Based on insights from John Certalic (Episode 98 of “You Were Made for This”)

We’ve all heard the phrase, “It never hurts to ask.” It’s often used to encourage boldness, persistence, and the belief that if you don’t ask, you don’t receive. But is that really true? In his podcast, You Were Made for This, John Certalic challenges this common wisdom and explores how, in reality, asking can sometimes cause harm to our relationships.

Why “It Never Hurts to Ask” is a Myth

In some cultures, asking personal questions is considered inappropriate or intrusive. Rather than deepening connections, it can create distance. Here are a few reasons Certalic gives to why people might be hesitant to answer questions:

• Fear of judgment (e.g., “Are you getting the COVID vaccine?”)
• Concern that their answer may be used against them (e.g., “How much did you pay for that car?”)
• A preference for privacy, whether due to personality or upbringing
• A desire to maintain relational boundaries

The Consequences of Asking Thoughtless Questions

The questions we ask shape how people perceive us. While sometimes a bold question can open doors, it can also make others feel:

• Defensive or manipulated
• Violated or exposed
• Pushed in a direction they don’t want to go

This is especially true in close relationships, where trust and sensitivity matter most.

When It Does Hurt to Ask: Real-Life Examples

Certalic shares two compelling examples of when asking a question did more harm than good:

1. The IT Professional Who Asked Too Much
• A man gave notice at his job and then asked his employer to pay for a training course before his departure. He believed, “It never hurts to ask,” but his request damaged his credibility and could affect future references.
2. James and John’s Mother in Matthew 20:20-28
• She asked Jesus to give her sons seats of honor in His kingdom. Her request violated cultural norms and alienated the other disciples, setting up unnecessary competition and resentment.

A Better Approach: Thoughtful Asking

Certalic challenges that before asking a question, consider:

• What is my motive? Am I seeking personal gain, or is my request genuinely beneficial?
• How will others perceive my question? Will it create distance or build trust?
• What does this question reveal about my character?
• How will I use the answer?
• Is this the right time to ask?

The IT professional’s timing was poor, and the mother of James and John asked at a moment when Jesus had just spoken of His impending suffering. Timing matters.

A Final Takeaway: Let Honor and Humility Lead

Instead of aggressively pursuing what we want, we should put ourselves in positions where opportunities come to us naturally. If something is meant for us, it will be offered in God’s timing, not forced by our insistence.

Bottom Line: Be mindful of the implications of your questions. The closer the relationship, the greater the potential for harm. Asking the wrong question at the wrong time can drive a wedge between you and others, damaging trust and connection. At HCA we strive to teach students to ask good questions, we are also striving to have them ask thoughtful questions filled with love.

For more insights on relational intelligence, listen to John Certalic You Were Made for This podcast. His wisdom offers a practical and biblical approach to navigating relationships with grace and thoughtfulness.