10 tough questions every leader must ask themselves

By Dan Britton, Voices Contributor Thursday, September 30, 2021

One of my favorite parts about serving with the Fellowship of Christian Athletes is the opportunity to spend time with amazing ministry and business leaders from around the world. My goal is to be like a sponge while I’m around them and ask as many questions as possible. The leaders I serve alongside do the same. Their answers to our tough questions produce powerful insights, principles, and disciplines. Spending time with our global leaders makes it clear that they are also asking themselves tough questions.

Asking the right questions in the right way at the right time helps to surface what’s really going on. Great leaders are skilled with the ability to ask tough questions that reveal the truth. Great leaders don’t only ask others questions, but they ask themselves tough questions.

Notice the difference. Leaders don’t question themselves; they ask themselves questions. One is a matter of doubting, the other discovery.

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It is hard to ask yourself tough questions — to dig into your 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 tough questions that help you discover why you do the things you do. Self-examination is never found at bargain prices. There is always a significant price you will have to pay. 

The Bible is loaded with verses that challenge us to look within our soul to solidify our faith. Our faith in Jesus Christ is our foundation, and we must always make sure there aren’t any cracks. Asking tough questions forces us to look at every area of our hearts and to make sure we are not hiding or covering anything up. The Apostle 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).

This is one test every leader at every level needs to take if they want to get better: self-examination. How do you do this and where do you start? Listed below are 10 tough questions that will pull back the layers of your heart and expose the truth. They will help you get beneath the surface. As you read through each question, take some time to let it penetrate your soul before you rush to the next one. Coaches, athletes, business leaders, teachers, moms, dads, students, and pastors — we all 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 do I 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)

Leaders, you can do this. Let God have complete access to your heart and allow Him to ask you tough questions. He wants to be your foundation and get to your heart. He wants to form you into the image of Jesus Christ and help you be the kind of leader that asks others, and yourself, tough questions. Enjoy the journey!