Do You Have Questions about Asking Questions?

by | Apr 8, 2024 | Blog

As a new Florida state prison volunteer, I had questions. The volunteer training, however, taught me not to ask an incarcerated man questions about the crime (s) he committed. This raised another question for me. Why am I not supposed to ask an incarcerated man those questions? I learned why and I’ll explain below. Do you have questions about asking questions?

In their book Leading with Questions: How Leaders Discover Powerful Answers By Knowing How and What to Ask, Michael J. Marquardt and Bob Tiede have a chapter titled Why We Have Trouble Asking Questions. They list four primary reasons we have difficulty asking questions: we avoid questions to protect ourselves; we are often in a rush; we lack skills in asking or answering questions; and we find ourselves in settings that discourage questions.

The fourth reason pertains to my question about why I am not supposed to ask an incarcerated man why he is in prison. Another question came to mind: how can I build a relationship with the man if I can’t ask the question why? By talking about other matters. Where are you from? How long have you been in? Are you married? Do you have children? What did you do for work? What dreams do you for when you are released?

Most new volunteers want to know why a person is in prison. It’s a natural question to ask as an outsider. Learning to befriend an incarcerated person without the why question is a learned skill just as asking questions is a learned skill. After two years of volunteering, I am comfortable relating to a man without asking the why question. I get to ask a bunch of other questions in the course of building a friendship.

Asking the why question puts the man on the defensive. It puts the crime in the forefront of the conversation instead of the person. I volunteer to befriend the men in the Toastmasters Club (called Gavel Club in prisons) and when I preach in the chapel services. They know I know they  committed crimes.

Toastmasters is an international leadership development organization where leaders are made with a special focus on public speaking. Its educational program begins with an Icebreaker speech by a new member. The person introduces themself to the club. They can do this however they choose. The new members of the Phoenix Gavel Club at Walton Correctional Institution usually include descriptions of the lives they led and the crime (s) for which they are incarcerated. I don’t have to ask them the question why.

Easter morning I sat next to man in the chapel before the service began and I preached. It didn’t take long for him to tell me what was on his mind. His 23-year old son overdosed two days prior. The son’s mother called 9-11 and the dispatcher talked her through CPR until the ambulance arrived. A very important follow-up question was his son’s name. Same as the father. I get to pray for this family without knowing what crime the father committed.

The authors of the book mentioned above believe business leaders lead best by modeling the skill of asking questions. This skill increases trust, collaboration, curiosity, new ideas, and motivation. Likewise, skillfully asking questions can improve marriages, parenting, educational enthusiasm, and volunteering experiences. Do you have questions about asking questions? I recommend the book. Bob Tiede sends out a free Leading with Questions email with guest presenters. Visit his website for more information ( What questions do you have for me?





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