Choosing software
"We'll customise it later" usually means never
The gap between what a system does and how you work does not close on its own. It gets papered over with side registers, which become the real system.
Every implementation reaches a moment where something does not fit. A field that does not exist. An approval step your business needs and the software does not have. A report that is nearly right. The sensible-sounding response is to go live now and customise later.
Later rarely arrives, and the reason is not laziness.
What actually happens
The team finds a workaround on day three, because they have work to do. The workaround becomes habit by week two. By month three it is simply how things are done, and nobody raises it any more — not because it stopped hurting, but because it stopped being news.
Six months on, the request never gets made. The gap is still there, being paid for daily in small amounts of time nobody measures.
Which gaps matter
Not all of them. Most differences between how software works and how you work are worth adapting to, because the software's way is a reasonable way and yours was an accident of history. Genuinely wanting a field in a different order is not a requirement.
The gaps that matter are the ones where your business has a real constraint the software cannot express. A trade where goods are sold by weight but bought by carton. A practice where a matter cannot be billed until a specific approval exists. A workshop where the same part number means two different things depending on the supplier.
Those do not go away with familiarity. They generate a side register — a notebook, a spreadsheet, a WhatsApp group — and side registers are where your real data ends up living.
The question to ask before you go live
Not "can this be customised?" — everything can, given time and money. Ask: if this is never customised, what will we do instead?
If the answer is "we'll manage", go live. If the answer describes a parallel record someone will maintain by hand, fix it before launch, or accept that you are buying a system plus a shadow system.
Why we ask about this early
We would rather find the real constraint in the first conversation than at go-live, because at go-live it becomes a crisis with an audience. It is also the fastest way to find out that a business does not need custom work at all, which is a good outcome and a common one.