What’s Better than Saying “Why Didn’t You…”?

Gregg Williams, MFT
3 min readDec 17, 2022
Photo: Soroush Karimi, Unsplash

There are times when you want to get to the bottom of a situation, but the person you’re talking with isn’t cooperating. You ask questions; their answers get shorter and shorter. Quite quickly, the conversation ends in deadlock. Here’s an example:

“Jamal, you got a C- in math, which is a lot worse than last semester. Why didn’t you do better?”

“I don’t know.”

“Did you study?”


“How much?”

“A lot…”

And so the conversation continues. Jamal is, understandably, defensive. It’s like pulling teeth. All Jamal wants is for you to stop talking.

But is there a way to make these conversations get results?

Here are some conversation helpers you can use.

“I’m curious about…”

The key to many conversations about problems and misunderstandings is getting more information before you proceed. “I’m curious about…” is a strong way to start a conversation. It’s a “soft” beginning. It’s nonjudgmental. Most important, it prevents defensiveness because it gives the other person a sense of control over the conversation.

“Tell me more about…”

Unsuccessful questioners use specific questions to a solution, but in a way that makes the other person feel defensive and wanting to pull away.

Successful questioners understand that unspoken details must be revealed before they can resolve the situation. Only when the situation is understood can the situation be resolved.

You can use “Tell me more about…” several times, as needed, to gain an increasingly more details about the situation.”

“What am I missing?”

You can get to a point where the other person has nothing more to contribute. So what do you do?

What am I missing?” invites the other person to keep thinking about the problem. It suggests that they know some detail that they would rather not share or that they don’t know is important. Coming at the end of a “soft” conversation that hasn’t provoked defensiveness, they “dig deeper” and often supply the detail that leads to understanding.

Putting it all together

Let’s see how the above conversation is transformed by using these three conversation helpers:

“Jamal, you got a C- in math, which is a lot worse than last semester. I’m curious about your grade changing like that.

“I’m just not good at it.”

What more can you tell me about that?”

“My teacher said I should get some help after school.”

Tell me more.”

“It helped, but I still got a C.”

“Jamal, I hear that you got better, but I’m still not understanding. What am I missing?”

“Tony and Marco kept making fun of me, so I stopped going.”

“Okay, now I understand. Don’t worry, we can fix this….”

Compare these two conversations, both of which are about the same situation. How would you feel being Jamal in the first conversation? How about the second conversation? The difference is striking.

You don’t have to use all three of these conversation helpers in a conversation. Each is helpful in its own way, and using just one can turn a difficult conversation into a successful one.

Now it’s your turn.

Your employee didn’t turn a report in on time. Imagine a conversation where you use one or more of these conversation helpers. You’ll learn something.



Gregg Williams, MFT

Retired therapist. Married 27 years. Loves board games, serious movies. Very curious about many things. Over 13,600 people are following my articles.