Why did Jesus ask the disciples how many loaves they have after they told him they would not have enough?
Jesus wanted them to see not what they lacked, but what they had. He stressed the positive, while the disciples so easily fell into negativity (Matthew 15:33). His question showed that they were even better provided for than on the previous occasion (Matthew 14:17), with seven loaves instead of five, and a few small fish instead of two, and fewer people to feed (Matthew 15:38).
Jesus did not want the disciples to be preoccupied with what they lacked and so he asked them what they had. He focused on the positive, while the disciples so easily fell into negativity (Matthew 15:33). By asking this, he now highlighted that they were now on this occasion even better provided for than on the previous occasion (Matthew 14:17): There were seven loaves instead of five, and a few small fish instead of two. Moreover, there were now also fewer people to feed (see Matthew 15:38).1
34 And Jesus said to them, “How many loaves do you have?” They said, “Seven, and a few small fish.”