Software · checklist
Nine Questions to Ask Before You Buy Any Business Software
The questions that expose the real cost of a subscription: users, tiers, data export and what happens when you leave.
Software is sold on the headline price of the tier you will outgrow. These nine questions, asked before you enter a card number, surface almost every cost that appears later.
Cost and contract
- What does this cost per month with the number of users I will have in a year, not today?
- Which of the features I just watched in the demo are on a higher tier?
- Is the advertised price annual-billing only, and what is the monthly equivalent?
- What are the transaction, payroll or per-invoice fees on top of the subscription?
Data and exit
- Can I export my customers, invoices and history in a usable format, on my own, without support's help?
- If I stop paying, do I keep read access to historic records, and for how long?
- Who owns the data, and where is it stored?
Work, not features
- Which task in my week gets shorter because of this, and by how much?
- What will I stop paying for once this is in place?
Run a two-week real trial
Use the trial on live work, not sample data. Enter last month's real jobs. Software that cannot handle your awkward cases in a fortnight will not handle them in a year.
A reasonable software budget
| Business size | Typical monthly software spend | Usually covers |
|---|---|---|
| Sole trader | £20–£60 | Accounting, storage, one scheduling or quoting tool |
| 2–5 people | £80–£250 | The above plus shared email, CRM, payroll |
| 6–15 people | £300–£900 | Adds project management, HR, phone system, security |
If your spend is well above the band for your size, the cause is nearly always duplication: two tools doing one job because nobody cancelled the first.
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