The question is time to first value
If someone can sign up and get something genuinely useful within about fifteen minutes, a free trial works. If reaching value requires importing data, connecting systems or getting three colleagues involved, an unaccompanied trial mostly produces abandoned accounts.
That is the whole decision. Everything else is implementation.
Where trials fail
- Empty product, no sample data, no obvious first action
- Setup requiring information the trialist does not have to hand
- A trial period shorter than the time it takes to get internal buy-in
- Nobody contacting the trialist until day 13 of a 14-day trial
- Restricting exactly the feature that would demonstrate the value
The most common trial mistake is hiding the killer feature behind the paywall. The trial exists to show why the product is worth paying for; withholding that is self-defeating.
Where demos fail
A demo that is a feature tour rather than a conversation about the prospect's problem. A demo booked three weeks out, by which time the interest has cooled. A demo with no next step attached.
Demos also fail when they are the only route in: buyers increasingly want to try before they talk, and forcing a call loses the ones who will not.
The hybrid that usually works
- Short qualifying call or form to understand the situation
- A demo focused on their problem, not on your feature list
- A trial with their data loaded and the setup done for them
- A check-in at day two or three, when problems are still fixable
- A decision conversation before the trial ends rather than after
Instrument the trial
Track whether trialists reach first value and how long it takes. That single measure predicts conversion better than any other, and it tells you what to fix.
Contact those who have not reached it, by day two, with something specific rather than a generic check-in email.
Trial length
Fourteen days is conventional and often wrong. Match it to your buying cycle: if the decision needs a manager who is away for a fortnight, a 14-day trial expires before the decision is possible.
Extending on request is nearly always the right answer. A trialist asking for more time is engaged, which is the opposite of a reason to refuse.