We are a software house, so take this in the spirit it is written: these are the questions that would make our own sales conversations harder, and every one of them is worth asking. Including to us.
Most bad software projects in Pakistan do not fail because the developer could not code. They fail because nobody asked the awkward question in month zero.
1. “Who actually writes the code, and will I meet them?”
In a small software house the person selling is often the person building. That is good — nothing is lost in translation. In a larger one, the salesperson may never speak to the developer again after signing.
Good sign: you meet the developer during the sales process.
Warning sign: “our technical team will handle that” and you never see them.
2. “Show me this working with data like mine”
Every demo looks good on the vendor’s prepared data. Ask them to show your scenario — your item types, your process, your awkward case. If you dye fabric in lots, ask to see lot tracking. If you sell in cartons and pieces, ask to see both units on one invoice.
Warning sign: “we can build that” for something they claim is a standard feature.
3. “What happens when I need a report you did not build?”
This single question tells you what the next three years cost. Every business needs reports nobody thought of at the start.
Good sign: a per-report rate, or a report builder you can use yourself.
Warning sign: every new report is quoted as a fresh project with a fresh timeline.
4. “Where will my data live, and can I have it?”
You should be able to get a full copy of your own database, in a standard format, whenever you want — without asking permission and without a fee.
Warning sign: any hesitation. If leaving is difficult by design, that is not a technical constraint, it is a commercial strategy.
5. “What is in the quotation, and what is definitely not?”
Ask for the exclusions list in writing. Data migration, training, server setup, report changes and post-warranty support are the five things most often assumed by the buyer and excluded by the vendor.
The exclusions list prevents more arguments than the inclusions list. If a vendor will not write one, they are relying on the ambiguity.
6. “How is it billed, and against what?”
Payment should track delivery. A large advance with the rest “on completion” leaves you exposed, because completion is exactly what becomes disputed.
Good sign: staged payments, each tied to a module you can actually use.
Warning sign: most of the money before anything works.
7. “What happens to my old data?”
Opening balances, party ledgers, item history, stock. Ask specifically: what is migrated, what is not, and who reconciles the totals. This is the most under-quoted line in the industry, and the one most likely to blow the timeline.
8. “Can I speak to a client you delivered to two years ago?”
Note the two years. Recent clients are still in the honeymoon. The interesting question is what a relationship looks like after the warranty ended, the original developer moved on, and the business changed.
Warning sign: only very recent references, or none at all.
9. “What happens if you are not available?”
Ask it directly. A one-person shop is not disqualifying — plenty of excellent systems come from one person — but you should know, and there should be an answer: documented code, a second developer who knows it, a copy of the source with you.
10. “What would you tell me not to buy?”
Our favourite question, because the answer is hard to fake. A vendor who understands your business will name something in their own proposal that you do not need yet.
Warning sign: “you need all of it.” Nobody needs all of it in month one.
Two more things, on the quiet
Watch how they handle the awkward question. You are not really testing the answer. You are testing whether they get defensive — because that is exactly how they will behave when something breaks in month eight.
Beware the vendor who agrees with everything. If you describe your process and nobody pushes back on anything, they either were not listening or intend to build exactly what you said and let you discover the problems later. A good vendor argues with you at least once during scoping.
Ask us all ten. We would rather answer them now than have you find out in month eight. Get in touch, or see our published pricing and quote builder — both of which exist so you can judge us before you ever call.