A wellbeing check-in is only as good as the question behind it. Ask “how are you?” and you get “fine”. Ask the right thing, in the right way, and you get an honest answer you can act on.

Here are twenty check-in questions that tend to start real conversations, grouped by what they reveal. Use them in a school, a team or a community program. The trick is not the list, it is how you ask, so there is a short section on that at the end.

Connection

How connected someone feels is one of the strongest signals of how they are really going.

  • How connected do you feel to the people around you this week?
  • Is there someone you could talk to if things got hard?
  • Have you felt like you belong here lately?
  • When did you last have a conversation that left you feeling better?

Confidence and mood

  • How are you feeling about the week ahead?
  • How confident are you feeling right now?
  • What is your energy like today?
  • How often have you felt calm and settled this week?

Workload and pressure

For teams especially, these map directly to the psychosocial hazards a workplace has to keep an eye on.

  • How manageable has your workload felt this week?
  • How much say do you feel you have over how you work?
  • Is anything getting in the way of doing your best work?
  • How well supported have you felt by the people around you?

Purpose and growth

  • Do you feel like what you are doing matters?
  • Are you learning or growing at the moment?
  • What is one thing you are proud of this week?
  • What would make next week better than this one?

The open door

Always leave room for the thing your set questions did not ask about.

  • Is there anything you want someone to know?
  • What is one thing on your mind right now?
  • If you could change one thing this week, what would it be?
  • How can we help?

How to ask so people actually open up

The questions do the work only if the way you ask them feels safe and low effort. A few things make the difference:

  • Use a scale, then one open line. Scoring how you feel from one to ten is quick and non-threatening. One optional comment box lets people say more if they want to.
  • Ask regularly. A single check-in is a snapshot. Asking each week or fortnight builds trust and shows a trend.
  • Be clear on who sees it. People answer honestly when they know whether it is private, anonymous, or shared with a specific person.
  • Do something with the answer. Nothing kills a check-in faster than asking and then never following up. The point of the question is the conversation it starts.

If you want a check-in that asks these kinds of questions and puts the results in front of the right person, take a look at how iyarn works for schools and workplaces, or start free today.