When you really want to know how someone is doing, what’s the best way to ask?
A meaningful and effective check-in goes beyond “how are ya?” In fact, it’s kind of an art form. There are so many ways to do it, and it depends on the relationship. Here are some practical suggestions to try out:
Checking in on a friend:
- What’s something that’s true of you today?
- What’s taking up your headspace lately?
- What’s getting most of your time and energy these days?
Checking in on someone you lead:
- What’s something you feel confident or energized about right now?
- What’s something you’re unsure of, concerned about, or unmotivated to do right now?
- What can I do to support you?
Checking in on a child after school:
- How did you show kindness today?
- When did you feel most proud of yourself today?
- Who brought the yummiest lunch today?
Checking in on a partner:
- What’s something I did this week that made you feel loved?
- What’s something that’s weighing heavily on you right now?
- What’s capturing your imagination lately?
Whomever you’re checking in with, here is my top suggestion:
Be specific!

One Simple Shift. Three Powerful Messages
For example, beforehand, think back to some challenging thing they faced recently. Maybe it was a snag in a project or goal, a difficult interaction with a friend or client, or an illness that lasted way too long.
Whatever it was, check in with them on that pain point.
Just a simple change from “how are you” to something much more specific communicates three things. First, you noticed they went through something hard. Second, you kept them in mind. And third, you cared enough to follow up.
A specific check-in takes time, thoughtfulness, empathic attention, and genuine care. Those are key ingredients to compassionate communication. And in terms of laying groundwork for a genuine connection, they simply can’t be beat.
Warmly,
Andrea Hollingsworth