Trial users signed up but never started. What should you send?

Send help with the next unfinished task. A person who has not created anything needs a different message from someone who saved a draft and got stuck sending it.

Before writing, check that your activity data supports the distinction. If you cannot see what someone did, ask them. Do not present a guess as something you observed.

This guide uses a fictional invoicing app. The people, events, and messages are illustrative, not customer results.

Choose one useful activation event

For this example, the first useful outcome is sending an invoice. Signing in, visiting the pricing page, and opening three emails do not prove that outcome happened.

Write down the event you want to help the user reach, how you know it happened, and the help available at each step. You do not need a complicated score to send a relevant question.

What you can verify	Likely next task	A question worth asking
Account created, no client added	Work out whether they have an invoice to send	“Is there an invoice you're hoping to send this week?”
Client added, invoice saved as a draft	Resolve a question before sending	“Is there anything you need to check before sending your first invoice?”
First invoice sent	Find out whether the result met their needs	“Did that invoice do what you needed, or is anything still missing?”

These are possible next steps, not claims about the user's intentions. Give them room to correct you.

When they signed up but created nothing

Subject: Your first invoice

Hi Ava,

Is there an invoice you're hoping to send this week? If you tell me what you need to bill for, I can point you to the right setup steps.

Sam

Use a message like this when someone has a reason to hear from you about their trial. It asks about their job rather than scolding them for not using your software. They may be comparing tools for next month, or have signed up for a colleague. Both answers are more useful than another login reminder.

Do not ask them to send a client's payment details or other sensitive information by email. Link to the appropriate account page if information must be entered.

When a draft is waiting

Subject: A question about your invoice draft

Hi Ava,

Is there anything you need to check before sending your first invoice? If you're working out deposits or payment terms, reply with the question and I can help.

Sam

Only mention deposits if the app supports them and you have a reliable guide. If Ava replies, “Can I take half now and half later?”, answer that question with verified steps. Do not turn the reply into a general product tour.

After sending the explanation, a later check-in can ask whether she managed to complete the task. If she has already sent the invoice, acknowledge that instead. A scheduled message based on old activity can undo the care in your first email.

When they completed the task

Hi Ava,

Did the first invoice work the way you needed? If you're deciding whether to keep using the app, is there anything you still need to check?

Sam

This is the point to answer a plan question if they have one. A successful first action does not automatically mean they need the most expensive tier.

If the product did not fit, ask whether they are willing to explain why. The feedback guide shows how to record those answers without turning a small sample into a sweeping conclusion.

Set stopping and handoff rules before sending

Stop the planned sequence when someone replies, declines, opts out, becomes a paying customer, or completes the step that made the message relevant. Resume only with a next action appropriate to the new situation.

If they ask for help outside the available guide, hand the question to someone who can answer. Do not invent billing terms, refund promises, or features. If they have a support issue, resolve or route it before asking for an upgrade.

For a non-responder, decide in advance whether one reminder is appropriate. The number and timing should reflect the relationship and trial length. There is no evidence in this guide for a universal “best” schedule.

Judge whether the help was useful

Record the starting state, message, reply, and whether the user completed the task. Include the people who did not answer. A handful of grateful replies can tell you what to improve, but cannot establish that your email caused an increase in paid conversion.

For a first pass, read the replies and look for repeated obstacles. If several people cannot work out deposits, fix the relevant product step or guide as well as the email.

The trial conversion use case outlines the information to prepare before giving OutreachGuy this job.