When a company starts looking for a document management system, the first comparison is usually a table of storage space, price per user and supported file formats. Those numbers are easy to compare, which is exactly why they are the wrong place to start. A document system does not fail because it ran out of gigabytes. It fails because people keep working around it.
Here are the seven questions worth asking before you sign anything.
1. Where will a document live in relation to your business data?
A document almost always belongs to something: an invoice, an employee, a project, a customer. If the system keeps documents in one place and your business data in another, somebody has to maintain the connection by hand — usually by naming files carefully. That discipline holds for a few months. Ask to see what happens when you open a supplier invoice: does its scan sit right there, or do you have to go looking for it?
2. Who decides who sees what?
In a shared folder, access rights are set by whoever created the folder, and nobody remembers why. Ask how rights are structured: per folder, per role, per department? What happens when somebody changes jobs internally? A system that cannot answer this quickly will end up with one folder that everybody can see, which defeats the point.
3. What happens to an incoming supplier invoice?
This is the single best test of a document system, because it is the most frequent document in most companies. Follow it end to end: it arrives by e-mail, and then what? Somebody downloads it, renames it, files it and retypes the amounts into accounting? Or does it land in an inbox where the data is read from the scan and the accounting entry is prepared for someone to confirm? The difference is measured in hours per week.
4. Are signing and approvals inside the system or beside it?
Approvals and signatures are where documents usually leak out of the system and back into e-mail. Ask whether a document can be sent for approval and for an electronic signature without leaving the system, and — just as important — whether the signed copy and the approval history come back and stay attached to the document.
5. How do you share a document with someone outside the company?
If the answer is an e-mail attachment, you have just made a copy that nobody controls any more. Look for the ability to share a folder or a document with a customer or partner as a link, with the original staying where it is.
6. How will you meet retention deadlines?
Business documentation has prescribed retention periods, and they differ by document type. In practice this only works if the retention date is a property of the document rather than something an accountant keeps in their head. We went through the Slovenian deadlines in a separate article: how long do we have to keep business documentation?
7. What happens when you want to connect it to something else?
A document system is rarely the last thing a company introduces. Ask what it takes to connect it to your ERP, to payroll, to a project tool. If every connection is a separate integration project, the cost of the system is not the licence — it is everything that comes after.
The uncomfortable conclusion
Most of these questions are not really about the document system. They are about whether the documents sit inside the system where the work happens, or in a well-organised archive beside it. An archive beside your business is still an archive: better than a filing cabinet, but it will not remove a single step of retyping.
If you want to see what this looks like when documents live in the same system as invoices, employees and projects, we described it here: a document system connected to your business.
How to choose a document management system: seven questions before you decide