Stop asking 'Why?' and start asking what matters
I've sat through thousands of conversations in my twenty-five years of teaching, coaching, and pastoral care.
And I've learned this: The wrong question can destroy a conversation. The right question can save a life.
Most of us have never been taught how to ask good questions. We default to the ones that feel natural—but natural doesn't mean helpful.
Today, you'll learn the difference.
The Worst Question
Let me start with the question you need to stop asking:
"Why?"
"Why did you do that?" "Why didn't you study harder?" "Why do you feel that way?" "Why can't you just...?"
Here's what "why" communicates to the person you're asking:
Defend yourself. Justify your choices. Prove to me that you're not stupid or lazy or wrong.
"Why" sounds like curiosity. But it almost always lands as judgment.
The Athlete Who Shut Down
Early in my coaching career, an athlete missed a height she should have cleared easily. She walked back to me, clearly frustrated.
I asked: "Why did you miss that?"
She shrugged. "I don't know."
I pushed: "But why did you hesitate on your approach?"
"I said I don't know."
Conversation over. She shut down completely.
What I meant: "I'm trying to help you figure this out."
What she heard: "You're disappointing me and I want you to explain why you're failing."
The Better Questions
Years later, different athlete, same situation.
This time I asked: "What happened on that jump?"
Not why. What.
She thought for a moment. "I got in my head about my steps. Started counting instead of feeling."
"What were you thinking about?"
"That I might hit the bar. That everyone's watching."
"What do you need from me right now?"
"Just... remind me I can do this."
Same situation. Different question. Completely different conversation.
The Five Question Types That Transform
1. Open-Ended Exploration: "Tell me about..."
Instead of: "Did you have a good day?" Try: "Tell me about your day."
Why it works: Invites narrative instead of yes/no. Gives them control of what matters.
Example: "Tell me about what's making you anxious about this presentation."
2. Feeling-Based Inquiry: "What was that like for you?"
Instead of: "Why did that upset you?" Try: "What was that like for you?"
Why it works: Acknowledges their experience without requiring justification. No defense needed.
Example: "What was it like when your boss said that in front of everyone?"
3. Future-Focused: "What do you want?"
Instead of: "Why can't you make a decision?" Try: "What do you want to happen?"
Why it works: Moves from past problems to future possibilities. From stuck to moving.
Example: "What do you want this relationship to look like?"
4. Clarifying Invitation: "Help me understand..."
Instead of: "That doesn't make sense." Try: "Help me understand what you mean."
Why it works: Positions you as learner, them as expert. No judgment implied.
Example: "Help me understand why that moment mattered so much to you."
5. Deepening Follow-up: "Tell me more about that."
Instead of: Jumping to the next topic Try: "Tell me more about that."
Why it works: Signals that what they just said matters. Invites them deeper into their own thinking.
Example: They mention feeling lonely. You say: "Tell me more about that loneliness."
The Questions That Create Shame
Some questions are conversation killers. They shut people down, create defensiveness, or generate shame:
❌ "Why didn't you...?" (Implies they should have) ❌ "Don't you think...?" (Leading question disguised as inquiry) ❌ "Have you tried...?" (Assumes they haven't thought of obvious solutions) ❌ "What's wrong with you?" (Judgment masquerading as concern) ❌ "Why can't you just...?" (Minimizes their struggle)
These questions all share something in common: They position the asker as superior and the answerer as deficient.
The Classroom Transformation
I teach question-asking in my communication classes through role-play.
Student A shares a struggle. Student B asks questions.
First round: They ask natural questions. Usually lots of "why" and "have you tried" and "don't you think."
Student A reports back: "I felt judged. Like I had to defend myself."
Second round: They use transformative questions. Only "what" and "how" and "tell me about."
Student A reports: "I felt heard. Like they actually wanted to understand, not fix me."
Same scenario. Different questions. Completely different experience.
The Questions That Go Deepest
After 25 years, here are the questions that consistently crack conversations open:
"What's the hard part?" Gets past the surface problem to the real struggle.
"What are you most afraid of?" Names the fear that's driving everything.
"What do you need?" Direct. Simple. Powerful.
"If you could say anything right now without consequences, what would you say?" Creates hypothetical safety for truth-telling.
"What would it look like if this worked out?" Shifts from problem to possibility.
"What's one small step you could take?" Moves from overwhelm to action.
"How can I help?" Only ask if you genuinely mean it.
The Student in Crisis
A student came to my office in tears. Family emergency. Falling behind in classes. Didn't know what to do.
Old me would have asked: "Why didn't you email me sooner?" (Judgment disguised as question)
Instead, I asked: "What do you need right now?"
"I need someone to tell me I'm not failing at everything."
"You're not failing at everything. You're handling a crisis and still showing up. What would help you get through the next week?"
"An extension on the paper.”
"You have the extension. And I believe you can do this. What else?"
The right questions created space for her to identify what she actually needed, which wasn't advice or solutions, but acknowledgment and time.
The Practice
Today's challenge:
Ask five transformative questions in your conversations.
Before you ask any question, pause and ask yourself:
Am I asking this to understand, or to judge?
Does this question invite them deeper or put them on defense?
Am I positioning myself as superior or as curious?
Replace:
"Why?" with "What?"
"Have you tried...?" with "What have you tried?"
"Don't you think...?" with "What do you think?"
"Why can't you...?" with "What's making this hard?"
Then ask. And listen to how they respond differently.
What You'll Learn
Good questions don't just get better answers.
They create different conversations entirely.
They invite people into their own wisdom instead of defending against your judgment.
They open doors instead of closing them.
The question you ask shapes the answer you receive.
Choose wisely.
Tomorrow: "Listening Lesson #9: Listening Across Difference (When You Disagree)"
What's a question someone asked you that changed how you saw something? What made it powerful?
Dr. Tom Lobaugh teaches communication, listening, and ethics at Boise State University, coached high school track and field for 20 years, and is completing his PhD in Psychology with an emphasis in Performance. Learn more at tomlobaugh.com