Engage and Connect by asking Good Questions

​Asking good questions is a key part of engaging and connecting with people. Your ability to ask questions will determine how much information you’re given and the connection you will make with your audience.
What’s the key to asking good questions? Many people learn from their teachers to ask memorization and recall based questions that don’t provide much connection, stimulation or information.
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The Problem with Recall-Based Questions

• They limit expression. Recall questions demand “right answers,” discouraging unique perspectives.
• They stifle connection. When people feel quizzed, they are less likely to open up.
• They overlook context. Facts alone rarely capture lived experience, motivation, or emotion.

In practices like coaching and speaking, most questions are aimed at gaining personal information and understanding of the recipient. Their personal story and experiences are what you really want to know, and what will be helpful in developing their skills. Asking questions can be a great way to gauge familiarity and understanding of a topic.

• What does X mean to you?
• What is your experience with X?
• How would you define X in your own words?

Questions can also be used to summarize information or review what you’ve gone over. Focus on engaging and connecting with your questions, instead of quizzing people on information. Practice using questions that begin with what because they elicit a descriptive answer.

The Case for Connection-Based Questions

• They build trust. Asking about personal experiences signals genuine interest.
• They reveal insight.  Stories, perspectives, and emotions often carry more learning value than factual responses.
• They guide development. In coaching or leadership, understanding someone’s “why” is more powerful than confirming their “what.”

 
When asking more emotion related questions, try asking how someone feels instead of putting words in their mouth by asking “do you feel this way?” Trust they will have the answer.
Asking questions is all about letting the other person lead with their thoughts, opinions, experiences or emotions. Inserting your own bias or experience may block them from fully expressing their thoughts.

• How does that make you feel?
• What are your thoughts about that?
• What kinds of things come up for you when X happens?

Asking good questions is more than a communication skill, it is a leadership tool. The ability to move beyond surface-level questioning and into authentic, curiosity-driven dialogue allows leaders, coaches, and speakers to foster trust, unlock insight, and create lasting impact. When you lead with questions that invite meaning, experience, and emotion, you don’t just collect information you build stronger, more authentic relationships.

Written by Danny Socwell
Marketing Director at STAND TALL
[email protected]