Wanna go on a meaningful quest for your leadership calling? Ask questions. Then ask the Holy Spirit to help you listen to discern magnetic alignment between your heart and a particular church’s heart. When dialoguing with a new church leadership team around a new role, a prayerful Socratic Method is the best way to gain critical insights. So ask prayerful questions—focused, deep-diving, truth-exposing, insight-gaining expeditions of true curiosity. Then trust God to guide your steps (Pr 25:2).


  1. What role does Scripture play in the life of a Jesus-follower and a church?
  2. How do you define the Gospel?
  3. How do you (re)present the Gospel in/thru your church?
  4. Does your Ecclesiology drive your Christology? Or does your Christology drive your Ecclesiology?
  5. How does the Incarnation affect the way you do/be church?
  6. What is your position on Jesus’ Return?
  7. What is your position on end times? Do you teach on this or avoid it?
  8. What is your view of the role of the Holy Spirit in the life of a Jesus-follower and the church?
  9. What is your philosophy of worship? How does the weekend service intersect this?
  10. What is your perspective of women in ministry/leadership? How do you teach/practice this?
  11. What’s your position on Creation
  12. How do you define sexuality and marriage? How do you teach/engage these?
  13. What is the role of baptism in the life of a believer/the church?


  1. Tell me about the strength and depth of your elders. What is your elder model? How does it function across locations? How do you develop new and existing elders?
  2. How would your leadership/core define the word “church“?
  3. What do you hope never changes with a new pastor? 
  4. What do you think must change with a new pastor?
  5. Have leaders ever broken trust/abused power here? How was that handled?
  6. Can women be given the same spiritual gifts and roles as men?
  7. What does accountability look like with leadership?
  8. Thinking about your current or last senior leader, when was the last time a subordinate confronted them on something they said or did? How did they handle that? What does/did accountability look like to/for them?
  9. How developmental is your staff? What do you do to proactively help them maximize potential?
  10. Team: how do you ensure you bring the right balance of character and competence in leadership development?
  11. I hunger to be proactively & fully developed as a pastoral leader. If I were to join your team, how would you intentionally work to develop my competence and my character
  12. Do you have a well-developed leadership pipeline for key seats, especially the senior pastor roll? If not, why not? What are you proactively doing to change that?
  13. How transparent is your team on “shadow sides”? How well do you celebrate your “sunshine”?
  14. How do you view change—as a friend or foe? Are you simply open to it, or do you seek to drive it? (i.e., innovation)
  15. Can you describe the leadership style of the ideal lead pastor?
  16. How does your staff have fun?
  17. What would be the best way for a pastor to build trust in this culture? (staff & congregation) What do you think would be the best way for me to display trustworthiness to this team/congregation?
  18. What is leadership’s level of urgency to change and best reach others? The best time to grow urgency is when you are healthiest. What are you doing to grow urgency these days? (see my chart) 
  19. Philippians 3:10 is my holy obsession (“I want to know Christ—yes, to know the power of His resurrection and participation in His sufferings, becoming like Him in His death”). Please tell me how your church would be a community of faith that would allow me to fully realize that, or if it would be focused more on programs and getting bigger. (If it is the latter, I am not your man.)
  20. Tell me your reaction to this statement: I am not worried about going further faster as much as I am worried about going slower deeper. How about this one: My approach is to concern myself with quality and let God worry about quantityResonate or repel?


  1. Tell me the story of how this church started. (origin story is hugely formative)
  2. How clear is your church on its purpose and unique DNA? (mission & values)
  3. Does your church confuse worship and evangelism?
  4. If Jesus were to write an email (a la His letters to the churches in Rev 2-3) to your church, how would He praise or encourage you? How would He push or challenge you?
  5. What is your church’s prayer temperature? 
  6. What is your church’s invitation temperature? 
  7. How do you encourage serving? Is volunteerism linked to servanthood as spiritual formation?
  8. How do you encourage community? Does your spiritual pathway include rows and circles?
  9. Do you have a philosophy of worship? Does your CORE know it?
  10. How do you handle conflict? Any unresolved? (drill into specifics; scenarios; styles)
  11. When your CORE is cut, what do they bleed?
  12. What are the greatest tensions your families face?


