Passisto
Onboarding

Customer Onboarding Check-In

A customer onboarding check-in is a short conversation held in the first weeks after a customer signs up, to find out whether they are getting started smoothly. Most early churn starts with a customer who is stuck and says nothing. These questions help you catch blockers, confirm expectations and get the customer to their first result, and they work well as a spoken conversation.

17 questions

When to use this template

  • One to three weeks after signature or activation, while the customer is still setting things up.
  • When onboarding is taking longer than planned or the customer has gone quiet.
  • At the end of a defined onboarding phase, before handing over to the regular follow-up.

Questions to ask

Opening and first impressions

  1. 01Welcome on board. How have your first weeks with us been?
  2. 02What was your first impression when you started?
  3. 03What did you expect to achieve in these first weeks?

Getting started

  1. 04What have you been able to set up so far?
  2. 05Is there a step where you got stuck or lost time?
  3. 06Was the information we gave you clear enough to move forward alone?
  4. 07Who in your team is involved, and are they all on board?

Support and communication

  1. 08Have you had enough help from our team so far?
  2. 09How easy is it to reach someone when you have a question?
  3. 10Is there anything you would have liked us to explain earlier?

First value

  1. 11What is the first result you want to see from using us?
  2. 12Have you seen any sign yet that it is working for you?
  3. 13What is still missing for you to feel fully up and running?

Next steps

  1. 14What would be most useful for us to help with in the next two weeks?
  2. 15Is there anything that worries you as you go on?
  3. 16Is there anything you would like us to do differently?
  4. 17When would you like us to check in with you again?

Tips for a useful conversation

  • Link the conversation to the goal the customer gave when they signed, not to your own checklist.
  • Ask what has been done, not only how they feel: concrete progress is the best sign of a healthy start.
  • Listen for the silent blocker: a missing internal approval, a colleague who is not convinced, a lack of time.
  • Turn each blocker into a named action with a date and an owner.
  • Keep the tone warm; a new customer is still deciding whether they made the right choice.

Mistakes to avoid

  • Waiting until the customer complains before checking in.
  • Walking through your onboarding steps without asking what the customer actually needs.
  • Speaking only to the project sponsor while the real users are unheard.
  • Leaving the call without an agreed next step.

Let Passisto Clients hold these conversations

The AI agent calls your clients, asks the right follow-up questions and gives your team a clear report with the actions to take.

Customer Onboarding Check-In: Questions and Free Template | Passisto