10 Tough Questions Leaders Must Ask


"The one who trusts in himself is a fool, but one who walks in wisdom will be safe." - Proverbs 28:26


Are you willing to pay the price and ask others tough questions? Being on staff with FCA, I have the opportunity to spend time with amazing ministry, sports and business leaders from around the world. My goal is to be a sponge around them and ask as many questions as possible. Asking the tough questions produces powerful insights, but most people try to impress others by talking the entire time. Very few athletes and coaches maximize the opportunity to do what life-learners always do: Ask Questions. Be Quiet. Listen. Take Notes.

“A prudent question is one half of wisdom.”
- Francis Bacon

Asking the right questions in the right way at the right time helps to surface what’s really going on. The best leaders are skilled at asking the tough questions that reveal the truth. But very few people know how or are willing to go there.

Ask yourself tough questions. If very few leaders ask others tough questions, then even fewer ask themselves tough questions. Leaders don’t question themselves, they ask themselves questions; one is a matter of doubting, the other discovery. It is hard to dig into your own heart and discover what lurks beneath the surface. Benjamin Franklin said, “There are three things extremely hard: steel, a diamond and to know one's self.” To truly know yourself requires asking the tough questions to discover why you do the things you do. Self-examination is never found at bargain prices. There is always a price to pay. 

God wants us to examine ourselves. The Bible is loaded with verses that challenge us to look within our soul in order to solidify our faith. Our faith in Jesus Christ is our foundation, and we must always make sure there aren’t any cracks. Asking the tough questions forces us to look under every rock and make sure we are not hiding or covering anything up. Paul reminds us of this truth:

“Test yourselves to make sure you are solid in the faith. Don't drift along taking everything for granted. Give yourselves regular checkups. You need firsthand evidence, not mere hearsay, that Jesus Christ is in you. Test it out. If you fail the test, do something about it.”
- 2 Corinthians 13:5 (The Message)

Take the test! Here is one test that every leader at every level needs to take if they want to get better. These 10 questions will help you get beneath the surface. As you read through each question, take some time to let them penetrate your soul before you rush to the next one. Moms, dads, students, coaches, athletes, businessmen, teachers and pastors need to take this test!

10 Tough Questions Leaders Must Ask:

  1. Do I realize it is impossible to glorify Christ and myself at the same time? (Lead with humility)
  2. Do I lead to win over people or to win souls? (Lead with purpose)
  3. Am I doing the things I am asking others to do? (Lead with integrity)
  4. Do I pray as if nothing of eternal value will happen in the lives of others unless God does it? (Lead with prayer)
  5. Am I touching the hearts of those I lead? (Lead with transformation)
  6. What’s it like to be on the other side of me? (Lead with authenticity)
  7. Do others experience God’s love through me? (Lead with love)
  8. Am I making others better around me? (Lead with serving)
  9. Do I seek personal gain through people I lead or serve them like Christ served the church? (Lead with sacrifice)
  10. Am I allowing my leadership to produce the fruit of the Spirit in others? (Lead with excellence)

Athletes and coaches, let God ask you tough questions. Let God have complete access to your heart and allow Him to ask you tough questions. He wants to continue to get to the heart of the matter and form you into the image of Jesus Christ.

Search me, O God, and know my heart; test me and know my anxious thoughts. Point out anything in me that offends you, and lead me along the path of everlasting life.
- Psalms 139:23-24

  1. Do you ask yourself tough questions? If so, what questions?
  2. When answering the 10 questions, how was the Lord speaking to you?
  3. Which areas need some extra examination? Ask the Lord to reveal His truth into each area.
  4. Commit to becoming a great question asker. Learn the art of asking the right questions.
  • 2 Timothy 3:16

  • Proverbs 1:5

  • Proverbs 9:9


“Lord God, I want to be a life-learner. Help me to be quick to listen and slow to speak. I have a long way to go, but I desire to learn from You and others. Give me a teachable spirit. In the name of Jesus, I pray. Amen.”

Bible Reference: 
2 Timothy 3