To assess a CFO or head of finance, test startup fit and level before technical skill: a two-way first conversation, a case study built on a real finance problem in your business, then a culture stage with the founder, and references taken only with the candidate’s permission.
What founders actually find hard about this hire
Most interview guides assume the problem is knowing which technical questions to ask. The founders in our network say otherwise. In our Q3 2026 poll we asked founders what the hardest part of hiring their first internal finance person is. Finding someone who fits a startup took 38.8% of the vote and knowing what level to hire took 30.6%. Assessing their technical skill came last, at 11.2%.[1]
| Share of the vote | What it means for how you interview | |
|---|---|---|
| Finding startup fit | 38.8% | Test for building without structure, in every stage. This is the question the interview has to answer. |
| What level to hire | 30.6% | Decide it in the brief, before anyone is interviewed, then assess against the seat rather than candidate against candidate. |
| Affording the hire | 19.4% | Usually a symptom of the level question. A clear brief makes the budget conversation much easier. |
| Assessing their skill | 11.2% | Test it once, properly, with a case study and a finance person you trust marking it. |
That matches what I see in the searches I run. A non-finance founder worries that they cannot judge a reconciliation, but that is rarely where these hires go wrong. They go wrong because someone excellent in a large, structured finance team walks into a 30-person business with no processes, or because the business hired a CFO for what was really a head of finance job. Technical depth still matters, and the case study below tests it. But as I said on Celia’s Corner, the thing founders ask me for most often is communication, because “technical skill set is no longer the moat or the weapon that people think it is anymore” now that AI can produce a lot of the figures. So build the interview around fit and level, and treat the questions as tools for testing those two.
Settle the level before the first interview
Level is the question behind 30.6% of that vote, and it cannot be answered in an interview room. It is decided when you write the brief. A financial controller, a head of finance and a CFO are different jobs. The way I describe the first two: “financial controller is more around as in the name, financial controls and compliance and reporting, where a head of finance is probably going to be a little bit more broadly across the forward-looking tasks”, meaning modelling, budgeting and forecasting. A CFO sits above both and owns capital, investors and the numbers behind the strategy.
The mistake I see most is pricing the role against the business as it is today rather than as it will be in 12 months. The founder hires for current complexity, the business outgrows the person, and a year later they are running the search again. The opposite mistake exists too: a CFO title on a job that is really month-end, reporting and cash. Decide which seat you are filling for the next 18 months, write that down, and assess every candidate against it rather than against each other.
One test of whether you have the level right comes from the other side of the table. If a founder expects a financial controller to do all the bookkeeping personally with no support, that is a red flag about the founder. It usually means they do not yet understand what a controller does, or the business is not ready to hire at that level. Good candidates spot it in the first conversation.
If you are still choosing between the seats, I set out which finance seat fits which stage, with what each one owns.
Stage one: the first conversation, run both ways
I run senior finance processes in three stages, and the first is a get-to-know-you conversation that works as information gathering in both directions. You are learning how they think. They are deciding whether your business is one they could build in. Treat it as a two-way conversation rather than a screening call, because the best candidates are assessing you just as hard.
Listen more to the questions they ask than to the answers they give. I have seen technically strong CFO candidates dropped from a process because they did not ask strong enough questions. Someone who is going to run your finance function should want to know about runway, unit economics and what the board is worried about before you have finished describing the role. In the First Finance Hire Playbook I list the first-conversation signals I rely on: a strong candidate asks smart questions about your business model, and a weak one talks process and systems before understanding the business, or never asks about runway at all.
| How to test it in stage one | What a good answer sounds like | |
|---|---|---|
| Curiosity about the business | Describe the business briefly, then stop. Note what they ask before you get to the role. | Questions about runway, the business model and what the board is worried about, unprompted. Silence, or questions only about title and reporting line, is the warning. |
| Built or inherited | Ask them to walk you through the finance function they left behind and what it looked like when they arrived. | A clear before and after they created, with the order they did it in and what they chose not to fix. |
| Level | Share what the next 18 months look like: the raise, the headcount, the board. Ask which parts they would own personally. | A realistic split between hands-on work now and building towards a team, pitched at the seat you wrote down. |
Stage two: a case study built on a problem you actually have
The second stage is where technical skill gets tested, and the rule is simple: base it on a common finance problem in your own business, not a generic exercise. A month-end close that takes twelve days, a forecast nobody outside finance believes, an R&D claim that has never been properly documented, or a hiring plan the board has not stress-tested. For many finance functions a 12-day close comes down to manual data pulls from three systems, reconciliation in Excel and reformatting for board reports. Ask a candidate to diagnose that and you learn more than any question about accounting standards.
