Asking better questions can create clarity, build trust, and strengthen connection.
One of the most interesting requests from my coaching practice I’ve had lately came from one of my clients who is an engineer. Among one of his goals, he is looking to be able to ask better questions to his AI agent to get better answers. At first, this sounded like a technical skill. After all, if you want better results from AI, you need to know how to formulate an effective prompt.
But the more we talked about it, the more I realized this isn’t just an AI skill – it’s a communication skill.
We have been working together on effective communication, and asking better questions can lead to greater clarity, deeper understanding, stronger relationships, and greater trust.
Questions are not simply a way to gather information. They are a way to create connection. The best questions communicate curiosity, respect, presence, and a willingness to understand before responding.
Better questions create better conversations.
Think about the last time someone asked you a question that made you stop and think.
Maybe it was:
“What do you think we’re missing?”
Or:
“What would you do if you were in my position?”
Or simply:
“Tell me more about that.”
Those questions feel different from questions asked simply to gather information.
They invite us into a conversation. They signal curiosity. They give us permission to think out loud. And sometimes, they help us discover something we didn’t even realize we knew.
That is the power of a good question.
Questions can demonstrate that we’re listening.
We often think listening means being quiet while someone else talks. But effective listening is more active than that. Good listeners ask questions that demonstrate they’ve been paying attention:
“What makes you say that?”
“What is most important to you about this?”
“What have you already tried?”
“What would success look like?”
These questions keep us from jumping to conclusions. When we assume they already know the answer, we can unintentionally shut down the very people whose perspectives we need.
A thoughtful question opens the door to new ideas and potential solutions to problems we are trying to solve.
The best questions aren’t always comfortable.
It’s easy to ask questions when we already have an idea of what the answer should be. It’s much harder to ask when we’re genuinely open to hearing something different.
Consider the difference between:
“Don’t you think this is the best approach?”
or
“What are the potential weaknesses of this approach?”
The first may be looking for agreement. The second is looking for insight.
To be influential, leaders don’t ask questions simply to confirm what they already believe. They ask questions to expand their understanding. That requires curiosity, which becomes especially important during difficult conversations.
When we’re frustrated or challenged, our natural tendency can be to react, make assumptions, or defend our position. A question can create a pause.
Instead of “Why would you do that?” we might ask, “Help me understand what led you to that decision.”
The words are different, but the impact can be significant. One can sound accusatory. The other creates an opportunity for understanding.
And then there is AI.
My client’s original question brings us back to where we started. He wants to ask better questions of AI so he can get better answers. The same principle applies when we’re communicating with people. The more intentional we are about what we’re asking, the more likely we are to get information that helps us move forward.
But there’s an important distinction:
With AI, a better prompt can produce a more useful output.
With people, a better question can produce something even more valuable:
Connection.
A thoughtful question can create space for someone to be heard. It can surface an idea that might otherwise remain hidden. It can uncover a concern before it becomes a problem. And it can strengthen trust.
So before asking your next question, consider:
Am I asking to understand—or to respond?
Am I curious about the answer—or looking for confirmation?
What assumptions am I bringing into this question?
What might I learn if I’m genuinely open to the answer?
And perhaps most importantly: what could this question do for the relationship?
Because effective communication isn’t simply about choosing the right words. It’s about what happens between us when we communicate.
Asking better questions creates better conversations.
A well-placed question can create clarity. A thoughtful question can create trust. A curious question can create possibility.
And the right question, asked at the right moment, can create connection.
That’s the power of asking better questions.
What’s one question you could start asking more often to create better conversations?
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