How to Have Effective Check-in Conversations

How to Have Effective Check-in Conversations 1080 608 Jason Lauritsen

It was my birthday and I was craving some time with my kids.

In a brazen attempt to pry my kids away from their technology, I offered a trip to Dairy Queen for some ice cream. My hope was, once they were a captive audience in the car, we’d be able to chat a bit.

But before we could even get loaded into the car, a shouting match exploded between the two of them. Apparently, my son (the thirteen-year-old) “slammed” the door before my daughter (the fifteen-year-old) could walk through it. She was startled and took immediate offense to this crime of epic proportions.

In a flash, there was screaming and accusations flying back and forth, with my dream of a fun ice cream outing quickly fading.

Eventually, I got the two of them calmed down enough to get in the car. They weren’t happy with each other, but their love of ice cream ultimately prevailed.

As we drove, I asked each of them some questions just to get them talking. We chatted about school and friends. The heat of the fight slowly faded as we drove.

Then, as we were waiting in the drive-thru lane for our ice cream, something surprising happened.

My son, from the backseat, said this, “Bailey, can we talk about what you think is funny?”

This struck me as a strange question, but Bailey was curious enough to say “Sure.”

He wanted to talk about what had happened back at the house. He shared that he thought closing the door right in front of her was funny, but now realized she didn’t think it was funny at all.

In the next few minutes, they talked about how slamming doors is never funny because someone can get hurt. He asked a few thoughtful questions, listened to what she said, and then said, “Okay, I won’t do that anymore.”

And just like that, the wound of the fight was healed.

Having the Conversations that Matter

This entire exchange took place in the span of just a few minutes.

My son asked a question that felt really important to their relationship. That question, in turn, created a meaningful conversation. He listened, reflected, and then decided to do something to make the relationship better.

Let me be clear, I’m not sharing this story as some evidence of my parenting skills. I was floored by the whole interaction.

They are good kids and they are thoughtful kids, but they can be pretty vicious to one another as siblings tend to be. This was not typical behavior.

The reason I share this story is that my son, in this moment, did exactly what I teach people to do with check-in conversations. I wish I could take credit for teaching him the steps. But if he learned it from me, it’s been simply through observation.

He used a check-in conversation to quickly repair some damage to a relationship that mattered to him.

It was such a simple and beautiful example of the incredible power of bravely stepping into a meaningful conversation with someone who matters to you.

The check-in conversation, as I teach it, is a technique to skillfully invite the conversations that matter with all of the important people in your life. It’s a vital skill to master as a manager and leader, but it’s also vital if you want to be a great partner, parent, or friend.

Pushing through the discomfort

Learning to have effective check-in conversations is simple. Every effective check-in conversation involves four steps which I will share with you below.

Knowing how to check-in is actually the easy part. The more challenging step is finding the courage to have these conversations instead of avoiding them. They often lead us to places that many find uncomfortable. When you skillfully check-in, you frequently hear things you may not like or aren’t prepared for.

In my son’s case, he learned that he was mostly at fault for what had happened. And, if he wanted to avoid this experience in the future, it was on him to make a change. I’m proud of how he responded because it required courage and vulnerability.

When you check-in well, you can get to the truth of what’s really going on with the other person. Whether hearing it makes you uncomfortable or not is irrelevant because it is their truth and their reality.

Learning to embrace the discomfort of hearing these realities is important because knowing is always better than not knowing if you want to foster strong relationships.

Four Steps of an Effective Check-In Conversation

Every check-in conversation, regardless of whether it’s with your direct report or your sister, has four steps.

Whether you want to generally check-in on someone’s well-being, the status of your relationship, or career progression; this four step process will ensure that you have a meaningful conversation regardless of the topic.

Check-In Conversation Step #1: Ask a great question.

Most well-intentioned check-ins go wrong before they even get started because we ask bad questions.

We are all guilty of it. Think about the last time you checked-in with someone. What question did you ask them? I’d bet it was one of the following:

  • How are you?
  • How’s it going?
  • How have you been?

All seemingly nice questions, but what kind of response do you typically get to these questions?




One word that tells you nothing other than they don’t really believe you want to have a conversation with them.

Asking a great question is the key to a great check-in. A great question is one that invites a response that requires a follow-up.

My son’s question in the car was a great example. When he asked “Can we talk about what you think is funny?” whatever she responded with was going to require some follow-up conversation. It would have been impossible to leave it there.

My favorite, universal check-in question is actually a simple modification on one of the questions above. Here it is.

How are you on a scale from 1 to 10 with 10 being “couldn’t be better” and 1 being “couldn’t be worse”?

The beauty of this question is that it doesn’t take long for them to respond and whatever number they share is a doorway into a meaningful conversation.

Any question that invites a response that requires a follow-up is likely a great question for a check-in conversation. You can click here to download my list of 18 Great Check-In Questions.

This brings us to the obvious next step.

Check-In Conversation Step #2: Ask the follow-up question(s).

Once you ask a great question and get the initial response, you obviously need to ask the follow-up question or questions that foster the conversation that matters.

The important thing to remember when asking the follow-up question(s) is that the goal of the check-in is for you to get an understanding of what’s really going on with the other person. This means being open, curious, and non-judgmental – regardless of what they say. (This is where embracing discomfort is important).

The follow-up questions you ask will depend on what great question you started with.

For the question I shared above, the follow-up depends on the number the person shares with you.

  • If they share a higher number like a 9, it’s an invitation for you to learn about and connect with them. You might ask, “What’s going well for you right now?”
  • If they share a lower number like a 2 or 3, your follow-up will be different. “That’s not good. What’s pulling that number down for you today?”

The follow-up question opens the door to the conversation you want to have. Be thoughtful, curious, and caring in your follow-up and the person on the other side of the conversation will usually reward you by sharing.

Check-In Conversation Step #3: Shut up and listen.

While this may seem obvious, the next vital step is to close your mouth, open your ears (and eyes) and really listen to what’s being shared.

When we ask a great question and a thoughtful follow-up, the sharing and conversation that really matters can begin. To get the most out of this opportunity, it’s critical to pay close attention to what’s being communicated. This includes what’s being said, but also what’s not being said along with the non-verbals being shared as well.

Listen patiently and allow the person to open up. When it makes sense, ask more follow-up questions.

Your goal is to learn and understand what’s really going on with that person. And once you’ve done that, you can move to the final step.

Check-In Conversation Step #4: Offer support and encouragement.

The last step of an effective check-in is to connect the conversation to your desire to be supportive of the other person.

If the conversation reveals that the individual is struggling, what support can you offer to them to help them through the challenges? This doesn’t mean you have to solve their problem. In fact, it’s often more powerful to ask a question like “How can I help?” or “What does support from me look like for you right now?”

If the conversation focused more on what’s going well, then closing the conversation with some appreciation and gratitude for the individual could be warranted. Or you might share how excited you are for them and ask if there’s anything you could do for them to be supportive.

In the example I shared with my kids, the check-in conversation was to repair a rift in the relationship and revealed an opportunity to do something different in the future. So, my son closed out the check-in by committing to behaving differently in the future.

More Check-In Conversations = Better Relationships

Being a great manager has everything to do with the relationships you build with your people. To foster a loyal, high-performing team requires that you invest in building relationships with each individual.

Strong relationships require strong communication. Mastering the check-in conversation is the key to building better relationships with your people. And as a bonus, it will help you improve every other relationship in your life as well.

I recently posted a video on my YouTube Channel outlining how to check-in effectively. You can visit that video by clicking on the video below.


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Jason Lauritsen