Price, at your real size, with everything on
The headline 'from' price is rarely what you'll pay. Ask for the total monthly cost at your actual headcount, on the tier that contains the two or three features you came for. Then ask the killer follow-up: 'What on that screen is an extra?' Add-ons, per-user fees, SMS bundles and payment-processing cuts stack quietly. Get the all-in number in writing, not the brochure number.
Contract, notice and exit
Is it rolling monthly or a fixed term? Commusoft, for example, asks for a 12-month contract that renews annually. What's the notice period, and does the price you're quoted today hold at renewal or step up? An honest vendor answers these without flinching. If the salesperson gets vague about how you'd leave, treat that as information.
Your data: ownership and export
Your customer list and job history are your business. Ask directly: 'If I leave in two years, exactly how do I get my customers, jobs and invoices out, and in what format?' A clean answer (a full CSV or similar export you can trigger yourself) is a good sign. 'Contact support and we'll help' is a softer one. Confirm you own your data outright, not just licence it back.
UK tax and your accounting package
Make the demo do your tax, not a generic invoice. If you're VAT-registered, ask them to show a VAT return or the VAT handoff to your accounting package. On CIS, ask them to run a deduction. Then confirm the integration with your specific package (Xero, Sage or QuickBooks) is on the tier you're being quoted, not a pricier one. This is the check UK buyers skip most and regret most.
Implementation, support and who actually uses it
Ask what onboarding involves, whether setup and training are included or extra, and how long a business your size typically takes to go live. For support, ask the channel and the realistic response time, then test it during your trial rather than taking the answer on faith. And ask for a reference customer in your trade and roughly your size; a confident vendor can point to one, and a similar business's experience is worth more than any feature grid.
Questions people actually ask
Should I get a demo or just start a free trial?
If the tool has a self-serve trial, start there. An evening running your own job on real data tells you more than any guided demo, because nobody's steering you past the rough edges. Save demos for products that are demo-led (like Commusoft) or for enterprise plans with no public price, where the demo is the only way to get real terms. Even then, book the trial afterwards if one exists.
Where to go next
Evidence & sources
Demo-led/contract terms context (Commusoft 12-month contract, quote-led, no public price list)
Commusoft (vendor), plans page · checked · vendor/commercial source
Prices and terms change. If a source above no longer matches what we've written, tell us via the corrections page and we'll fix it.