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40 Leadership Questions

I am in a formal accountability relationship with five pastors whom I pursue to speak into all areas of my life. Four of them focus in specific aspects of my life.


  1. Leadership
  2. Marriage and Family
  3. Theology and Personal Revival
  4. Professional
The fifth is my local pastor who looks holistically into my life as well as ask personal purity questions. I am in community with him and serve on his eldership team.


Today I conversed with Dr. Bruce Wesley who pastors an Acts 29 church, Clear Creek Community Church in League City, TX (Houston). He provided me with forty questions on leadership that I wanted to pass along. We spent an hour discussing the section on self leadership. It was a fascinating and revealing session. Perhaps you could use them to develop other leaders.
Leadership Accountability Questions
Self Leadership

  1.   How are you unique? (calling, gifts, passions, personality, experiences, sin patterns)
  2.   How do you stay inspired? How often do you practice this?
  3. How do you preach the gospel to yourself?  (What’s the message in your mind?)
  4. What are the rhythms of grace in your life? (scripture practices, worship, community, Sabbath)
  5. What idols are calling for your worship? 
  6. How do you forsake each idol?
  7. What are the lies that you believe in your head?
  8. How is the gospel applied to those lies?
 Interpersonal Leadership
  1. Who gets you and why? Who are your guys? (2 Timothy 2:2)
  2. Who do you pray for?  What are you praying for them?
  3. Who are you considering to become one of your guys and what is your plan?
  4. Are you telling the “truth in love” to your guys, consistently?  When do you tend to “spin” something?
  5. Are you “on time” and following through with promises?
  6. Do you say “yes” and “no” with clarity? Who are the people you tend to “please” and why?
  7. How are you discipling each of your children and your spouse?
  8. Who KNOWS you?
 Organizational Leadership

  1. What mission and vision has God entrusted to you?
  2. Are you aligned to this mission and vision?
  3. To what extent is your identity wrapped up in your position or your mission?
  4. Where is there “sideways energy” in your life (schedule)?
  5. Do people in your organization know with clarity what you expect of them?
  6. What do you expect of others in your organization?
  7. How do assure that each person under your charge connects expectations to mission?
  8. In what ways do you personify vision and values?
  9. What opportunities did you decline for the sake of mission, vision or values?
  10. What are the stories that define the culture of your organization?  How do you capture these stories?  How are the stories being shared?
Team Leadership

  1. Who is your team?  (Roles, Styles)
  2. Who is going to replace you?
  3. How do you demonstrate your love for each team member?
  4. What dysfunctions on your team are you addressing?
  5. With whom do you sense the most synergy?  How can you maximize that?
  6. With whom do you sense the least synergy?  Why? How are you minimizing that?
  7. Who do you struggle to trust?  Why?  Do you address issues of trust with them?  Why or why not?
  8. What inspires each team member?  (Ask each one, “What aspect of your work brings you the most joy?  What stories do you tend to tell most often?)
  9. Do team members feel empowered to exercise their greatest gifts and talents on the team?
Pastoral Leadership

  1. What does faithfulness in your calling look like for you?
  2. In what new areas are you learning to apply the gospel?
  3. Describe your system for managing your availability and “interruptability.”
  4. How do you develop men by involving them in ministry and making decisions?
  5. What opportunities have you had / taken to herald the gospel in serving others?