How to Master the Art of Asking Clarifying Questions

Intamateo
5 min readJul 14, 2023

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Photo by Gary Butterfield on Unsplash

In a world bustling with information and constant communication, the ability to truly understand others is a precious skill. One of the most effective ways to gain clarity and deepen connections is by asking clarifying questions. These thoughtfully crafted inquiries not only demonstrate genuine interest but also foster meaningful conversations and enhance understanding. In this post, we will delve into the art of asking clarifying questions and explore how it can transform your interactions and relationships.

Why Ask Clarifying Questions?

  • they are beneficial during job interviews in that you gain a better understanding of what you are getting into, and the interviewer will see how interested you are in the role
  • they are super rare during dates—especially from men, as I have heard—and can help you better understand and empathize with your date. This is a cheat code to a great date, by the way!
  • they are a great way to communicate with kids in that it helps show them this life skill, as well as allow you to, again, better understand and empathize with them. (See a pattern here?)
  • often, then first answer is not the deepest. When you dig down, that is where you often find the gems of understanding.

Creating a Foundation of Active Listening

The art of asking clarifying questions begins with active listening. Engage fully in the conversation, focusing on the speaker’s words, tone, and non-verbal cues. Resist the urge to interrupt or assume you understand their perspective completely. By being fully present and attentive, you lay the groundwork for asking pertinent and insightful clarifying questions.

Seek to Understand, Not to Respond

Often, we approach conversations with the intention to respond, rather than to understand. Shift your mindset to prioritize comprehension over reaction. Cultivate a genuine curiosity about the other person’s thoughts, feelings, and experiences. This mindset will enable you to ask clarifying questions that dig deeper into the heart of the matter and uncover hidden insights.

I’ve heard this put as “hold the ball. It is not your job to toss it back.” Meaning, when someone is saying something, imagine what they are saying is a ball they tossed to you, and your only job is to hold it. Don’t drop it (stop listening), don’t toss it back (tell your story), don’t change it (gaslight)—just hold it with intention. Look for a moment when they are asking for the ball back, and send it back unchanged. Meaning, reflect and paraphrase, as we will get into below.

Start with Open-Ended Questions

Open-ended questions are the foundation of clarifying conversations. Instead of asking questions that can be answered with a simple “yes” or “no,” opt for questions that encourage the speaker to elaborate and share their perspective. Examples include “Can you tell me more about…?” or “What are your thoughts on…?” These open-ended prompts invite the speaker to delve deeper and provide rich, nuanced responses.

Reflect and Paraphrase

Active listening involves reflecting and paraphrasing the speaker’s words to ensure accurate understanding. After the speaker shares their thoughts, summarize their main points in your own words and check if you’ve grasped their intended message correctly. This not only demonstrates your attentiveness but also gives the speaker an opportunity to clarify or expand on their thoughts if needed.

Use Probing Questions

Probing questions are powerful tools for uncovering underlying motivations, exploring different perspectives, or challenging assumptions. These questions encourage deeper reflection and can lead to transformative insights. Examples of probing questions include “What led you to that conclusion?” or “How do you see this situation from a different angle?” Be respectful and sensitive in your approach, creating a safe space for open and honest dialogue.

11 Thought-Provoking Questions to Ask on a First Date →

Embrace Silence

Silence can be uncomfortable, but it is also a valuable tool in the art of asking clarifying questions. When you pose a question, allow the speaker time to reflect and respond. Resist the urge to fill the silence or rush the conversation forward. Sometimes, the most profound insights emerge in moments of thoughtful contemplation.

One way to become more comfortable with the silence is to meditate. This practice can help you sit in silence and honor it.

Show Empathy and Validation

Asking clarifying questions is not solely about seeking information; it is also about fostering connection and empathy. Express genuine empathy and validate the speaker’s experiences and emotions. Let them know that you value their perspective and are committed to understanding their point of view. This creates a safe and supportive environment for open dialogue.

Here Are Seven Effective Clarifying Questions You Can Use During a Conversation

“Could you please elaborate on that?”

This question encourages the speaker to provide more details and expand on their point, helping you gain a deeper understanding of their perspective.

“Can you give me an example?”

Requesting an example can make abstract concepts more concrete and help you grasp the practical application of the information being discussed.

“Are you saying that…?”

Summarizing what you’ve understood from the conversation and asking for confirmation ensures that you’ve interpreted the information correctly.

“What do you mean by…?”

When encountering unfamiliar terms or concepts, asking for a definition or explanation can prevent misunderstandings.

“Is this the same as…?”

Comparing the current topic to something you’re already familiar with can help establish connections and clarify similarities or differences.

“How does this relate to our main goal / objective?”

This question keeps the conversation focused on the primary purpose, ensuring that the discussion remains relevant and aligned with the intended outcome.

“Could you clarify the sequence / timeline of events?”

When discussing a series of events or steps, asking for clarification on the order helps create a coherent narrative.

In Summary

Mastering the art of asking clarifying questions empowers you to truly understand others, fostering deep connections and enhancing your communication skills. By actively listening, seeking understanding, using open-ended and probing questions, reflecting and paraphrasing, embracing silence, and showing empathy, you can create meaningful conversations that uncover insights, bridge gaps, and strengthen relationships. So, start incorporating these practices into your interactions, and watch as the power of asking clarifying questions transforms your personal and professional connections.

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Intamateo

Intamateo is a collection of my learnings over the years, through 4 therapists, 3 personal coaches, 2 groups, and a shaman. I’m still exploring my insides.