One of the proudest moments of my career was coaching a senior accountant through her transformation into a finance analyst. She was in her fifties when we started.
She worked at the Singapore affiliate of a Tokyo-listed pharmaceutical company, and she closed the books on time, every month, without fuss. Eighteen months later she was a finance analyst, sitting in meetings with the business and explaining the numbers instead of just reporting them.
She wasn't the only one. I ran the same transformation with whole finance teams across our ASEAN affiliates: Thailand, the Philippines, Indonesia, India, Vietnam, Malaysia and Singapore. Most of them were trained accountants with a strong accounting bias, which is exactly what their old job descriptions asked for. From the start of the project, it took us one to two years to get into the rhythm of forward-looking analysis instead of bean-counting.
So I can tell you two things with some confidence. Age isn't the hurdle. Mindset is, and mindset can be coached.
Gamers have a word for what I did: power-levelling. A newer player levels up fast by playing alongside a stronger one, taking on harder mobs and bosses than they could alone. That's the model. Your accountant works alongside someone who has done the job, on real-life problems, until they can do it without help.
This playbook is how I do it now in Singapore SMEs, with Claude doing a share of the heavy lifting that used to take a year of apprenticeship.
The Job Your Accountant Was Hired For Ends at the Close
In an earlier essay I wrote about the question your accountant can't answer: not what happened last month, but what should we do next. That gap is real. It's usually not a gap in intelligence, but a gap in the job description.
Most SME accountants were hired to keep the books, file on time and keep the auditors happy. The month ends, the numbers close, and the job is done. Nobody asked them to find out why the numbers are what they are, and nobody gave them the access or the authority to try.
What most founders don't know is that some of them have the aptitude to do far more. Call it a finance superpower. The question is whether you're willing to find out.
From Collator to Evaluator
The transformation I described above is the move from collator to evaluator.
A collator gathers the numbers. They chase each department for its budget, stitch the submissions together, and report what went up and what went down. It's necessary work, but on its own it adds very little value. Anyone with the spreadsheet can see that marketing went up.
An evaluator asks the next three questions:
- Why is this higher than last year? Not "because the submission said so", but the actual reason, from the person who owns the number.
- Why should we budget for this at all? Every cost line had a reason once. Is it still true?
- How does it improve the bottom line? If the spend goes ahead, what comes back, and when?
The difference shows up in meetings. At the MNC, the Regional HQ Executive Directors placed a premium on logic and understanding. A finance person who pointed out that a line had gone up 18% went back with more homework. A finance person who explained why it went up, what it would mean, and what the alternatives were got listened to, and in time got promoted. Within a year or two, my teams were the second kind, and they started adding value in rooms they used to sit quietly in.
A finance business partner is just an evaluator who has earned a seat in the conversation.
What Actually Took Two Years
Here's what surprised me. The hard part wasn't the spreadsheets.
Most accountants can learn VLOOKUP, XLOOKUP, SUMIFS and INDEX-MATCH, and build a forecast model, in weeks. With AI, I no longer see formula writing as a core skill, although you still need to understand what your AI tools write on your behalf. What took the most time was business partnering: going to colleagues in sales, marketing, medical and supply chain, and understanding the "why" behind the numbers. Not because their job was to collate and consolidate the budget, but because they genuinely needed to understand the business. And the most effective business partnering doesn't happen in scheduled meetings. It happens in the unstructured moments of the week: the pantry break, the networking session, the lunch.
To make matters worse, most accountants hit a wall on the way. I call it the chicken and the egg.
Finance needs the business to share the root causes, the technical reasons, the things that don't show up in a spreadsheet or a submission. But the business is reluctant to share "insider info" with someone who doesn't understand their business. A sales director won't explain the real reason a distributor is slipping to an accountant who, in their experience, only ever asks for the number by Friday. So finance stays in the dark, which keeps the business reluctant to share, which keeps finance in the dark. Chicken and egg.
Respect has to be earned before finance can get to the root of anything.
Two things broke the loop for us:
1. Top-down empowerment, especially from the CFO. Leadership made it clear that finance was expected in the conversation, not just at the end of it. That opened the front gate.
2. Training and coaching from senior finance people. FP&A leads, finance directors and the CFO sat alongside the team, modelled the questions, and gave feedback after each meeting. That's what opened the door.
Neither works on its own. Empowerment without coaching sends an unprepared person into a room they can't handle, and the door closes again. Coaching without empowerment trains someone for meetings they're never invited to.
What Changes in an SME
An SME has neither an FP&A team nor a CFO, so both halves of the solution have to come from somewhere else.
The top-down half comes from the founder. You're the one who tells the sales lead that your accountant will be asking why, and that you expect an answer, and some co-operation. It costs you one conversation, and nobody else can have it for you.
The coaching half comes from the fractional CFO. That's the senior finance person sitting alongside, on the days in the seat, doing what my FP&A leads and directors did at the MNC.
And part of the heavy lifting now goes to Claude. This is the genuinely new piece. When I trained teams at the MNC, a lot of the two years went on mechanics: learning Excel formulas and dashboarding, how a driver connects to a P&L line, writing the first draft of a variance commentary, working out which questions to ask before a meeting. Claude can now carry much of that. It can explain a concept as many times as it takes, without judgement and with unlimited patience. It can draft, so the accountant spends their time challenging a draft instead of staring at a blank page, which is a real problem for beginner analysts. It can play a sceptical sales director, so the first hard conversation isn't the real one.
Claude can shorten the transformation timeline, but it does nothing for the respect. That still has to be earned in person, one good question at a time.
