1. What is the total cost over the full term?
A headline monthly price tells you very little. Add up setup or onboarding fees, data migration, training, per-user costs as you grow, and anything billed as an 'optional' module you actually need. Compare suppliers on the total cost over three years, not the first month.
2. How long is the contract and what is the notice period?
Twelve-month terms with a ninety-day notice period are common, which means you effectively decide whether to stay after nine months. Diarise the notice date the day you sign. Auto-renewal clauses are where most businesses get trapped for another year.
3. Can the price go up mid-term?
Look for indexation clauses such as CPI plus a percentage. They are not unreasonable, but you should know the ceiling. Ask for a cap in writing if the contract does not include one.
4. What exactly does support include?
Get the response times, the hours of cover and the escalation path in writing. 'Business hours support' means something different to a supplier operating in another time zone. Ask what happens at 4pm on a Friday when your system is down.
5. Who owns the data?
You should own your data, be able to export it in a usable format at any time, and know how long it is retained after you leave. If the supplier processes personal data on your behalf, you also need a data processing agreement to satisfy UK GDPR.
6. What does leaving look like?
Ask the exit question before you join: how is data exported, is there an offboarding fee, and how long does the handover take? Suppliers who answer this comfortably are usually the ones worth signing with.
7. Can I speak to two customers like me?
Not a case study — an actual phone call with a business of similar size in a similar sector. Ask them what surprised them after signing. That single conversation is worth more than any sales deck.
A simple rule
If a supplier will not put an answer in writing, treat it as though the answer is no. Good suppliers expect these questions and respect you for asking them.