As a leader and coach, I’m always working to improve how I ask questions—the kind that create awareness, encourage growth, and help others explore their potential more deeply. After all, great leadership isn’t about having all the answers; it’s about asking the right questions.
In my last Leadership Moment, Better Questions, Better Connections, I explored how shifting the way we ask questions can lead to richer conversations and stronger relationships. Building on that foundation, let’s dive into something many of us do without realizing its impact: asking questions that start with why.
The Problem with “Why”
Who among us has asked questions that begin with “Why?” Be honest. I admit I still find myself doing this. And for those of you wondering, “Why is he asking us this?”—see what I did there. Don’t worry, you’re not alone. Asking “why” questions is almost instinctual, and let’s face it, sometimes it’s just easier.
Here’s the thing: “Why” questions, like “Why did you do that?” or “Why did you miss the deadline?” or even the classic, “Why did you make that decision?” can come with some unintended baggage. While they might seem perfectly reasonable, they often feel judgmental or critical, even when that’s not the intent. They can put people on the defensive, forcing them to justify their actions rather than reflect on them.
Consider this: how does “Why did you think that was a good idea?” sound compared to “What led you to that conclusion?” The second option feels more curious, open-ended, and less like you’re playing the blame game. It invites dialogue and exploration rather than shutting it down with defensiveness.
Asking better questions is a skill that takes practice. Still, the impact is worth the effort—replacing “why” with more thoughtful, open-ended alternatives encourages collaboration and opens the door for meaningful dialogue.
Common “Why” Questions and Better Alternatives
- Why did you do that?
Alternative: “What led to your decision?” - Why did you miss the deadline?
Alternative: “What challenges got in the way of meeting the deadline?” - Why did you make that choice?
Alternative: “What factors influenced your choice?” - Why isn’t this working?
Alternative: “What have you noticed about what’s working and not working?”
Whether coaching a team member, mentoring a peer or having a personal conversation, framing your questions can make all the difference in creating a more supportive environment where people feel safe sharing their thoughts and experiences.
