Matthew 20 covers a parable about workers hired at different hours of the day, Jesus’s third prediction of his death, a request from the mother of James and John, and the healing of two blind men near Jericho. These questions are for small groups, Sunday classes and personal study. You can work through the chapter in order or pick the set that fits your time.
Matthew 20 at a Glance
The chapter opens with the parable of the vineyard owner who hires laborers at dawn, mid-morning, noon, mid-afternoon and the eleventh hour, then pays everyone the same wage. The grumbling of the first workers leads to the closing line about the last being first. Jesus then turns to Jerusalem, warning the Twelve for the third time that he will be betrayed, condemned and raised.
The middle section records the ambitious request of James and John’s mother and Jesus’s teaching that greatness in his kingdom looks like service. The chapter ends at Jericho with two blind men who cry out for mercy, are rebuked by the crowd, and receive their sight.
Observation Questions
Use these questions first, before anyone offers an opinion. Ask the group to point to the exact words in the text, and resist explaining until everyone has had a chance to read closely.
Matthew 20:1-4
1 “For the Kingdom of Heaven is like a man who was the master of a household, who went out early in the morning to hire laborers for his vineyard. 2 When he had agreed with the laborers for a denarius a day, he sent them into his vineyard. 3 He went out about the third hour, and saw others standing idle in the marketplace. 4 He said to them, ‘You also go into the vineyard, and whatever is right I will give you.’ So they went their way.
(WEB)
This short passage sets up the parable and introduces the owner’s repeated trips to the marketplace. Reading it first gives everyone the picture before the surprise of payment arrives. Ask the group to imagine standing in the square at dawn, waiting to be hired.
Matthew 20:12-16
12 Saying, ‘These last have spent one hour, and you have made them equal to us, who have borne the burden of the day and the scorching heat!’ 13 “But he answered one of them, ‘Friend, I am doing you no wrong. Didn’t you agree with me for a denarius? 14 Take that which is yours, and go your way. It is my desire to give to this last just as much as to you. 15 Isn’t it lawful for me to do what I want to with what I own? Or is your eye evil, because I am good?’ 16 So the last will be first, and the first last. For many are called, but few are chosen.”
(WEB)
These verses hold the grumbling, the master’s reply and the chapter’s key saying about the first and the last. Reading them aloud allows the group to hear the tone of the complaint and the calm firmness of the answer. It is the emotional center of the parable.
Matthew 20:22-23
22 But Jesus answered, “You don’t know what you are asking. Are you able to drink the cup that I am about to drink, and be baptized with the baptism that I am baptized with?” They said to him, “We are able.” 23 He said to them, “You will indeed drink my cup, and be baptized with the baptism that I am baptized with, but to sit on my right hand and on my left hand is not mine to give; but it is for whom it has been prepared by my Father.”
(WEB)
Jesus’s question about the cup gives the group a chance to reflect on what discipleship costs. Reading the exchange aloud makes the disciples’ quick reply sound as earnest as it was. Pause here and ask what the cup represents in the wider Gospel story.
Matthew 20:26-28
26 It shall not be so among you, but whoever desires to become great among you shall be your servant. 27 Whoever desires to be first among you shall be your bondservant, 28 even as the Son of Man came not to be served, but to serve, and to give his life as a ransom for many.”
(WEB)
This is the teaching on greatness through service and the summary of Jesus’s own mission. Reading it closes the discussion on power and leadership with the example of Christ. Invite the group to notice the phrase “to serve” as the center of the passage.
Matthew 20:30-34
30 Behold, two blind men sitting by the road, when they heard that Jesus was passing by, cried out, “Lord, have mercy on us, you son of David!” 31 The multitude rebuked them, telling them that they should be quiet, but they cried out even more, “Lord, have mercy on us, you son of David!” 32 Jesus stood still, and called them, and asked, “What do you want me to do for you?” 33 They told him, “Lord, that our eyes may be opened.” 34 Jesus, being moved with compassion, touched their eyes; and immediately their eyes received their sight, and they followed him.
(WEB)
The healing of the two blind men ends the chapter with mercy answering persistent faith. Reading it aloud brings the study to a hopeful close and reminds the group of Jesus’s compassion. Ask who in the room needs to hear that the Lord still stops and listens.
Memory Verse for Matthew 20
Matthew 20:28
Even as the Son of Man came not to be served, but to serve, and to give his life as a ransom for many.”
(WEB)
This verse captures the heart of the chapter by stating that the Son of Man came to serve and to give his life. Memorizing it helps the group remember that greatness in God’s kingdom begins with the example of Christ. Repeat it together at the end of the session and encourage people to say it during the week.
A Closing Prayer for the Group
Father, we thank you that your kingdom is built on grace and not on what we have earned. Forgive us for measuring ourselves against others and for seeking honor when you call us to serve. Teach us to follow the way of your Son, who came not to be served but to give his life for many. Give us the persistence of the blind men, who kept crying out until you heard them, and open our eyes to see where you are at work around us. Help us to live this week with generous hearts and servant hands. Amen.
