In my post yesterday about shifting from "why" to "what" questions, I explored how this simple change can transform leadership conversations. Today, I want to focus on one specific question that came up in a related Coaching for Leaders podcast episode with Elizabeth Lotardo:
What have you already tried?
What makes this question so powerful?
When someone comes to you with a problem and you ask, "What have you already tried?" you're sending several key messages simultaneously:
You expect initiative. You're not surprised that they've already taken action—you assume it. This presumption of capability builds confidence.
Experimentation is valued. By asking what they've tried, not what they've done, you're acknowledging that not everything works on the first attempt. And that's okay.
Their attempts matter. Even if their experiments didn't solve the problem, the learning from those attempts is valuable information worth discussing.
The psychological safety connection
This question creates psychological safety in a way few others can. It tells your team member:
"I don't expect you to have all the answers before you start. I expect you to try, learn, and iterate."
Contrast this with common alternatives:
- "Have you tried X?" (implies they should have thought of your solution)
- "What do you think you should do?" (puts pressure on them to have the right answer)
- "Why didn't this work?" (focuses on failure rather than learning)
"What have you already tried?" honors their agency while opening space for collaborative problem-solving.
The immediate impact
Here's what I've noticed when I consistently ask this question:
People come to me earlier in their problem-solving process, not just when they're stuck. They're not afraid to share their failed experiments because they know those attempts are part of the conversation, not evidence of incompetence.
The conversation naturally shifts from me solving their problem to us building on what they've learned. I might say, "Interesting that approach X didn't work—what did that tell you?" or "You've tried A and B—what feels like the next logical experiment?"
Asking this question consistently helps you (re)shape your organizational culture.
Your homework
So, when someone brings you a challenge, resist the urge to immediately offer solutions or ask what they think they should do. Instead, try: "What have you already tried?"
Then listen. Really listen to what they've learned. Build from there.
You might be surprised at how much problem-solving has already happened—and how much permission this simple question gives your team to keep experimenting.