7 Good Questions to Shepherd Leaders in their Spiritual Life

We are first Christians by faith through grace, our (spiritual) leadership follows by calling through gifting. The order of priority helps us live out our values.

It’s true that leadership is influence and we all have influence, but it must be activated by exercising our calling and using our gifting for the purpose of advancing God’s Kingdom.

This post is in reference to activated Kingdom influence. Your influence, God’s agenda.

Since we are first Christians, the continued development of our faith needs to be held in tandem with our development of leadership skill.

I’ve always found it noteworthy that the one thing that frustrated Jesus the most is our lack of faith. Story after story in the New Testament reminds us of this observation.

One story I reread today was about the dad that brought his son to Jesus for healing from demonic induced seizures, because the disciples couldn’t do it. This clearly frustrated Jesus. (See Matthew 17:14-20) When the disciples asked why they couldn’t drive it out, Jesus said: “Because you have so little faith. Truly I tell you, if you have faith as small as a mustard seed, you can say to this mountain, ‘Move from here to there,’ and it will move. Nothing will be impossible for you.”

That passage always stretches me and my faith, and I’ve not moved any mountains lately.

That tells me that no matter how long we lead, we must continue to pursue our own spiritual growth.

Our faith as leaders is continually stressed, stretched and can grow weary. Do we have the faith to believe for the next miracle we pray for? How can we continue to strengthen our faith?

Our faith is bolstered by:

  • Hearing the Word
  • Experiencing answered prayer
  • The testing of our faith
  • Hearing stories of life change
  • Seeking counsel from those we trust and respect

Mentoring and coaching the strategic side of a leader’s life is necessary and important.

These questions, however, are focused on helping us shepherd the spiritual life of the leaders we are developing.

Shepherding is the care for a person’s overall well-being and spiritual growth.

What elements are required for healthy and productive conversations?

  • An implicit sense of shared trust – the relationship must be one of unquestioned trust.
  • An invitation – This doesn’t mean you need to wait for the person to ask. It means when you open the door, the person needs let you in.
  • An add value response – If you are shepherding a leader, you are not required to have “the answers.” Most personal questions don’t have one set answer, every person’s life is different. It does mean that a response that is encouraging, challenging, re-directing, or has another good question, etc., is needed. The best responses are those that help someone take the next right step.

These questions are not designed to be asked all at one setting. A better approach is asking them and others over a long period of time discerning in the moment which one to ask.

The truth is many of these are lifetime questions to reflect upon.

7 Good Questions to Shepherd Leaders in their Spiritual Life

1) Are you happy with your prayer life?

This question is not designed to instruct someone in any particular structure suggesting things like what to do, what time and how long to pray.

The best questions about a person’s prayer life should not produce guilt and tasks, they should carry a sense of invitation and encouragement that result in relationship.

This question allows for personal assessment. If they say yes, I’m happy with my prayer life. Great. Carry on! Or you might say, that’s so good, tell me about it.

If they are struggling, start by asking what they want their prayer life to look like.

2) What is the last thing you heard God say to you?

Leaders must always be hungry to hear God speak in a personal way, but what do we do in times of seeming silence?

How does God best speak to you? Are you listening? What did He last say? What was your response?

All leaders have dry spells in hearing the voice of God, that should not be a burden carried alone, it needs to be processed with a trusted advisor.

If it’s been a long silence, go back to the last thing heard. No matter how far back. If it’s current, talk about the response.

3) What is your leadership Achilles heel?

Every leader has a particular vulnerability or weakness that under the stress, pressure and demands of leadership we can fall prey to it. What is yours?

You could make a common list, such as power, money, discouragement, moral compass, insecurity, success, anger, pride, and the list goes on. 

Which one is most likely to “take you out?”

The enemy knows which one, so you need to be aware and proactive. The best first step is to bring any “Achilles heel” out in a safe and trusted conversation.

4) Are you able to live in the present?

Most leaders are good about thinking future oriented but struggle to live in the present.

The struggle to live in the moment and be fully present is common to leaders because the nature of our role is to be out in front thinking about where we are going. But the absence of being present weakens our ability to connect, discern, show empathy and at times, even enjoy life.

Some good first step options are, again depending on the person, slowing down, eliminating unimportant non-essentials, learning to listen better, and enjoying a few of the simple things in life.

What prevents you from living in the present?

5) Which is greater for you right now, fruit or joy?

This is one of my favorites and I use it often. Between fruit (results) and joy, which are you experiencing in a greater way right now?

One is always lower the other and that provides a great conversation to move toward a greater balance of the two.

We need both fruit and joy in our leadership lives because fruit without joy is drudgery, and joy without fruit is shallow and hollow. We need both to go the distance in ministry.

6) Do you have a deep sense of abiding peace within you?

Jesus promised these two things. In this world we will have trouble, (John 16:33) but He will bring us peace, so we need not be “troubled.” (John 14:27)

Yet, a surprising number of leaders, perhaps most, will acknowledge a lack of consistent inner peace, and quite often a “low-grade” anxiousness in their gut.

Why does peace elude us? Is it a lack of faith? Trust? Is it a matter of common worry?

If we as leaders are to be present with a non-anxious presence, it must begin with an inner peace that only God can give us.

A good place to start is with this question: What is robbing you of peace?

7) Are you content with your life at a soul level?

The Apostle Paul says in Philippians 4:11, that he has learned to be content. The inference is that contentment is not natural to us and probably doesn’t come easy. What is at the core of your contentment?

What is it that causes us to always desire and seek more, regardless of what we have? What steals soul level contentment?

There is nothing wrong with growth, progress and achievement as long as it is in alignment with God’s purpose for you and your overall spiritual well-being. I hope the last phrase doesn’t sound like Christian jargon, because the opposite is our own independent will and that’s never a good idea.

What does contentment mean to you? What does it consist of? How would you describe your life when you are most consistently content?

I hope these questions help you shepherd leaders, and that they also benefit you.


Have another good question you could add? Please leave it for us in the comment section.