L2 COACHING TOOL BOX
Powerful Questions for Strategic Conversations
These questions are designed to help coaches facilitate meaningful conversations and guide members toward greater insight and intentional growth. The goal is to help leaders think more deeply, gain greater clarity, and become more visionary in their leadership. Use them as prompts, not scripts. Listen carefully and follow the conversation where it naturally leads.
QUESTION CATEGORIES:
Clarity, Perspective, Vision, Evaluation, Growth, Calling, Action, and Reflection
Questions for Clarity
When a member is uncertain or struggling to define the issue.
Why is this important to you right now?
What caused you to choose this topic?
What are you hoping to accomplish?
What would success look like?
What problem are you really trying to solve?
What question are you trying to answer?
What would happen if nothing changed?
What would happen if everything changed?
Questions for Perspective
When a member feels stuck or is focused too narrowly.
What might you not be seeing?
What assumptions are you making?
What would an outsider notice?
What would your students say?
What would your volunteers say?
What would your pastor say?
What would God possibly be inviting you to consider?
What opportunities may be hidden within this challenge?
Questions for Vision
When helping a member think bigger and farther ahead.
What could this look like three years from now?
What could this look like five years from now?
If there were no obstacles, what would you pursue?
What future opportunities excite you most?
What are you preparing for?
What are you not preparing for that you should be?
What needs to happen today to create that future?
What legacy are you hoping to leave?
Questions for Evaluation
When helping a member assess a ministry, strategy, or situation.
What is working well?
What is not working?
What needs to be strengthened?
What needs to change?
What needs to stop?
What is producing the greatest impact?
What is consuming energy without producing results?
Where are the greatest opportunities for improvement?
Questions for Growth
When helping a member focus on personal development.
What is God teaching you right now?
What area of growth requires your attention?
What fear may be holding you back?
What conversation are you avoiding?
What truth do you need to face?
What habit needs to change?
What would growth require of you?
What would courage look like in this situation?
Questions for Future Calling
When helping a member think about the next chapter of leadership.
What excites you most about the future?
What concerns you most about the future?
What strengths should you continue developing?
What experiences do you still need?
What opportunities should you explore?
What doors seem to be opening?
What doors seem to be closing?
What might God be preparing you for next?
Questions for Action
When helping a member move from insight to action.
What is your next step?
What is the most important next step?
What obstacle might get in the way?
How will you address that obstacle?
Who needs to be involved?
What commitment are you willing to make?
How will you measure progress?
What should we revisit during our next conversation?
Questions for Reflection
At the end of a coaching session.
What did you learn?
What surprised you?
What changed?
What became clearer?
What still needs attention?
What are you most grateful for?
What would you do differently?
What is God inviting you to pursue next?
Tips for Coaches
Resist the temptation to immediately provide answers.
Create space for discovery.
Create space for reflection.
Create space for vision.
The member owns the growth.
The coach facilitates the growth.
Your role is not to think for the member.
Your role is to help members think more deeply and strategically than they could alone.
PRO TIP: The quality of the coaching conversation is often determined by the quality of the questions being asked.
Author: Bo Boshers • Posted: August 2026