If you’re buying a business, there’s a question you should be asking the seller early on, and frankly, most buyers don’t. It’s simple, almost innocent on the surface, but it tells you more about the deal than half the due diligence pack ever will. That question is: when did you start planning to sell?
Most buyers obsess over revenue, profit, add-backs and forecasts. All of that matters, but none of it exists in a vacuum. Numbers don’t just appear, they’re shaped over time. And in the real world, sellers and their accountants typically need around three years to properly prepare a business for sale if the goal is to maximise value. That preparation changes behaviour, reporting, structure and sometimes reality itself.
Think of it like selling a house. Nobody lists their home and then starts decorating. They repaint, declutter, fix the leaky taps and tidy the garden before the “For Sale” sign goes up. Businesses are no different. Except instead of paint and furniture, the tools are accounting treatments, timing decisions, cost allocations, and sometimes very creative explanations.
When a seller tells you they started planning to sell three years ago, what they’re really saying is that the last three years of numbers have likely been produced with a buyer in mind. Expenses get reclassified. Owner costs get stripped out aggressively. One-off costs suddenly become “non-recurring”. Revenue recognition gets tidied up. Risky clients quietly disappear. Systems are tightened, sometimes hurriedly, sometimes superficially.
None of this is illegal. Much of it is entirely legitimate. But it does mean the business you’re analysing is not a neutral snapshot of day-to-day trading. It’s a business that has been groomed to look attractive. Polished. Optimised. Presented.
From a buyer’s perspective, that polish cuts both ways. On the one hand, a well-prepared business can be easier to take over. Processes might be documented, management accounts cleaner, and compliance tighter. On the other hand, you’re paying for the result of that preparation. You’re buying at the peak of intentional performance, not necessarily sustainable performance.
This is why, counterintuitively, it can be in your best interest if the seller hasn’t been planning to sell for long, or at all. A business that comes to market unexpectedly, due to burnout, illness, a change in priorities or an external opportunity, is often a far more honest reflection of how it actually operates. The numbers are messier, yes, but they’re also more real. You’re seeing the house before it’s been staged.
That doesn’t mean you should avoid prepared sellers. It means you should understand what you’re looking at. If a seller has spent three years getting ready, your job as a buyer is to reverse-engineer that preparation. Ask what changed during that period. Ask which costs were removed and why. Ask what the business looked like before “sale mode” kicked in. Ask what would happen if those optimisations stopped.
The timing of a seller’s decision to sell also tells you something about motivation. Someone who has been planning for years is often very price-driven. They’ve invested time, money and effort into achieving a particular valuation. They’re emotionally anchored to it. Someone who is selling sooner than expected is often more flexible, more pragmatic and more focused on certainty than squeezing every last pound out of the deal.
So ask the question. Not as an accusation, not as a trap, but as a genuine point of curiosity. When did you start planning to sell? Listen carefully to the answer. The words matter, but the hesitation, confidence and detail matter more.
Because in business acquisitions, just like in property, it’s not just about what you see on viewing day. It’s about what the place looked like before the fresh coat of paint went on, and whether you’re paying for the walls, or the illusion.
Please seek professional advice and guidance when considering implementing the content of this blog, and always advise the seller to seek independent advice.
To learn more about the financial due diligence process in buying a business, why not purchase the book “Buying a Business The Smart Way” By Johann Goree: https://amzn.eu/d/0anwcVBk