Before Signing
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Separate what a document answers from what only use answers. Price at every tier, tier triggers, auto-renewal terms, export format and cost, the processing agreement, subprocessors, certifications and support terms are all facts somebody wrote down.
Usability, speed at your volume, real support quality and adoption are not, and no site assessing them from a desk is describing anything but marketing material. For a related operational perspective, Monitask also publishes a reference on ways employees can cheat time trackers.
The two halves fail differently. A usability problem is visible in a week and recoverable. A contract problem is invisible for a year and is not — which is why the checkable half deserves the attention it does not get.
A pricing page is a designed document, and the headline is rarely what you pay: check the billing unit, monthly against annual, minimums, what triggers the next tier, what is billed separately, renewal terms, and tax.
For broader context, see TrustRadius.
Organisation-essential features sit one tier above team-essential ones, so the real price is discovered after adoption at the point of least leverage. A free tier's limit is placed at the point of dependence rather than the point of value.
For broader context, see Salesforce.
And all of it compresses into twelve questions in one email, sent to every shortlisted vendor on the same day, before the trial rather than after.
The section also covers the processing agreement and the eight elements Article 28(3) requires; subprocessors, where the notice term matters more than the current list; certification badges, which state a scope, a period and an auditor that are none of them on the badge; auto-renewal windows, where missing a date costs a full term; and support terms, which are checkable where support quality is not.
Auto-Renewal
A date in a contract nobody diarised is the commonest way organisations pay for another year of a tool they had decided to leave.
The Processing Agreement
If the vendor touches personal data you need one, and Article 28(3) lists what it must contain. Eight items to check against.
What Free Omits
A free tier is designed to be adequate until you depend on it. Six things it usually withholds, and where the limit is placed.
The Next Tier Up
You will not stay on the tier you are buying. What sits one level above, and why that is the price you should compare.
Reading a Pricing Page
The headline figure is the least informative number on the page. Seven things to extract before comparing anything.
Security Claims
A badge on a website says a scope, a date and an auditor. Four things to check before treating it as assurance.
Subprocessors
Your vendor has vendors. Who they are, how they change, and why the notice term matters more than the current list.
Support as Written
Support quality cannot be checked before buying. Support terms can, and they are a different and more useful thing.
The Twenty-Minute Check
Twelve questions, one email, before anybody signs. The whole checking section compressed into something you will actually do.
What You Can Verify
Half of what decides a software purchase is checkable from documents. The other half needs installation and months. Which is which.