Dr. Andrea Hollingsworth
Hollingsworth Consulting

When you really want to know how someone is doing, what’s the best way to ask?

In a recent podcast interview, I mention how meaningless and ineffective the question “how are you” has become. It’s basically like saying “hi.” Almost no one feels like it’s a genuine invitation to really connect.

A meaningful and effective check-in is 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 a direct report:

  • 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?
  • How can I support you?

Checking in on a child after school:

  • How did you show kindness today?
  • When did you feel most proud of yourself today?
  • What was the hardest part of 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!

Before you talk to them, think back to some challenging thing they faced recently. Maybe it was a snag in a project, a difficult interaction with a friend or client, or an illness that lasted way too long.

Then, whatever it was, check in with them on that pain point. 

For instance: “Hey, I know that person/assignment/customer/friend/project really sapped your energy last week. How are you holding up? Have you had a chance to catch your breath?”

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.

And hey. If you swap a simple “how are you” for one of these check-in suggestions this week, drop me a note! Let me know how it went. I’d love to hear from you.

About Andrea

Dr. Andrea Hollingsworth is Founder and CEO of Hollingsworth Consulting, author of the bestselling book The Compassion Advantage (2024), and one of today’s leading global experts on compassionate leadership. Since 2008, she has been studying, speaking, and writing about the science and spirituality of human emotions and relationships. Her articles have been published more than a dozen times in peer-reviewed journals, and she has taught at prestigious institutions like Princeton, Boston University, and Loyola University Chicago. In addition, Dr. Andrea has delivered talks to audiences at some of the top-ranked universities in the world—including Cambridge University in England and Heidelberg University in Germany.

Dr. Andrea spends most of her time inspiring leaders and teams to use The Compassion Advantage to build supercharged organizations through cultures of care— especially in times of challenge and change. Andrea lives with her family in Minnesota where she cheers hard at her son’s soccer games and relishes every opportunity to visit the north shore of Lake Superior.