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How to Enjoy Small Talk and Deepen Your Conversations

The vertical questioning technique can make conversations more rewarding.

Key points

  • Disliking chitchat or having your conversations peter out quickly may indicate you are uncomfortable driving an exchange deeper.
  • If this is you, it's not your fault. Perhaps you didn't get to experience enough meaningful talk in your childhood home.
  • You can learn this technique and, with practice, deepen your interactions with others in a healthy and rewarding way.
 peopleimages/Adobe Stock Images
The vertical questioning technique opens doors.
Source: peopleimages/Adobe Stock Images

Justina recently moved to a new town and has been feeling lonely, but the task of making new friends seems daunting. She wishes there was an easier way.

Roger has very few second dates. He feels uncomfortable meeting new people and doesn’t know how to move his conversations along with others. He wonders how to form more genuine connections.

Melinda dreads social gatherings. She struggles with small talk and feels bored in casual conversations. “It seems pointless to go to these events and have dull conversations,” she thinks to herself.

Can you relate to Justina, Roger, or Melinda? If so, vertical questioning may be for you.

This simple yet incredibly effective conversational technique helps people communicate on a deeper level. This skill is especially useful for those with childhood emotional neglect.

If you grew up in an emotionally neglectful home, you’re probably familiar with a lack of communication, low emphasis on emotions, and surface-level conversations. It’s difficult to learn how to talk to someone on a deeper, emotional level because it was never modeled for you. Instead, you were taught how to communicate using facts and logistics to avoid a conversation that may elicit emotions.

Learning how to communicate using vertical questioning will allow for ease in making new friends, strengthen already established bonds, and increase the rewards of your everyday interactions with others.

Vertical and Horizontal Questioning

Both vertical and horizontal questioning involve asking questions when engaging in a conversation. But vertical questioning prods the person you’re conversing with to turn inward and think about their response more profoundly.

Vertical questioning is the key to making small talk or casual conversation much more interesting and satisfying—for you and the other person. This conversational technique creates an environment of curiosity and understanding.

Horizontal questioning seeks to uncover facts and information from your conversational exchange. These are often close-ended questions that produce a specific answer without room for elaboration.

Let’s take a look at how vertical and horizontal questioning differ:

Horizontal Questions Vertical Questions

Are you feeling OK? Why do you think you’re feeling sad?

What do you do for work? How did you become interested in your line of work?

Did you have fun on vacation? What were your favorite parts of the trip?

Where did you grow up? What was your childhood like?

Do you enjoy nature? What types of outdoor activities do you enjoy?

Horizontal questions are convenient for gathering information. When used in a thoughtful way, these types of questions can preface a vertical question. You may start horizontally and ask, “What do you do for work?” and then shift vertically with, “How did you become interested in that line of work?”

When you ask a vertical question, you get a glimpse into a person’s inner world— their history, background, feelings, desires, and preferences. That is something special. I encourage you to try it with a friend, a coworker, your spouse, or even a stranger to see what you may learn or discover.

A Horizontal Conversation Falling Flat

Bobby: I can’t believe it’s been so long since we’ve gotten together! How many years has it been?

Mary: Hmm...It has to be about eight years now!

Bobby: Wow that’s such a long time. What do you do for work?

Mary: I’m working as a pediatric nurse. How about you? Are you still in sales?

Bobby: Yep! I’m the manager of a car dealership.

Mary: That’s great! Have you kept in touch with anyone from high school?

Bobby: I really only talk to Mike, David, and Daphne every once in a while.

Mary: I remember them. I’ve been so busy I haven’t stayed in touch with many people.

Bobby: Do you work long hours?

Mary: Oh, yes. I work 12-hour shifts. It’s tiring.

While Bobby and Mary have gained some new information about one another, they are stuck in a question–answer rut. Horizontal questioning can oftentimes feel like an interrogation rather than a friendly encounter. Both Bobby and Mary have missed out on some opportunities to go vertical and discover something with a bit more substance. If they keep at this pace, the conversation is bound to flatline.

Below you’ll see how the conversation can come alive with vertical questioning.

A Vertical Conversation Going Deeper

Bobby: So you’re in the nursing field. How do you like your job?

Mary: I’m a pediatric nurse, and I absolutely love it. I’ve always adored working with children.

Bobby: That’s wonderful. What is it about working with children that you love?

(Mary answers Bobby’s question and feels engaged and open due to Bobby’s noticeable interest. Bobby learns that Mary feels passionate about helping people, especially children, due to her history of helping her parents take care of her siblings growing up. The way this conversation is going allows Bobby to share more deeply, too.)

Mary: So you work at your dad’s car dealership. What’s it like working with your dad?

Bobby: Actually, I’m running the dealership now. My dad passed away last year. I’ll be honest… it’s been challenging. Taking over a family business and grieving the loss of my dad have been difficult to manage.

Mary: I’m so sorry to hear that. How have you been balancing that?

Bobby: I make an effort to prioritize taking care of myself. I’m sure you feel similar in the nursing field. It’s easy to put yourself last when you’re taking care of other people or have such a busy schedule all the time.

Mary: I’m so happy to hear you are taking care of yourself. Maybe you can give me some tips!

Bobby and Mary are learning about one another’s passions, backgrounds, and challenges thanks to vertical questioning.

Vertical Questioning Can Be Your Superpower

Vertical questioning can rejuvenate dull exchanges with others, deepen your connections, and even reduce some social anxiety. Having this skill can boost your confidence and help you feel prepared when conversing with others. And you will no longer need to dread small talk.

Most who grew up with childhood emotional neglect struggle with communication, especially chitchat or conversations that uncover emotions. This skill requires practice and going out of your comfort zone to try something new…but it will be worth it.

Just as you might feel safer in the shallow end of the pool, you also might feel unfulfilled as you see others diving and swimming in the deep end. With these tools, you have the ability to go deeper. Jump in when you’re ready!

© Jonice Webb, Ph.D.


To determine whether you might be living with the effects of childhood emotional neglect, you can take the free Emotional Neglect Questionnaire. You'll find the link in my Bio.

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