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Do You Find Yourself Fighting to Listen? 5 Questions to Help You Re-Engage & Show People You Care

Leaning into a conversation to listen with great intentionality is one of the best ways to let people know you care about them. 

Self-focused individuals, on the other hand, make terrible listeners for one reason alone: they need to be the center of the conversation. Their stories and comments let everyone know they think they are the most important person in the room. This deflects a following versus attracting one. The casualty of such actions will always be the loss of influence. 

Because selfless people put themselves behind others, they make the other person the most important person in a conversation. They ask questions and then wait for answers. 

Steve Wiley of the Lincoln Leadership Institute is fond of saying, “Listen until it hurts.” It takes effort and concentration to give someone your undivided attention. It is even harder for those of us who fight selfishness in our character. But, what a powerful gift to offer others. 

To listen until it hurts takes a level of Humility and Selflessness which can only be acquired through practice. How do we grow in this area? By utilizing questions which hold a “tell me more” approach.

Such questions may sound like: 

  • What other factors contributed to that?

  • What happened next?

  • How did it make you feel?

  • What hopes did you have?

  • What do you wish had happened differently? 

To be a Leader of Character, we must DO what we want to BE. If we want to be selfless, we need to choose to ask more questions and listen longer.

Dig Deep Questions

  • Why is it selfish when we talk more than we listen?

  • What questions can we use in conversation which offer a “tell me more” approach

  • Who could you initiate a selfless conversation with this week? 

  • In what situations do you find yourself fighting to listen?

  • What conversations are coming this week where you can practice selfless listening? 

Making a shift towards taking responsibility and living with Selflessness is a lifelong journey and we want to partner with you through it. The Habits of Character Action Guides provide 6 months of daily, interactive training. 

Every month, you and your team focus on one specific habit of character based off of Dave Anderson's Becoming a Leader of Character book. These habits include: Courage, Humility, Integrity, Selflessness, Duty and Positivity. 

Get your FREE one-week guide with five Courage Workouts here and be the first to dive into the Character Action Guidebooks. For more resources and tools go to

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