The Art of Asking Transformative Questions Through Awareness

I wrote this blog with spiritual directors in training in mind, but the insights here can benefit anyone looking to listen more deeply, ask meaningful questions, and foster richer conversations. Whether in friendships, family interactions, or moments of guidance, how we engage with others can strengthen relationships, spark growth, and create space for a deeper connection.

Spend time with a toddler, and you’ll likely hear them say, “Daddy, watch this!” or “Look at me, Mommy!” as they proudly share their latest discovery. From a young age, we long to be seen, heard, and understood. But genuine connection goes beyond simply paying attention—it’s about engaging in ways that invite deeper reflection. While listening is important, the right question can unlock self-awareness, reveal new perspectives, and spark genuine transformation.

For spiritual directors, this practice is essential. A well-placed question creates space for exploration, deeper awareness, and an encounter with God. In the Missional Spiritual Direction Certificate Program (MSD), we’ve emphasized that the best questions aren’t meant to satisfy our curiosity as directors or to gain a deeper understanding of the situation. Rather, they help directees explore their stories for greater awareness and self-discovery. Unlike therapists, pastoral counselors, or mentors, spiritual directors don’t diagnose or analyze. We ask questions not to figure out what advice to give in the end, but to help the directee see where God is present and active in their story. By guiding their awareness, we help them recognize God's movement, inviting them to become more attuned to their inner life and His presence.

But this isn't just for spiritual directors. The ability to ask questions that promote insight and awareness is something we can all cultivate. That said, it’s essential to recognize that not everyone may be ready to engage with deeper questions. In spiritual direction, directors seek permission before inviting someone into deeper reflection, ensuring that the process is welcomed and not imposed. In everyday conversations, a thoughtful way to offer these questions is to frame them as gentle invitations rather than pointed inquiries. Instead of asking, "Have you thought about why you feel this way?" try, "Would it be helpful to explore what might be behind that feeling?" This allows the other person to engage at their own pace without feeling pressured or exposed.

Timing and openness matter. Dr. Bruce Jackson of the MSD certificate program often reminds directors that even the best question, if asked at the wrong moment or with the wrong posture, can lead to resistance rather than encouraging reflection. If someone is not in a place to process deeply or if a question feels intrusive, they may shut down or become defensive. Transformation happens in an environment of trust, not force. Rather than pressing for a response, it’s often more impactful to create a space where people feel safe and ready to engage when they are ready.

Whether guiding someone in their faith journey, supporting a friend, or simply engaging in deeper conversations, the right questions can lead to transformation. Here are some key takeaways from my experience as a spiritual director that anyone can apply to the art of asking transformative questions:

1. Shape Questions for Awareness, Not Answers

Craft questions that invite reflection rather than seeking solutions. Encourage the listener to pause and explore their feelings.

Instead of asking:

"Why do you think you feel that way?"

Try:

"What do you notice as you sit with that feeling?"

"What comes up for you when you sit with that feeling?"

2. Ask Questions That Honor the Sharer’s Experience

Questions should affirm the directee's unique journey and help them articulate their experience in their own terms.

Instead of:

"Have you been praying regularly?"

Try:

"In what ways have you been drawn to or away from prayer recently?"


"How has your practice of prayer been evolving?"

Instead of:


"Are you feeling better?"


Try:


"What have you noticed in your journey of healing?"


"What’s been shifting for you lately in how you’re feeling?"

Instead of:


"Did you have a good week?"


Try:


"What stood out to you about this past week?"


"How would you describe the week you've had?"

3. Hold Space for Silence and Mystery

Allow room for the unknown and let God’s voice emerge in the silence. Avoid the need to clarify immediately.

Examples:

"Where do you sense God’s presence in this season of your life?"

"If you could name what your soul longs for right now, what would it be?"

4. Guide the Directee Back to Their Own Inner Knowing

Trust that the directee already has the capacity to discern what the Spirit is revealing within them.

Instead of:

"Do you think God is trying to teach you something?"

Try:

"How is God showing up for you in this?"

"What is stirring in your heart as you reflect on this?"

5. Guide Without Steering

Phrase questions to open awareness without directing the conversation to a fixed conclusion.

Instead of:

"How is God challenging you in this?"

Try:

"What invitations from God do you sense in this?"

Final Thoughts: A Posture of Humility, a Host

As spiritual directors, guides, or companions on someone's spiritual journey, we are not fixers or problem-solvers. Instead, we hold space for God’s work in others' lives. I often describe my role as that of a “host,” saying, “I’m simply a host, holding space to facilitate conversations between the two honored guests—God and you—so you can reconnect. This time is not about me, but all about you and God.” Asking transformative questions is an art that requires humility, deep listening, and trust in the Spirit. The best questions don’t demand immediate answers but create sacred openings for encountering God in new ways. Let your questions be spacious and gentle, always pointing toward the divine guide.