  1. How do you define culture? (Beliefs + Values + Unspoken Norms = Your “Collective Soul”)
  2. How would you describe your culture? (paint a portrait of your church’s collective soul)
  3. What can you tell me about how you architect culture? 
  4. What sacred cows are there here? Or what may be in danger of becoming one?
  5. What makes your CORE/staff team laugh/cry/cheer/angry?
  6. Innovation: how well does your team proactively pursue new?
  7. Innovation: tell me about your most recent experiments? How do you handle failure?
  8. What imbalances exist in your culture? (i.e., Celebrity over Humility; Grace over Truth; Mission over Master…)
  9. Where is your culture healthyLess healthy? (see my Culture Weakness Assessment)
  10. How well does your diversity (staff and congregation) reflect the demographic diversity of your footprint(s)? (Intentional plan to address this?)


  1. What is your primary Target
  2. What is your church’s current strategic situation? (STARS Model: Start-up, Turnaround, Realignment, or Sustained Success). 
  3. COVID: What was the biggest struggle you had as a church going through COVID? What was the biggest change you made coming out of COVID? 
  4. Please tell me how you would know if your concern over building your Brand was beginning to outweigh your focus on Jesus? (Brand over Bride or Mission over Master cultural imbalances)
  5. How does your church prefer to do strategic planning? (i.e., StratOp?) What’s your rhythm?
  6. How do you define discipleship? Does your church disciple people? What is the framework/pathway for discipleship? Have you considered a Family vs Individual lens on this?
  7. How does/can your big church cultivate “small presence” for incarnational impact? 
  8. What does excellent/effective teaching look like to you?
  9. How intentionally do you discern and map out the preaching/teaching diet over time?
  10. Is there any hot-button cultural topic that is taboo or off-limits from your teaching platform? (i.e., sexual identity/gender issues; politics; abortion; racism; evolution; etc.)
  11. Do you have a statement of core beliefs? Anything need to be added/reinforced/removed?
  12. What is your governance model? Is your senior leadership fully bought in to the current model?
  13. On a 10-scale, how open are you to exploring and experimenting with new ways of church multiplication? (i.e., microsites vs megachurches)
  14. How did you select your current multisite model?
  15. What are the pros and cons of your current multisite model? (i.e., What’s your philosophy behind the video teaching model? Worship model? What operational services are centralized? Where is decentralization, contextualization, or customization encouraged? What’s your financial model?)
  16. How do you distinguish between multisite and church planting? Why do you do either?
  17. If the Church is God’s “Song,” how well is your church “singing” these days? (i.e., harmonizing its Attractional and Incarnational, Pull-In and Push-Out, Come & See and Go & Be, or Gathered and Scattered “notes”) Any changes you should make to make more beautiful ministry “music”? 
  18. What are the greatest real/felt needs of your surrounding community? Core problem/challenge?
  19. How do you ensure your ministry is appropriately and not overly complex/simple? How do you manage what I call “simplexity”? (i.e., the right dynamic tension between simplicity and complexity. Careful simplicity is so much harder than careless complexity; but it’s also so much better.) (How do you shoot for “Home Button Simplicity”? i.e., Looks simple to users, but you know there’s a lot underneath that makes it work well.) Every growing church necessarily has operational complexity; but too much complexity to congregants (i.e., too many ministry offerings and options) is paralyzing. So how can you make your growth path simple looking on the surface, while supporting it with appropriate complexity underneath?
  20. What is the financial strength of your church? (Debt? Debt retirement plan? Percentage of core who tithe? New donors? Annual stewardship discipleship plan? Budgeting/tracking process?)
  21. How well do senior leaders model generosity
  22. How well does your church steward finances? How do you do resource (re)allocation?
  23. Reputation: How does your surrounding community view your church?
  24. What does counter-culture look like in/thru your church?
  25. What does counter-catechesis look like in/thru your church?
  26. How does your church collaborate or partner with other local churches in the area? 
  27. What are you seeing in me that aligns with your church’s DNA (values, mission, vision) or strategic situation? How do you think I would bring unique strength and depth to your mission? 
  28. If strong, Spirit-led alignment exists between us, how could we together shape a role & timeline that fits my DNA/gifting/potential/family/timing and your church’s needs/future?


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