Custom software can transform how a business operates. It can also become an expensive project that nobody uses. The difference is usually decided before a single line of code is written.
1. What problem costs you the most today?
Be specific. “We need an ERP” is a solution. “Our team spends two days every month reconciling sales across branches” is a problem, and it tells you exactly what the first release should fix.
2. Who will use it every day?
Software succeeds or fails with its daily users. Involve them early. If they don’t trust it, they will quietly go back to the spreadsheet.
3. What is the smallest version that helps?
The first release should be small enough to ship in weeks, not quarters. Real usage will teach you more than any requirements document.
4. Who will own it after launch?
Make sure you own the code, the accounts and the documentation. Ask how updates, security patches and hosting will be handled, and what it costs.
5. How will you know it worked?
Agree on a measure before the project starts: hours saved, errors reduced, orders processed. Without one, success becomes a matter of opinion.
A good technology partner will ask you these questions before you ask them. If a proposal arrives without them, that tells you something.