The sale is the easy part: 4 questions to ask before a client sells

Accountants will field most of the tax questions this creates. The harder conversation is about what happens to the client, and the money, once the business is gone.

I’ve sold businesses of my own, and these days I sit on both sides of the table: buying private businesses, and managing the capital families are left with once they sell. From there, the pattern is hard to miss. The owners who handle life after the sale well start planning for it long before, and the person best placed to start that conversation is usually their accountant.

It tends to come down to four questions.

Is this client selling on someone else’s timeline?

The most exposed clients are usually the most self-sufficient: owners with nearly everything tied up in one asset that’s hard to divide, such as a business, a farm, or a long-held family trust.

When the business is the owner’s identity, the exit is easy to defer until something forces it. The warning signs are rarely dramatic, and they tend to look the same: no succession plan, no agreement between family members or partners on how proceeds will be split, and an owner who has run the business on instinct for decades.

When we look at buying a business, that last one is the first thing we test. If the relationships, the know-how, and the decisions all live in one person’s head, the business is worth less, and the deal takes longer.

Getting a business sale-ready, with the reporting a buyer will expect, typically takes six to 12 months. An owner who says “next year” probably has less runway than they think. Buyers can tell when the books were tidied up last month.

Add outside pressure, whether it’s a budget change, a personal health scare or an unsolicited offer, and the timeline stops being theirs. One in five owners planning to retire haven’t discussed it with anyone. Their accountant is often the only person close enough to see the pressure building.

What needs to be settled before the asset sells?

Three decisions need to be made before the sale: who controls the capital, how much of it stays liquid, and how competing family expectations get managed.

Most families haven’t talked any of this through, and that’s where transitions unravel. Research by US advisers Roy Williams and Vic Preisser attributes 60 per cent of failed wealth transfers to a breakdown of trust and communication inside the family. Tax, legal and every other cause combined account for just 15 per cent, so tax and structuring barely feature.

Control is the one most often missed. Will the proceeds sit with the founder, a spouse, a company, or a trust, and who has the final say?

Then liquidity: how much the family needs on hand before anyone starts talking about returns.

Fairness is the hardest of the three, because every sibling has their own version of it. In farming families, it’s increasingly common for the child who stays on the land to take 55 to 75 per cent of the farm, with the rest shared among the siblings who left.

Some of this sits outside an accountant’s remit. Raise it anyway. Left alone, it surfaces at the worst possible moment.

What happens in the first 90 days?

This is when the rushed, emotional decisions get made. Yale School of Management research of founders who had exited found just 20 per cent had planned for life after the sale, and 78 per cent said the reality differed from what they’d expected.

A founder who has spent decades with almost everything in one illiquid asset suddenly has cash, time, and a remarkable number of new friends. Be wary of the biggest smile and the sharpest suit in the room. The pitch to worry about is the polished one, the one that makes a newly liquid founder feel clever for saying yes.

The other instinct is to do what worked last time: back another business, a mate’s venture, a big property play. I understand the pull. Concentration builds wealth, and diversification keeps it. Most founders have spent their careers playing the first game, and few notice when the rules change.

I invest in private businesses for a living, so I’m no sceptic of illiquid assets. But a five-year lock-up can easily stretch to 10, and that matters when the family hasn’t yet worked out what the money is for.

My rule of thumb? Nothing irreversible in the first 90 days. Park the money somewhere boring and liquid, take the holiday, and let the adrenaline wear off before anything is committed.

Accountants can set that expectation well before settlement, while the client is still listening.

Where does the accountant fit once the business is gone?

For many accountants, the business was the relationship: the annual accounts and tax returns, BAS and payroll, forecasting, structuring, lender reporting, and often a seat at the table for the big calls. When the business goes, most of that work goes with it, and it’s easy to treat settlement as the end of the engagement.

That’s a mistake. Many of the post-sale decisions sit squarely in the accountant’s lane: how the proceeds are held, how investment income is taxed, how super fits now that Division 296 taxes earnings on balances above $3 million, and more heavily above $10 million, and how the estate is structured. The investment decisions sit alongside those, and both only work when they’re made together.

The accountant’s job is to stay at the centre of it: keep the tax and structuring work, bring in the right specialists, such as an estate lawyer and an investment manager, and make sure everyone is working to the same plan. The accountant who does that stays relevant to the next generation, too.

The same thinking applies before the sale. Plenty of good private businesses are better suited to a direct buyer than a broad sale process, where the owner keeps more say over timing and how the handover works. An accountant who knows who those buyers are is doing the client a real favour.

The part nobody prepares for

The 2027 changes will put more of these conversations on accountants’ desks, and most will start as tax questions.

I’ve watched too many people optimise an entire life around a number, hit it, and realise they’d built a machine for making money and forgotten to build a life to spend it in.

So, before the sale, someone needs to ask the client what the money is actually for. The answer shapes everything that follows, and the accountant is usually best placed to ask it first.

Josh Derrington is the managing director and chief investment officer of Alvia Asset Partners.