Follow up an expiring trial

A trial ending is the only moment you are guaranteed their attention, and a generic reminder wastes it. The whole value of this procedure is in step two.

Steps

1. List the trials ending in the next few days, with their start date, the account, and who signed up.
2. Read what each one did. Group them, because the right message is different for each and sending the wrong one is worse than sending nothing:
   • Never activated: signed up, did nothing. The message asks what got in the way, and offers to extend. It does not sell.
   • Started and stopped: set something up, then nothing for a week. Something specific blocked them, and finding out what is worth more than the renewal.
   • Using it properly: regular activity, several people, real volume. This one is a conversation with a human being, today, and it goes to whoever owns the account.
   • Using it in a way the plan will not hold: already past what the paid tier allows. That is a pricing conversation, not a reminder.
3. Check the CRM before writing anything, for an owner, an open opportunity, or a previous conversation. A reminder that ignores a live conversation is embarrassing in a way customers remember.
4. Draft one message per group, naming what they did — "you connected three tools and ran 200 calls last week" beats any adjective — and what happens on the end date, exactly.
5. Hand the fourth group and anything with an owner to a person, with a two-line brief of what they did and what to ask.
6. Record the outcome on each account so the next cycle starts from what happened.

Stop and ask

• Before extending a trial, discounting, or promising anything about price.
• Before emailing anyone at an account with an open opportunity — their owner sends it.