Skip anything you could read on the website and anything about hours or team socials. Ask about the metrics this type of business is judged on, the cash position and the next raise, where the founder and board want to take it, the state of the books today, and what success looks like in the first three months. Have three to five specific questions ready and ask them during the conversation, not only at the end.
Why your questions carry as much weight as your answers
At senior level, what the interviewer is trying to find out is whether you understand their business.
This is advice I give to everyone I put forward: asking good questions is just as important, if not more than having good answers. While they are answering, you are not talking, and one sharp question about their market says more about your capability than a long spiel about your own experience.
Founders notice when it is missing. On a search I was running for a founder in March 2026, the interviews that went badly were the ones where candidates asked surface-level questions. As much as he was trying to understand them, they needed to understand the business too. Early in 2026, on a CFO search, the reason one candidate stood out for the founder was the questions: he told me they had asked the best ones, so he wanted to meet them again. Within reason, though. If you are pummelling the interviewer with questions, take a step back. It is a balance.
The people I prepare for these interviews are going for a first head of finance or first CFO seat in an Australian venture-backed tech, fintech or deep tech company, so every example below is written for that interview.
The surface-level questions to drop
A surface-level question is one the interviewer could answer for any candidate in any company. What is the team like? What are the working hours? Steer clear of those, and of transactional questions in general.
Generic finance questions fall into the same trap. Asking about profit or margin shows you know what a P&L is. Researching the specific metrics a business like theirs is judged on, and asking about those, shows you understand that type of business.
| Surface-level question | Question that shows you get the business | |
|---|---|---|
| Performance | What are your margins like? | Which metrics does the board look at first, and how have they moved this year? |
| Cash | Is the company doing well? | How many months of runway are there, and what happens if the next raise slips? |
| Team | What is the team like? | Who does the close today, how long does it take, and what breaks? |
| The role | What are the working hours? | What do I need to do in the first three months to be successful? |
Questions that test the business and its runway
These questions show you can read a business the way an investor does. I draw a line between a company that is unprofitable but growing fast and putting the money back into scale, and one that is unprofitable without growing at a significant rate. The first is fine, because the money is going back into the business. The second is another discussion, and you want to know which one you are joining before you sign. In 2024 I wrote that candidates should ask founders about growth plans over three, five or ten years and about recent products or revenue streams. That still holds. Make the questions specific:
- Which two or three metrics does the board look at first each month, and how have they moved this year?
- How many months of runway are there at the current burn rate, and what is the plan if the next raise takes six months longer than expected?
- Where is growth coming from now, and which revenue line do you expect to matter most in two years?
- How are you dealing with cost of capital, or with the revenue recognition problems that usually catch out a business like this?
The last one is the kind I push candidates towards. If you have worked in that style of business before, you know the classic catches, and a question about one of them tells the interviewer you already get their world.
Questions for the founder and the board
Anyone moving from an established ASX business into a startup should treat buying into the founder's vision and plans as the deciding factor, because you are investing in the leader, not just the product. The chemistry and working style between the finance leader and the person they report to are critically important too.
You will often meet more than the founder. On one CFO search in 2026 the plan was for candidates to meet the chair of the board and other executives as well as the CEO. Use each meeting to ask what that person needs from finance.
- What do you want the business to look like when this round of capital runs out?
- Who is on the cap table, and what does each main investor expect in terms of timing and exit?
- What questions does the board ask that you cannot answer today?
- Which decisions do you want a finance view on before you make them, and which ones will stay with you?
On a search in 2026, the founder was keen to take advice from an incoming CFO on where the best value for the company was. You want to know early whether you are being hired for that, or to keep the books.
Questions about the finance function you would inherit
Many first finance roles exist because the processes are not clean yet. Expect manual work and a lot of it, because fixing it is the job. Your questions should find out how far from clean it is.
- Who does the bookkeeping, payroll and month-end today, and how many days does the close take?
- Which systems hold the numbers, and how does the board pack get built each month?
- What does the founder know is broken in finance, and what has already been tried?
- Has an auditor or investor raised anything in the last year that is still open?
The other side of the table: the financial acumen questions interviewers ask and what a strong answer sounds like.
Questions about the role and its next 24 months
Two of the best questions are also the simplest: what do the next twelve months look like for the business, and what do I need to do in the first three months to be successful? The answers tell you whether the founder has thought past the hire, and they give you the first draft of your plan if you get the job.
Then ask how the role changes. On a call about one senior finance role in July 2026, the plan was six months hands-on, lifting the maturity and robustness of the finance processes, then a move into financial strategy and commercial leadership. You should know whether a path like that is the one on offer.
- What would make you say in a year's time that this hire worked?
- Do you expect this role to become the CFO, or will you hire above it after the next round?
- When will the function need a second hire, and who decides that?
- How is the package split between base, short-term incentive and equity, and what does the equity look like at today's valuation?
What to do once you are in the seat: a CFO's first 90 days, month by month.
How to ask them
Prepare three to five questions that go into the specifics of the business, using its terminology and technical language where it fits. Ask them after you have heard what the founder is trying to fix, build or create, because that context is what lets you probe the real technical, regulatory or operational challenge.
Do not save them for the end. A good interview flows like a chat: they ask a question, you answer, you ask one back. If the interview is on video, keep your questions on the screen in front of you. The interviewer will never see your notes.
It also helps to know what the founder will be testing. I wrote up how founders should interview a finance director, stage by stage. Read it before your first conversation and you will know what the other side wants to hear.
Before you ask about equity, read how stock options work in an Australian startup.
Common questions
What questions should I ask at the end of a finance job interview?
Ask about the metrics the business is judged on, the cash position and the next raise, what the founder and board want from finance, the state of the finance function today, and what success looks like in the first three months. Better still, ask some of them during the interview rather than saving them all for the end.
How many questions should I prepare for a finance interview?
Prepare three to five specific questions about the business, its metrics and its known challenges, using the right terminology. That is enough to show you understand the business without turning the interview into an interrogation.
What questions should I avoid asking in a finance interview?
Avoid surface-level and transactional questions such as what the team is like or what the working hours are, and anything you could answer from the company's website. Generic questions about profit or margin also add little; ask about the specific metrics that type of business is judged on instead.
What should I ask a startup founder in a CFO or head of finance interview?
Ask where they want the business to be when the current capital runs out, who is on the cap table and what those investors expect, what the board asks that they cannot answer yet, and which decisions they want a finance view on. Those answers tell you whether you are being hired to advise or to keep the books.
Why do the questions a candidate asks matter so much in a finance interview?
At senior level the interviewer is looking for understanding of their business. A specific question about a metric or a known industry problem shows that understanding faster than describing your own experience, and it tells you what you would be walking into.
These guides set out how we see it, drawn from the searches we run and the finance leaders we work with. They are general information about the market, not financial, accounting or legal advice, and they are no substitute for advice on your own circumstances.