The Art of Asking Questions: A Guide to Building Meaningful Conversations

Mara Schmitman
4 min readApr 25, 2023

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Part 1: The Importance of Asking Thoughtful Questions

Asking the right questions can lead to meaningful and transformative conversations. Whether it’s in a professional or personal setting, asking thoughtful questions can deepen our understanding of others, broaden our perspectives, and create stronger connections.

As Carl Rogers, a renowned psychologist, once said, “The curious paradox is that when I accept myself just as I am, then I can change.” This quote emphasizes the importance of being curious and open-minded when asking questions. By accepting ourselves and others as they are, we can ask questions that spark growth, learning, and change.

However, asking thoughtful questions is easier said than done. Many of us struggle to ask questions that go beyond the surface level and truly delve into someone’s experiences and perspectives. To become better questioners, we must first understand why asking thoughtful questions is important.

When we ask thoughtful questions, we demonstrate a genuine interest in the other person. We show that we value their thoughts and experiences and are invested in building a relationship with them. This can lead to greater trust, respect, and understanding between individuals.

Additionally, asking thoughtful questions can help us gain new insights and perspectives. When we ask questions, we invite others to share their unique experiences and viewpoints, which can broaden our own understanding of the world around us. This can lead to new ideas and solutions to problems that we may not have considered otherwise.

On the other hand, asking surface-level or judgmental questions can lead to a shallow and unproductive conversation. These types of questions can make the other person feel uncomfortable or defensive, which can create a barrier to true understanding and connection.

In conclusion, asking thoughtful questions is a crucial aspect of building meaningful conversations. By demonstrating a genuine interest in others, inviting new perspectives, and avoiding judgmental questions, we can deepen our understanding of ourselves and the world around us.

How to Implement a Curiosity-Driven Environment in Your Company

  1. Encourage a culture of curiosity: Encourage employees to be curious and open-minded when asking questions. Foster an environment where it’s safe to ask questions and share ideas.

Here are a few specific ideas:

  • Hold regular team-building activities that encourage employees to get to know each other and share their ideas and perspectives. This can help create a more open and collaborative environment where employees feel comfortable asking questions and sharing their thoughts.
  • Create a “question of the day” or “question of the week” where employees are encouraged to ask thoughtful questions related to their work or the company. This can help build a culture of curiosity and encourage employees to think critically about their work and the world around them.

2. Train employees on effective questioning techniques: Provide training on how to ask open-ended and non-judgmental questions that encourage conversation and reflection.

Examples of effective open-ended questions include “Can you tell me more about that?” or “How did you feel when that happened?” These types of questions encourage the person to share more about their experiences and can lead to deeper conversations. Non-judgmental questions are those that do not imply a particular answer or opinion, such as “What do you think about the situation?” or “How would you approach the problem?” These questions encourage the person to share their own thoughts and ideas without feeling judged or criticized.

3. Create opportunities for meaningful conversations: Provide opportunities for employees to have meaningful conversations, such as regular one-on-one meetings or team-building activities.

4. Encourage active listening: Encourage employees to actively listen to others and show empathy and understanding.

To encourage active listening, you can try the following:

  • Encourage employees to ask follow-up questions to clarify their understanding of what the other person is saying
  • Provide training on active listening techniques, such as summarizing what the other person said or asking for confirmation
  • Create a culture of respect and openness, where everyone’s opinions and perspectives are valued
  • Model active listening behaviors yourself, so that employees can see the importance of this skill in action

5. Provide feedback: Provide feedback to employees on their questioning techniques and encourage them to continue to develop their skills.

By implementing these steps, a company can create a culture of meaningful conversations that fosters growth, learning, and understanding.

Stay tuned for part two of this article, where we will explore the different types of questions and how to ask them effectively.

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