What you are marking is not the output. In a case study it is rarely the production of the task that decides it. It is the questions they ask, the assumptions they make and state, and how they answer when you push on them. A candidate who hands back a polished model built on assumptions they never checked with you has shown you exactly how they will work.
If you are not a finance person yourself, do not mark it alone. Many founders already have an outsourced fractional or virtual CFO, and this is one of the most useful things that person can do. As I put it on Celia’s Corner, before someone hires in finance “they might have an external party that they hire as like an outsourced fractional CFO or a virtual CFO”, and they can bring them into the process as “a final stage sort of sense check interview where they can qualify whether they’re the right fit for the role technically.” A trusted accountant or a finance leader from your board or investor network works too.
| The question or task | What a strong answer sounds like | |
|---|---|---|
| Your close takes twelve days. Diagnose it. | Tests diagnosis and prioritisation, not recall of accounting standards. | Asks which systems the data comes from and how much is manual before proposing anything, and names the one fix they would make first. |
| What does this hire plan do to our runway, and what if revenue lands a quarter late? | Tests whether they will test you, which is the value of the role. | Says yes with a trade-off, or not yet with a reason, and names the assumptions that have to hold. Agreeing with the plan is the wrong answer. |
| Explain our unit economics back to me. | Tests whether they have understood your business in the time they have had with it. | A clear, plain-English read of how you make money and where the margin goes. Not being able to do it after half an hour is a red flag in the Playbook. |
| Where would you use AI in this function, and where not? | Tests judgement about accuracy and accountability. | AI does the first pass on reconciliations, analysis and a first forecast. A qualified person checks every number that reaches a board, investor or auditor. |
| What part of this role would you do yourself in month one? | Tests whether their picture of the job matches yours. | Specific hands-on work, with an outsourced bookkeeper doing the transactional layer. An answer made only of delegation describes a different job. |
One more thing on technical rounds: watch your own bias. The Australian market carries a bias towards recent local experience that is rarely discussed openly, and it discards real capability.[2] If someone has run finance in a more complex market, test whether the experience transfers, not whether they know the local form of something they have done at ten times the scale.
Stage three: culture, with the founder in the room
The third stage is about fit, and it is not a formality. In an early stage business the culture fit, the team fit and the personality fit matter as much as the technical work, because the job is dealing with pace, ambiguity and the absence of a playbook. People who have only worked in established businesses often underestimate how relentless that is. I usually run this stage as a coffee with the founder rather than another panel, because a coffee tells you things a competency matrix cannot.
Do not use this stage to rule out corporate backgrounds. There is a myth in startup land that your first finance hire has to come from a startup, and it cuts out a large pool of capable people. A corporate background does not stop someone building from scratch. Often it means they have seen what good looks like and know exactly what they are trying to build. What marks out the best first hires is how they think without a playbook, not how big their last employer was. Our own data points the same way. Of the 191 first finance hires we traced at funded Australian startups, 46 came from another startup or tech company and 8 came straight from a Big 4 firm. The other 137 arrived from corporates, private businesses, advisory firms, banks and elsewhere. That study only sees companies that eventually built an internal finance function, and a fractional or outsourced vCFO does not show up in public data at all.
What you are testing for is whether they have built, or only inherited. The strongest signal in the Playbook is someone who has built a finance function from scratch, not just taken over one that worked. The clearest warning is big-company experience with no evidence of adaptability, problem-solving or initiative. Chemistry sits alongside both. My advice to senior candidates is never to ignore discomfort with a CEO’s communication, decision-making or energy in an interview, because at this level it only intensifies in the role. The same applies to you. If something feels off in the third stage, it will not improve in month four.
Remember that stage three is also where they decide about you. In the same Q3 poll, finance leaders in our network rated a clear vision as the most attractive founder trait (46.9%), well ahead of being financially literate (7.1%). You do not need to out-finance the candidate. You need to be clear about where the business is going.
Reference checks: ask first, then ask the right people
Always check with the candidate before you contact anyone. I have seen it go badly when a reference call found its way back to a candidate’s current employer, and at senior level that can cost someone their job before they have accepted yours. Agree the names and the timing with them, and take references at the end, not as a screening step.
