.
What do you look for in founders at our stage that a deck cannot show you?
Why ask it
At pre-seed and seed there is little data, so the answer is usually about you. Whatever they name, such as speed, candour or knowledge of the customer, is what they will be testing for the rest of the meeting.
The fund
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.
What ownership do you aim for in a first investment?
Why ask it
A fund that needs a fixed share of the company will size the round around that share, whatever amount you asked for. Hearing the target early tells you whether two such investors could even fit in one round.
Where are you in the life of the fund, and how much is left to deploy?
Why ask it
A fund near the end of its investing period may have little set aside for later rounds and more interest in when you exit. One that has only just closed has years in hand and money held back, which makes it a different partner to have.
How many new investments do you make in a year, and how many boards do you sit on yourself?
Why ask it
This is arithmetic about attention. A partner with a dozen boards and a busy year of new deals has limited hours for each company, whatever the website says about support.
How do you approach follow-on funding in later rounds?
Why ask it
Reserve policy decides whether they can back you again. The cases where they sat a round out matter most, because new investors tend to read an insider's absence as a verdict, whatever the real reason.
Who are your own investors, and does anything in your fund's rules limit what you can back?
Why ask it
Venture capitalists answer to the people whose money they manage, and some funds carry limits on sectors, countries or deal structures. Better to learn about a restriction now than in the final week of a round.
How big would we need to become for this investment to count as a success for your fund?
Why ask it
The size of the fund shapes the outcome they need from you. If a sale that would change your life barely registers for them, you will feel that pressure in every strategy conversation.
At this stage, do you invest through a priced round, a SAFE or a convertible note?
Why ask it
Each instrument treats valuation, dilution and investor rights differently, and the common ones vary by country. Note their preference, then have a startup lawyer explain what it would mean where your company is incorporated.
Does the amount we are raising look right to you for what we plan to do with it?
Why ask it
An investor who sees rounds at your stage every week can say whether the figure reads as too thin to reach the next milestone or too large for the progress so far. Take it as one opinion to set beside the others, and do not resize the round in the room.
How do you think about valuation for a company at our stage?
Why ask it
It opens the pricing conversation without you naming a number first. Listen for whether they reason from comparable rounds, from your traction or from the stake they want to end up with.
If you led the round, would you help fill the rest of it, and who would you bring in?
Why ask it
Some leads set the terms and leave you to find the remaining money, and others pick up the phone. The names they mention also tell you which investors trust their judgement.
Angels
How many angel investments have you made, and how many do you make in a typical year?
Why ask it
A practised angel has seen the paperwork before and knows how long these companies take. A first-time angel can be a fine backer, though you should plan to spend more time explaining the process and the risk.
What size of cheque do you usually write, and is that what you have in mind here?
Why ask it
Angel cheques run from token amounts to sums that could anchor a small round, and a job title is no guide to which. With the figure in hand you can count how many more conversations like this one the round needs.
Are you investing your own money directly, or through a syndicate or an angel group?
Why ask it
The answer changes who decides and how the investment shows up on your cap table. With a group, ask who leads, how members vote and whether everyone comes in through a single vehicle.
Can you commit on your own, or do you wait for a lead investor to set the terms?
Why ask it
Plenty of angels like a company and still will not move until someone else prices the round. Knowing that tells you whether this conversation can start the round or only help finish it.
What from your own career would be most useful to us, and how much time could you give each month?
Why ask it
An angel investor's value is usually one specific thing: an industry they know, a job they have done, or the people who return their calls. A number of hours is harder to inflate than a promise to be available.
Would you want an advisory role or extra equity for helping, or is the investment the whole arrangement?
Why ask it
Settle this before any money moves. An angel who assumes advisory shares on top of the cheque and a founder who assumes free help are heading for an awkward call.
If we raise from a venture fund later, would you want to invest again or are you comfortable being diluted?
Why ask it
Many angels write one cheque and stop, which is fine as long as nobody is surprised. If they want a right to invest in later rounds, ask a lawyer how that is usually handled for small holdings where you are.
How long are you prepared to wait for a return, and could you live with losing the whole amount?
Why ask it
Shares in a young company can stay unsellable for many years and may end up worth nothing. Someone investing savings they might need back will be a more anxious reader of every difficult update.
Do you count as an accredited investor, or the equivalent under the rules where you live?
Why ask it
The name for this and the test behind it change from country to country, and some places have neither. Check with your lawyer what you need to confirm, and keep on file, before you accept anyone's money.
Which other angels would you introduce us to, whether or not you invest yourself?
Why ask it
Angel rounds tend to fill through people vouching for each other. An introduction offered even after a no tells you the meeting went better than the answer suggests.
Working together
Beyond capital, what do you actually do for portfolio companies?
Why ask it
Named things count here: recruiting help, customer introductions, a specific operating partner. A general claim about being hands-on often turns out to 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.