Who Has the Aptitude
In Bookkeeper, Controller, or Fractional CFO? I argued that the difference between finance roles isn't skill, it's temperament. That still holds, and it's the first test here.
The signs I look for are about mindset, not age or qualifications:
- They ask why without being told to. When a number looks odd, they want to know, even if it reconciles.
- They're curious about the operations. They ask how the product is made, how the sales cycle works, why a customer pays late.
- They can live with being wrong. A forecast is always wrong in some way, or inaccurate, if you want a softer word. An evaluator is comfortable with that, and an accountant trained only on precision often isn't at first.
- They can explain a number to someone outside finance. Without jargon, in a sentence.
If the answers are no, that's not a failure. A superb accountant who loves a clean reconciliation is worth keeping exactly as they are, and pushing them into business partnering makes a talented person unhappy. Power-levelling is for the people who want to unlock a whole new set of skills and abilities.
The Ladder
Each rung is real work the business needs anyway, so nobody is doing exercises. The accountant climbs one rung at a time, and only moves up when the one below is routine.
1. Explain last month. Claude lists every line that moved against budget and last year, and drafts the "what". The accountant's job is the "why", and the only place to find it is the person who owns the number. This is the first time many accountants walk over to sales with a question instead of a deadline. What I check: did they talk to someone, or did they guess?
2. Own the cash. The weekly refresh of the 13-week cash forecast becomes theirs. Claude rolls it forward with the week's bank lines. They decide which receipts to believe, and they explain every miss against last week's forecast. What I check: is the miss explained by a real reason, or are you still talking about the numbers?
3. Interview the business. Before a budget or forecast meeting, Claude reads the numbers and prepares the questions worth asking. Then it plays the department head, the sceptical one, so the accountant can rehearse. Then they hold the real meeting. What I check: did they come back with a "canned" reason that explains a whole lot of nothing, or with a real insight we can use?
4. Challenge a line. This is the evaluator's question: why should we budget for this at all? Claude models what a cost line returns and what happens without it. The accountant makes the case to keep, cut or change it, to the person who owns the spend. What I check: does the logic connect to the bottom line, or is it merely descriptive?
5. Recommend. Claude drafts the one-page monthly pack and the options behind a decision, a hire or a price change. The accountant presents it to the founder and defends it. What I check: can they answer the second question? Anyone can answer the first.
How the Coaching Runs
The ladder is the what. The coaching is the how, and it happens on the seat days.
- Sit beside, then sit back. On the first pass at each rung, I do it with them. On the second, they lead and I watch. By the third, they do it and I review.
- Defend the number. Every review starts the same way: they explain a number to me as if I were the founder, and I keep asking why until they reach something they don't know. That's where the real lesson is.
- Claude as tutor. They can ask it to explain anything, as often as they like, and to quiz them before a meeting. It's patient in a way a busy senior rarely is, and there's no embarrassment in asking a basic question at eleven at night.
- They write the rules. The standing instructions in the Claude Project, the way we treat one-offs, how we name the forecast versions, are theirs to write and keep. Writing a rule down is how you learn it.
- Feedback after every meeting. Five minutes, the same day: what landed, what didn't, and what to ask next time. Giving timely feedback was the single most useful habit at the MNC, and it hasn't changed.
What I Don't Let Claude Do
The same line holds here as in the budget and the cash forecast: Claude can inform the work, but it doesn't own any of it.
1. Hold the conversation with the business. Claude can prepare it and rehearse it. It can't earn respect, and respect is the whole point of rung three.
2. Decide who is ready. Whether someone has the aptitude, and when they're ready for the next rung, is a judgement about a person. That's mine, with the founder.
3. Sign the commentary. Nothing goes to the founder that the accountant can't explain without the draft in front of them. If they can't, it isn't theirs yet.
4. Replace the coaching. A model can explain a concept. It can't tell someone after a tense meeting that they handled the pushback well, or that they should have asked one more question, more assertively. That feedback is what changes behaviour.
What the Founder Gets
- A finance function that keeps running. When the fractional seat steps back, the forecast, the pack and the questions don't leave with it.
- More out of each seat day. The more the accountant carries, the more of my one or two days goes to the decisions only a CFO-level view can help with.
- A reason for a good person to stay. A career path from accountant to analyst to business partner is worth more to some people than a raise. That matters at the size where, as I wrote in When Should a Singapore SME Build Its Finance Team?, each finance hire is a big decision.
Where This Breaks
- The mindset isn't there. You can coach a mindset that's curious but untrained. You can't coach one that doesn't want to change. If rung one is still a struggle after a few months, stop, and keep a good accountant as a good accountant.
- They're buried in bookkeeping. Nobody evaluates anything while drowning in data entry. Free the time first; I've written about what to automate first.
- The founder bypasses them. If department heads can go straight to you and skip finance, they will, and the chicken-and-egg loop never breaks. The top-down half isn't optional.
- The accounting is outsourced. An external firm's accountant can learn rungs one and two, but they aren't in the building when the reasons are discussed. If you want a business partner, at some point you need someone in-house.
Three Checks for This Month
1. Ask your accountant why one number moved. Pick a line that changed last month. Don't ask what it was. Ask why.
2. Watch what they do next. Do they guess, or do they go and find out? That's the aptitude test, and it costs you nothing.
3. Invite them to one meeting. A sales or operations review they'd normally only see the minutes of. Tell the room why they're there.
The question your accountant can't answer is often a question nobody has ever asked them. Ask it, back them up, and coach the answer. Age isn't the hurdle. Mindset is.
Tested on Claude, October 2026.