Then look at who the referees are. One of the green flags in the Playbook is references who are founders and CEOs, not just other finance people, because a CEO can tell you whether the numbers changed decisions, which is the job. Confidence shows here too: in one CFO search, the candidate who stood out was the only one to volunteer referees unprompted, before I had asked. And references do change outcomes. I have had a CFO process run two months longer than planned, first because diaries on both sides were full, then because the preferred candidate failed a numeracy test at the final stage and the references were not glowing.
| Who to ask, and what | What you are listening for | |
|---|---|---|
| Before any call | Ask the candidate for names and permission, and agree when you will call. | Referees offered readily are a good sign. Agreeing the timing protects them, and you, from a call reaching their current employer early. |
| A founder or CEO they worked for | What did finance look like when they arrived, and when they left? Which decisions changed because of their numbers? | A function they built rather than maintained, and specific decisions the CEO made differently because of them. |
| A peer outside finance | How did they work with sales, product or operations when the numbers said no? | Someone who explained the trade-off and found a way through, rather than a blocker or a pushover. |
Psychometric testing is optional. It is not standard in these processes, every business has its own view and tools, and I leave the decision to the client. If you use one, use it as one input at the end, not as a filter that decides the shortlist.
Two strong finalists: how to decide
If you reach the end with two people you would happily hire, go back to the level you wrote down before the first interview. Pick the one built for the business you will be in 12 to 24 months from now, not the one who would be most comfortable in the business you are today. If they are genuinely level on that, pick the one who asked the better questions in the case study, because that is the behaviour you will live with every week.
Then move. The people you are choosing between are scarce. As I said on Celia’s Corner, a first finance hire or first CFO who has done it before, scaled a business and “wants to go back in and do it again, is much rarer than people realise.” Senior finance candidates often have more than one process running, and a slow decision is how founders lose both finalists. The offer stage is its own job, and I cover it in how to close a finance hire, from the offer to the counter-offer. For the end-to-end process around these stages, from the brief to the start date, see how to hire a CFO in Australia.
Once they have signed, judge the hire on the right things. I set out what a finance leader’s first 90 days should produce, from the founder’s side as well as theirs.
Common questions
What are the best CFO interview questions for a startup?
Questions that test fit and level rather than technical recall. Ask them to explain your unit economics back to you, to say what your hire plan does to runway if revenue lands a quarter late, to diagnose a real problem such as a twelve-day month-end close, and to describe what the finance function looked like when they arrived at their last business and when they left. Listen to the questions they ask as much as the answers: technically strong CFO candidates get dropped for not asking good enough questions.
How many interview stages should a CFO or head of finance process have?
Three is enough: a two-way get-to-know-you conversation, a case study built on a real finance problem in your business, and a culture stage with the founder, then references. Senior finance candidates often have more than one process running, so a long, slow process is a common way to lose the finalist you wanted.
How do I assess a finance candidate if I am not a finance person?
Get someone technical to mark the case study. Many founders already use an outsourced fractional or virtual CFO, and they can join the case study or a final sense-check interview to qualify whether the candidate is right technically. A trusted accountant or a finance leader from your board or investor network also works. Your own job is to judge fit, level and how they think, which you are well placed to do.
Should I rule out candidates from a corporate or Big 4 background?
No. The idea that a first finance hire must come from a startup is a myth, and it cuts out a large pool of capable people. A corporate background often means they have seen what good looks like. What to test for is whether they have built something without structure, and whether they show adaptability, problem-solving and initiative. Big-company experience with none of those is the real red flag.
What do founders find hardest about hiring their first finance person?
Fit and level, not skill. In Story Recruitment's Q3 2026 poll of its network, finding someone who fits a startup took 38.8% of founders' votes and knowing what level to hire took 30.6%, while assessing technical skill took 11.2%. The poll covers Tom Hunter's own network of founders, CFOs and senior finance people, with over 260 votes across four questions, and does not publish n per question.
References
- Our Q3 2026 State of the Market report polled the Story network of founders, CFOs and senior finance professionals, with over 260 votes across four polls. It is our own network, not a random sample of Australian founders, and the report does not publish n for each question. Figures here are read from the report’s chart.
- Something I see and rarely hear discussed: the Australian market carries a bias towards recent local experience, and undervalues significant international careers, including candidates who have run larger and more complex finance functions overseas.
These guides set out how we see it, drawn from the searches we run and the finance leaders we place. They are general information about the market, not financial, accounting or legal advice, and they are no substitute for advice on your own circumstances.