How leaders can grow in the skill of asking the heart questions

Good leaders are skilled in asking questions that challenge perceptions, reveals attitudes and tests hearts. Lead in truth and clarity.


Daniel 7:13-14

13  “I was watching in the night visions, And behold, One like the Son of Man, Coming with the clouds of heaven! He came to the Ancient of Days, And they brought Him near before Him. 14  Then to Him was given dominion and glory and a kingdom, That all peoples, nations, and languages should serve Him. His dominion is an everlasting dominion, Which shall not pass away, And His kingdom the one Which shall not be destroyed.”

Matthew 16:13-17

13  Now when Jesus came into the district of Caesarea Philippi, he asked his disciples, “Who do people say that the Son of Man is?” 14  And they said, “Some say John the Baptist, others say Elijah, and others Jeremiah or one of the prophets.” 15  He said to them, “But who do you say that I am?” 16  Simon Peter replied, “You are the Christ, the Son of the living God.” 17  And Jesus answered him, “Blessed are you, Simon Bar-Jonah! For flesh and blood has not revealed this to you, but my Father who is in heaven…”

Observation and reflection questions

Context of Matthew 16: Caesarea Philippi was located at the base of Mt Hermon, next to a natural spring that gushed from the mountain – a place of pagan worship and rituals.  In Jesus’ day this city was renowned for animistic pagan worship at the natural spring, Greek worship of Pan, Roman emperor worship of Caesar and even veneration of Philip himself.  

The Greek god Pan – half-man, half-goat, playing the flute. Several images and inscriptions of this god was found in Philippi Caesarea.


Current excavation site of Philippi Caesarea with artist rendition of how it probably looked in the days of Jesus. Note the various pagan temples – especially the temple of Pan at the mouth of the cave – the source of ancient the Jordan River.
  1. It is generally accepted that Jesus’ many references to the “Son of Man” (as in Matthew 16:13) is who Daniel wrote of in his vision (Daniel 7:13-14). With this in mind, what was Jesus asking in his first question?
  2. Picture Jesus walking in this town with religious tourists coming to pay homage to their gods. How do you think Jesus’s two questions were perceived in this environment?
  3. Look at the two questions which Jesus asked his disciples. Compare the two questions in these ways:
    1. Does it ask a general or personal opinion?
    2. Does it cause general reflection or introspection?
    3. Does it discern fact or conviction?
    4. How does the first questions influence the context of the second question?

Personal reflection and application:

Jesus was a master at asking questions that challenged perceptions, revealed attitudes and tested hearts.

  1. Imagine telling Jesus’ parable of the Prodigal Son to a group of men in prison. Write down three progressive questions that will reveal and challenge their perception and relationship with God the Father.


Thank the God for the gift and presence of the Holy Spirit, our Teacher.  Ask the Spirit to teach you to discern your own beliefs, attitudes and motives – and also to lead others in truth and love.

Note: Images sourced from Wikipedia – public domain.

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