Why ‘Why’ is Hurting Your Conversations - And What to Ask Instead

👋 Hi friends,

If you’ve been following along, you know I’ve been diving deep into everyday habits that either build empathy—or block it. This time, I’m zeroing in on a single word we use all the time, often without thinking: “why.”

It’s a question that can spark insight… but also one that can send us spiraling into judgment and shame—especially when it’s the first word in a sentence spoken to us.

It leads us to bob and weave, answering in circles rather than opening up. If you want to really get at the truth, ask “why” without using the word “why.”

I learned this lesson years ago in my moderator training with Naomi Henderson at the RIVA Institute. She taught me that “why” is the one question word we should almost never use in interviews. It’s not because curiosity is bad—it’s because “why” makes people feel like they’re under a spotlight. Or worse, like they’re being cross-examined.

Here’s the video version of this edition:

📚 It Starts Early

Think back to when you were a kid. Maybe you drew on the wall in marker, played ball in the house, cut your sister’s hair. What was the first thing a parent or teacher said?

“Why did you do that?” is what we are often asked by someone with power over us.

The question isn’t really an invitation to explain. It is a cue that you need to provide a rational explanation or you were in trouble. You squirm and come up with something plausible that may or may not be the whole truth. Fingers crossed that it is accepted and you are excused.

Any time punishment is involved, it builds a powerful association between behavior and outcome. Being punished isn’t something we often want to repeat so we build an almost ‘reflex’ reaction when we hear the word “why.”

This follows us through to school and into our adult life. So even as adults, when someone leads with “why,” our brains often leap straight to defensiveness.

Think about all those times you’ve been asked “why” and how it makes you feel? It can be triggering and put us on our heels, so to speak. That is the ‘why cycle’ in motion.

As a result, as parents, we miss the opportunity to teach our child how to avoid incidents that could get them in trouble. As managers and leaders, the same is also true — we are missing opportunities to coach and mentor because we are putting ourselves at odds with each other rather than being on the same side.

🧠 The Inner Critic’s Favorite Word

This ‘why’ cycle happens inside our own heads, too.

When something goes wrong, our inner critic loves to swoop in with questions like:

• “Why did you say that in the meeting?”

• “Why didn’t you speak up?”

Before you know it, you’re in a cycle of abuse, beating yourself up instead of looking for solutions. You’re stacking evidence against yourself.

This is what the person who attended my talk was referencing. For them, “why” becomes less about curiosity and more about proving a case against themself. In this case, “why” doesn’t help you grow; “why” keeps you stuck.

💬 What to Say Instead

Whether you’re talking to someone else or to yourself, you can still get to the heart of things—without using “why” as your first move.

Naomi taught me to rephrase questions using “who,” “what,” “where,” “when,” and “how” instead of “why.” You are intending the same thing but using words that don’t put someone on the defensive.

For example, try:

• “Help me understand what led you to that choice.”

• “What was going through your mind at the time?”

• “How can we approach this differently next time?”

Shifting from “why” to using the other words keeps the conversation open and forward-focused.

As a manager or leader, you want this as you will gain more understanding and truthful perspective from your team.

If you are a parent, try it out with your kids. One mom wrote me several years ago after reading my book and shared how she was faced with a decision on how to confront her child over a bad report card. She opted to say “tell me more about…” instead of her usual '“why.” The result was an open dialogue where she was able to actually help her son rather than be at odds.

Why don’t you give it a try?

Or should I rephrase it and say “what would it be like to try this out?”

Quick Recap
✅ “Why” can trigger defensiveness—internally and externally
✅ Childhood conditioning makes “why” feel like a challenge, not curiosity
✅ In your head, swap “why” for “what” and “how” questions
✅ In conversation, reframe “why” into open-ended invitations
✅ Give “Whyless Wednesday” a try this week

📣 Your Turn
What happens when you take “why” off the table for a day? Email me or hit reply—I’d love to hear your stories.

Until next time,
– Rob

🕊 May you find the courage to ask questions that open doors, not builds walls.

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Reading Between the Lines delivers of-the-moment insights into empathy and human behavior; expect practical tips on using the skill of empathy in everyday life and exclusive updates to keep my community close. All on a biweekly basis.