Great Leadership is about asking Great Questions

by Kylie Butler

[This post originally appeared on Arrow Australia’s blog and has been re-posted with kind permission from the author.]

In my early leadership I believed that people looked to me for the answers, in particular the right answers. I found this quite taxing, each time someone came to me I believed that I needed to have an answer for them, an experience to share, a passage to reflect on, or a leadership skill or insight. I must share something that would be so beneficial and the result would be a changed and transformed life.

But the truth is that didn’t happen, often no change happened at all.

They just ignored my advice. Somebody would come to me and say, “I’m struggling with this, or I don’t know how to do that,” and I felt so much pressure to solve their problem for them. To be smart. To have all the answers.

(And… if I’m honest I enjoyed giving advice. I enjoyed being the smartest person in the room or having the life experience that I could share with others.)

But then nothing… they wouldn’t do anything with my advice or insight. They would do something completely different, and I was left feeling frustrated and confused.

When I went to university and studied Business – I was not taught question asking. I was taught accounting, economics, marketing. I was taught how to review and analyse quarterly reports and performance reviews. When I studied Theology – I was not taught question asking but systematic theology, context, culture, application.  All incredible learning, and I loved it, but not particularly helpful when working with and leading people.

The devaluing of questions can be attributed, at least in part, to our education system in the industrial revolution. During the first and second industrial revolution, the education system at the time was designed to educate and train children to be factory workers, and anything that the worker needed to know about beyond that education would be taught by the manager on the job. The manager was responsible for showing workers what was required on the job and develop them as they made their way up the factory management chain. Rarely did the worker know more than the boss about how the business worked.

This is not the case today. We are living in an age where there is virtually no limit on information, a quick Google search and someone can access the information or answers they require. So, if I’m honest with myself today, if I think I have all the answers to all the important questions – then I am clueless, have no idea of the current world we live in or I’m deluding myself.

One of the most challenging changes a leader needs to make is a paradigm shift.

A world view that we don’t have all the answers, and we may not know what is best or right for the people we lead. Letting go of this advice-giving habit is a hard habit to break but recognising that we don’t have all the answers is a great place to start.

As I look at the life of Jesus, and in particular his communication style, Jesus focused on two things: he told great stories and he asked great questions. Bob Tiede1 researched Jesus questions and found in the four Gospels 339 questions that Jesus asked.
Matthew: Jesus Asked 109 Questions
Mark: Jesus Asked 68 Questions
Luke: Jesus Asked 107 Questions
John: Jesus Asked 55 Questions

Summary:  Jesus asked Questions!

As I look at Jesus’ questions, I can see a few reasons as to why he asks them:

  • To increase engagement
  • To build relationships
  • The questions force people to think
  • Questions created conversations
  • His listeners were more likely to own their own conclusions
  • He sometimes answered questions with questions of his own
  • He sometimes asked warm up questions to get the conversation started

Here are a few examples:

Questions to make a human connection:
When a Samaritan woman came to draw water, Jesus said to her, “Will you give me a drink?” The Samaritan woman said to him, “You are a Jew and I am a Samaritan woman. How can you ask me for a drink?” (For Jews do not associate with Samaritans.)  John 4:7-9

Questions that reminded them of what they already knew:
Some Pharisees came to him to test him. They asked, “Is it lawful for a man to divorce his wife for any and every reason?” “Haven’t you read,” he replied, “that at the beginning the Creator ‘made them male and female,’ and said, ‘For this reason a man will leave his father and mother and be united to his wife, and the two will become one flesh’?  Matthew 19: 3-5

Haven’t you read this passage of Scripture: “‘The stone the builders rejected has become the cornerstone; the Lord has done this, and it is marvellous in our eyes’?” Mark 12:10-11

My favourite question:
“What do you think?” Matthew 18:12

There is incredible power in asking questions rather than providing answers. By asking questions we increase trust, rapport, develop the decision-making muscles, responsibility, and accountability within those we lead.

Michael Bungay Stanier has 3 great questions you can use to get to the heart of the issue when someone comes to you for advice (Quieting the Advice Monster2).

  • What’s on your mind?
  • What was most useful or most valuable for you here?
  • What’s the real challenge here for you?

Why not have a go this week, asking questions before giving advice and see where that takes the conversation.

(If you need some guidance on the sorts of questions you might ask, check out the book from Dr Steve Brown (President of Arrow Leadership North America), Great Questions for Leading Well.)


2 Michael Bungay Stanier, The Advice Trap: Be Humble, Stay Curious & Change the Way You Lead Forever, (Box of Crayons Press, Toronto, 2020).

Kylie Butler

Kylie Butler joined the staff team at Arrow Leadership Australia in 2021, however prior to this she contributed to Arrow as a facilitator for many years.  Kylie has served as CEO, consultant, pastor, leader and coach with many organisations and currently also serves as the Managing Director of Christian Coaching Institute.  Kylie is married to Adam and they have two children, Toby and Lily, and live on the Mornington Peninsula in Victoria, Australia.

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