What to ask a software supplier before signing

A demonstration is built to be watched. The questions below are built to be answered, and most of them are harder to answer than to ask. Half an hour spent on them before signing tends to teach an agent more than a month of trialling afterwards.

What does it do on a difficult day

Demonstration data is tidy. Block management is not. The service charge year that closed three weeks late, the flat that changed hands mid-quarter, the contractor invoice that arrived without a purchase order and the leaseholder who writes in every fortnight are the conditions the software actually has to survive.

So the request is a simple one: show it handling the mess. Better still, send a redacted sample of real correspondence or a genuine budget in advance and ask the supplier to run it live on the call. Suppliers who are confident will do it. Suppliers who steer back towards a case study have answered the question anyway.

Whose data is it, and what leaves with it

Software is easy to enter and hard to leave. The moment worth planning for is the one nobody raises during a sale: the day the agent moves to something else.

Two answers matter. The first is what an export actually contains. A list of unit references and balances is not the same thing as the correspondence history, the document store, the job records and the trail of who approved what and when. The second is the format it arrives in. A file only the supplier's own system can open is technically an export and practically a lock.

This is not an abstract worry in this sector. Section 20B of the Landlord and Tenant Act 1985 makes costs incurred more than 18 months before a demand is served unrecoverable, unless the leaseholder was notified in writing inside that window that the costs had been incurred and would be charged. Proving that notification happened means producing a record, possibly years later, and possibly out of a system the agent stopped paying for in the meantime.

What does it connect to, and who does the connecting

Most agents run more than one system. The accounts sit in one place, the documents in another, and the property management platform in a third. Asked whether it integrates, a supplier will almost always say yes. The useful follow-up is who builds that integration, how long it takes, and what it costs.

"Available through our API" often means available to somebody the agent will have to go out and hire. That can be a perfectly fair answer. It simply belongs in the price rather than in the small print.

Where does the automation stop

This question has sharpened as suppliers add artificial intelligence (AI) features to established products. Drafting a status update, sorting an inbox and reading back through a year of correspondence are jobs a machine genuinely does well, and there are real hours in all three.

Statutory correspondence is a different animal. Consultation under section 20, a service charge demand, and the summary of rights and obligations required by section 21B are not drafting exercises. They are deadline and evidence steps, and when one goes wrong the consequence lands on the agent and the resident management company (RMC), not on the software.

The question, then, is not whether the system can generate a notice. It is what the system does to prevent one leaving unreviewed, and what the contract says about responsibility when one does. Most suppliers have thought carefully about the first. Noticeably fewer have written anything down about the second.

Who else uses it, and can we speak to somebody who left

Every supplier keeps a reference customer. The more revealing request is for a customer who has taken on blocks since going live, because growth is what exposes a system, and for one who has since moved away.

A supplier who can produce the second of those, and describe why the customer went, is a supplier who has been paying attention. Refusal is not proof of anything. It is still worth noting who offers and who does not.

What does this cost in two years

Pricing here is rarely one number. It moves with the number of units, the number of users, the volume of documents stored, or some combination of the three. An agent who takes on three more blocks does not want to meet the next pricing tier at the same moment.

Three things are worth establishing before signing: what triggers an increase, what existing customers have actually seen at renewal over the past two years, and whether the opening rate is a discount with an expiry date. The last of those has a definite answer, and it is usually yes.

Who does the work in week one

Implementation is where sound software quietly fails. Data has to be cleaned before it can move. Templates have to be rebuilt. Somebody has to be trained, and that somebody already has a full week.

The question is not whether onboarding is included, because it always is. It is how many hours of the agent's own staff time the supplier expects to consume, and in which weeks. A supplier who has done this many times can answer that precisely. One who cannot has just disclosed something useful.

The question underneath all the others

Software is bought to solve a problem, and in most purchases the problem is described by the demonstration rather than by the agent. That order is worth reversing.

Before any of the above, it is worth mapping where a fortnight actually went: what was done, by whom, and how many times. It is a dull exercise, it costs a couple of afternoons, and it converts a vague sense that the team is stretched into a specific list. A specific list can be tested against a specific product. A vague sense cannot, and it will be met, every time, with the same agenda: here is what this does well.

David Bevan is the founder of HoursBack.