‘How was your day?’ is a useful opening, but it can become a routine exchange of ‘Fine.’ A more specific question sometimes gives the person an easier way into the story.
Try following something they mentioned earlier: ‘Did you get a chance to finish the drawing?’ or ‘How did the first session feel?’ The question shows continuity rather than requiring them to summarize an entire day.
Avoid turning remembered details into surveillance. Knowing about someone’s schedule does not mean they owe an account of every task. Leave room for a short answer or a change of subject.
You can also ask about experience rather than performance: ‘Was there a good moment in the day?’ That may invite a different conversation from checking whether a list of activities was completed.
Share something of your own when appropriate, so the exchange does not feel like an interview. A small observation can make the conversation easier to join.
Before choosing a question, consider whether the person seems ready to talk. Sometimes a greeting and a little space are better than a sequence of prompts. A good daily check-in helps two people meet in the present moment. It does not need to extract a detailed report to count as connection.