Asking Questions with Purpose: Coaching Beyond Comfort

Coaching is about creating space for discovery and transformation. Coaches listen deeply and ask questions to guide clients toward meaningful insights. But sometimes, conversations become unfocused, and coaches rely on habits rather than intentional techniques. This can lead to sessions filled with repetition rather than real progress. By asking questions with purpose, coaches can create clarity and direction that move their clients forward.

From Summarizing to Directing the Conversation
One of my mentees faced a common challenge: his client talked a lot, veered off in different directions, and made it difficult for him to follow the conversation. To regain clarity, he relied on summarizing what the client had said. While this approach bought him time, it didn’t always advance the session.
Instead of repeating everything, I suggested a more effective alternative: “Given all that, what would be the best use of our time today?” This question acknowledges the client's thoughts while steering them toward focus and action. Rather than getting stuck in restating information, it invites the client to identify what truly matters, allowing the session to gain momentum.

Comfort Questions vs. Intentional Questions
Many coaches fall into the habit of asking comfort questions—questions they’ve learned in coaching school that feel safe but don’t necessarily serve a purpose. They ask these questions because they are familiar, not because they drive the session forward.
However, coaching is most effective when questions are asked with intention. Every question should have a purpose, whether it’s to clarify, challenge, or deepen insight. Just as legendary violinist Itzhak Perlman once noted that some musicians use comfort vibrato—applying vibrato simply because it’s a familiar technique rather than a necessary one—coaches must ensure they are asking questions that serve the moment rather than relying on habit.

Listening Beyond Words
A coach’s role is not just to listen to words but to listen beyond them. This means tuning into emotions, identifying limiting beliefs, and recognizing patterns that might be invisible to the client. By forming hypotheses based on these observations, coaches can test insights that either resonate with or challenge the client’s assumptions.
Some insights require direct confrontation, while others call for subtlety. The depth of the coaching relationship determines how direct a coach can be. But whether a coach approaches with caution or boldness, the goal remains the same: uncovering the deeper truth that leads to transformation.

The Importance of a Clear Goal
A coaching session without a clear goal is like sailing without a compass. When a client brings multiple concerns, the conversation can easily drift. Instead of exploring everything, coaches can help clients focus by asking, “You’ve brought up these four things—what is the one issue that, if solved, would make the biggest difference?” This approach helps clients prioritize, making sessions more structured and impactful.

Conclusion: Coaching with Clarity and Purpose
Coaching is most powerful when guided by intention. Instead of relying on comfort questions, coaches should focus on purposeful inquiry that clarifies, directs, and challenges. By ensuring that each question serves a role in the client’s journey, coaches can transform their sessions from routine conversations into meaningful explorations that drive real change.