Which introductions could you make in our first ninety days, to customers, hires or later investors?
Why ask it
Asking for a time frame and a category turns a vague promise of a network into something you can check. Write the names down and see whether they come up again after the meeting.
How often do you speak to your founders between board meetings?
Why ask it
An investor who texts every week and one who surfaces once a quarter can both be good to have. Which of the two you would rather live with is worth settling before the money arrives.
How involved do you want to be in strategic and hiring decisions?
Why ask it
A mismatch here is a common source of friction on a board, whether you wanted more of a sounding board or less of one. Ask for one decision at a portfolio company where they pushed and one where they stayed out.
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.
What reporting and communication would you expect from us?
Why ask it
A written update every month is a common ask and cheap to give. Weekly calls, ad hoc data requests or dashboard access cost real hours, and they are easier to negotiate before a term sheet than after.
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.
How do you help when it is time to raise the next round?
Why ask it
The strongest answers name the funds they would call and when they would start. The harder half is what they would tell those funds if they were not investing again themselves.
Hard times
What happens when one of your companies misses plan or has to pivot?
Why ask it
This question describes your worst quarter in advance. Look for a specific story with a founder still in the seat, not a statement about backing people.
What was the last real disagreement you had with a founder, and how did it end?
Why ask it
Every working relationship between a founder and an investor has one. An investor who cannot recall a disagreement is either new to investing or not being candid, and both are worth probing.
How would you want to hear bad news from us: a call that day, or in the next update?
Why ask it
Nearly everyone says they want it at once, so ask about the last time a founder did exactly that. How that call went is the real answer.
Have you backed a bridge round for a company that was running short of cash, and how did you decide?
Why ask it
A bridge is where support gets expensive for the investor. You are listening for the test they applied, and for whether the terms they offered were ones the founder could live with.
Have you ever been part of replacing a founder or chief executive, and what led to it?
Why ask it
A yes is not disqualifying, since boards sometimes have to act. Pay attention to how early the founder knew there was a problem and whether they were given a chance to fix it.
What happens to a company you backed if the partner who led the deal leaves the firm?
Why ask it
Companies can end up with a board member who did not choose them and has no stake in the original decision. A firm with a handover habit will be able to describe it.
How do you respond when a founder gets an acquisition offer that is good for them but small for the fund?
Why ask it
Here your interests and theirs can pull apart. Ask how they voted the last time it happened, and have a lawyer explain which investor rights could block a sale under the terms they usually ask for.
Which of your founders could we 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.
Next steps
What is your biggest concern about our business as you have heard it today?
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 would you need to see to move forward, and by when?
Why ask it
It turns interest into a condition you can test. 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 does your decision process look like, and who else has to say yes?
Why ask it
How many partner meetings there are, whether the partners must all agree and whether a committee signs off will set your timeline between them. 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 diligence would you want to do, and what should we have ready?
Why ask it
A list of documents, customer calls and references lets you prepare a data room once instead of answering requests one at a time. It also shows how deep they go at your stage, which varies a great deal from firm to firm.
Are there terms you always ask for that we should know about before a term sheet arrives?
Why ask it
Board seats, rights to invest in later rounds and preferences on a sale are easier to discuss as habits than as clauses already on paper. What each term means differs by country, so take the list to a lawyer before you respond.
If you decide this is not for you, will you tell us plainly and say why?
Why ask it
The costly outcome in fundraising is the slow maybe that never becomes an answer. A promise of a clear no, with a reason, makes it easier to chase one later without sounding impatient.
If the timing is wrong for you now, how should we keep you informed?
Why ask it
Interest that is not ready yet can be kept warm with a short monthly update. Agreeing the format now means the next message from you is expected and not a cold follow-up.
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.
- 4Mark the three questions you must get answered even if the meeting runs short, so you are not choosing under pressure with ten minutes left.
- 5Agree internally who speaks to which topic if more than one founder is in the room.
Which questions to take into the room
Questions to ask a VC
Start with Fit and The fund. A venture capitalist invests other people's money on a schedule, so cheque size, ownership target and the age of the fund decide whether a deal is possible at all, before any question about help matters.
Questions to ask an angel investor
Swap The fund for the Angels group. An angel is spending personal money and personal time, so you need to know how they decide, what they know that you do not, and whether they can sit calmly through the years a young company takes.
When the investor runs the clock
If you are left ten minutes at the end, ask three things: one question from Fit, one from Hard times, and what they would need to see to move forward. Everything else can wait for a second meeting or a partner call.
What to hold back in a first meeting
Valuation, standard terms and diligence lists land better once the investor has shown interest. Raised in the opening minutes they sound like negotiating before there is anything to negotiate.
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. Along with the questions you asked in the room, this is the diligence that runs in your direction, and it is worth the awkwardness.