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Check-in questions that get an honest answer

"How's it going?" gets "fine". These don't. For a weekly coffee, a Sunday text, or the evening reflection.

By the LeadMeNot team · Updated November 7, 2026 · 4 min read

The short version

  • Ask about the day, not the sin. Tired, lonely, bored and angry predict slips better than anything.
  • Ask what they want to tighten, not what they did wrong. It keeps them in charge of their own plan.
  • Two minutes daily beats an hour monthly.

The weekly five

Pick a regular time. Ask these, in this order, and then stop talking.

  1. What was the hardest moment this week, and what was going on that day?
  2. Was there anything you nearly did, and what stopped you? (This is the question that reveals what's working.)
  3. Did anything get through? (Ask it plainly. They'll know you can handle the answer because you asked it plainly.)
  4. Is there a rule you want to tighten, or one that's too tight to be realistic?
  5. What do you need from me this week?

The two-minute daily version

If they send a LeadMeNot evening reflection, you already have this. If not, one text:

"Day out of 10, and one word for why?"

A "4, lonely" tells you more than a paragraph. Reply to it. Even "noted, here if you want to talk" counts.

For gambling specifically

  • "Did you look at odds, lines or a betting site this week, even without betting?"
  • "Any money moved that you'd rather not explain?"
  • "Is the bank block still on, and is self-exclusion still in place?"

Questions to skip

  • "How many times?" Counting turns it into a scoreboard and the scoreboard becomes the shame.
  • "Why do you keep doing this?" They don't know. If they did, they'd have stopped.
  • "Do you still find me attractive?" Fair to feel. Better asked with a counselor than at check-in.

Make it routine, not a trial

Same time each week. Same questions. Short. The predictability is the point: they know what's coming, so they can tell the truth without being ambushed. If you're using LeadMeNot, the partner guides cover what the alerts and reflections mean, so the check-in can be about the person rather than the data.

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Questions

How often should accountability partners check in?

A two-minute daily touch (a score out of ten and one word) plus a short weekly conversation works better than a long monthly one.

What should I ask my accountability partner each week?

The hardest moment and what was going on that day; what they nearly did and what stopped them; whether anything got through; what to tighten or loosen; and what they need from you.