Are You Okay? Try Asking a Better Question to Build Deeper Connections

“Are you okay?” It’s one of the most common questions we ask people, but it’s also one of the least useful.

You’re probably going to get an answer like “fine” or “good.” It’s a closed-ended question, and how you ask a question makes a huge difference in the type of information you get and what people are willing to share.

A closed-ended question can be answered with one word. Think about questions like: Are you okay? Did that upset you? Do you want to talk about it?

Now, these aren’t bad questions. They come from a good place, but they give the other person an easy exit. “I’m fine.” “Not really.” “It’s okay.” And they don’t necessarily deepen the conversation. That’s the shift we want to make.

An open-ended question can’t be answered with just one word. It encourages the other person to pause, think, reflect on a memory, and give you more detail. Try asking:

  • What was that like for you?
  • What’s sticking with you about that experience?
  • What do you need right now?

Notice that these questions start with “what.” It’s a little trick I use in my practice. I try to avoid “why” questions because they can carry a little judgment and tend to trigger people’s defensiveness. Instead of asking why, I look for more details and get into the what, where, and when. I’m trying to understand and be curious about someone’s experience. That way, I get more than just a single-word answer like “I’m fine.”

Here’s a simple one-word test you can use mid-conversation. Think about the question you’re about to ask. Can it be answered with “yes,” “no,” or “fine”? If so, consider whether you can ask it in a more open-ended way.

For example:

  • Instead of “Are you stressed about work?” try “What’s been the hardest part about work lately?”
  • Instead of “Do you need some help?” try “What would be most helpful right now?”
  • Instead of “Is everything okay with you two?” try “How are things feeling for you two right now?”

It’s the same concern and the same care behind the question, but it’s structured so people can open up more and be more honest and thorough with their answers.

When Closed-Ended Questions Are the Better Choice

Here’s a quick caveat: open-ended questions aren’t always the right move. There are situations when you’ll want to use closed-ended questions.

If somebody is shut down, overwhelmed, or in an acute crisis, this is a time when you want to be more concrete. You want to use closed-ended questions.

Do you need a glass of water?

Do you want company right now or space?

Is it okay if I sit here next to you?

Closed-ended questions can actually lower the demand on the other person, and sometimes that’s exactly what needs to happen.

Plenty of everyday conversations aren’t meant to go that deeply in the first place. You’re in the elevator with a coworker or chatting with your neighbor. These moments are often about signaling, “I see you.” This connection is much simpler. There’s nothing deeper to excavate, and it’s important to recognize that closed-ended questions are great in these moments.

One aspect of mental fitness that’s important to understand is that there are different types and levels of connection you’ll have with different people in your life. It doesn’t mean those connections are any less valuable. I love checking in with my neighbor. It’s wonderful to talk to someone in the elevator or a coworker. Those are really grounding experiences.

Closed-ended questions help with those interactions. Open-ended questions are what we want to use when we’re trying to have a deeper, more meaningful conversation and understand and learn more about another person.

Building Self-Awareness Through Better Questions

What we’re building here is self-awareness: knowing that you have both tools and being able to gauge the situation and think through your strategy to better connect with the people around you.

The next time you’re about to ask, “Are you okay?” consider whether the situation is appropriate for a more open-ended question, such as “What’s going on for you right now?” And if it doesn’t feel like the right moment, trust that, too.

Understanding when to use open-ended questions to explore and when to use closed-ended questions to help stabilize things or get concrete pieces of information is an important part of learning about our communication styles.

Try it once today. The next time you find yourself running into a wall of one-word answers and want to hear a little more, take a step back and think about shifting to an open-ended question. Try starting with “what” or “where” to get a little more information about what’s going on and open that door a little wider.

For more tools like this, check out my Mental Fitness Mondays newsletter. Every Monday, you’ll get practical skills to help build your mental fitness, develop more self-awareness about your communication styles, and discover simple ways to create better connections and support your mental health.

Drew Ramsey, MD

Drew Ramsey, M.D. is a psychiatrist, author, and farmer. He is a clear voice in the mental health conversation and one of psychiatry’s leading proponents of using nutritional interventions. He is an assistant clinical professor of psychiatry at Columbia University College of Physicians and Surgeons.

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