Do not just start a trial. Decide what you are testing.

1. Criterion 01

   Problem fit

   What you are checking

   Whether the software addresses the failure you can name in one sentence, rather than a category you have been told you need.

   Ask the supplier

   Which specific step of my current process does this replace, and what happens to the steps either side of it?

2. Criterion 02

   The functions that matter

   What you are checking

   The three or four capabilities without which you would not buy, separated from the long list that makes a demonstration look impressive.

   Ask the supplier

   Which of my must-have functions are in the tier I am being quoted, and which sit one tier above?

3. Criterion 03

   Usability for the people who are not you

   What you are checking

   How the least enthusiastic member of the team gets a record in, on the device they actually carry.

   Ask the supplier

   What does it take to log a call or update a record from a phone, in taps?

4. Criterion 04

   Set-up effort

   What you are checking

   The hours between signing up and the first genuinely useful day, and who is going to spend them.

   Ask the supplier

   What is configured for me, what do I configure, and what needs a paid specialist?

5. Criterion 05

   Integrations

   What you are checking

   Whether it connects to the systems you already pay for, natively or through a connector you will also pay for.

   Ask the supplier

   Which integrations are native, which need a third-party connector, and what are the API rate limits?

6. Criterion 06

   Your data going in and out

   What you are checking

   Import quality and, more importantly, export completeness: records, history, attachments, custom fields.

   Ask the supplier

   Can I export everything myself, today, and does the export include activity history and files?

7. Criterion 07

   Access and security

   What you are checking

   Roles, permissions, audit trail and where processing happens, in proportion to the sensitivity of what you will store.

   Ask the supplier

   Can permissions be set per record and per field, and is there a log of exports and deletions?

8. Criterion 08

   The real cost structure

   What you are checking

   The model rather than the headline: per user, per account, metered, or a mix, plus what is billed on usage.

   Ask the supplier

   What is the total at the size I expect to be in eighteen months, including usage and add-ons?

9. Criterion 09

   Fit as requirements change

   What you are checking

   Whether the shape of the product still works when volume doubles or a second team joins.

   Ask the supplier

   What is the first limit I will hit, and is it a setting, a tier or a rebuild?

10. Criterion 10

    Help when it matters

    What you are checking

    What is included at your tier, in your time zone, and what the documentation looks like when you search it under pressure.

    Ask the supplier

    What response time is contractual at my tier, and what is charged separately?

11. Criterion 11

    Leaving

    What you are checking

    What cancelling looks like, what happens to the data afterwards, and what would have to be rebuilt elsewhere.

    Ask the supplier

    How do I cancel, how long is data retained after that, and what cannot be exported at all?

Nobody should apply all eleven to every purchase. A tool bought for one team for fifteen pounds a month deserves three of them; a system that will hold customer records for the next five years deserves all of them, in writing. The value of the list is that it is written before the sales call, when you are still calm.