The following is an excerpt from Quint Pitt's sermon, Cunning. You can view the full sermon by clicking here:

Do you ever think of Jesus as cunning? When you think of the word cunning, do you think of it as something to which we Christians should aspire? Jesus, for one, is clear eyed about the world we live in and the risks he is asking us to accept when we follow him.

In the first part of Matthew 10, Jesus gives his closest disciples instructions for the short term missions that they will carry out in the towns of Israel. But then in verse 16 Jesus widens his perspective and looks to the future. He’s no longer just addressing the Twelve, he’s talking to you and me and everyone who will follow him and take his mission seriously. He’s preparing us for a mission in a hostile environment, and what he says is real head scratcher. 

"I am sending you out like sheep among wolves. Therefore be as shrewd as snakes and as innocent as doves" (Matthew 10:16).

Addressing this verse, John Eldredge says, “This is the kind of thing you might expect to read in a CIA training manual or maybe whispered by revolutionaries in a secret cell, but this is in red, this is Jesus talking to his little platoon of disciples.” We like that “innocent as doves” part. That sounds nice, it sounds religious, it sounds Sunday Schoolish. But “shrewd as a snake”? That does not compute. When someone says to you, “That guy is such a snake,” do you think to yourself, “Yes, he is a fine Christian”?

You see, everyone else says you must choose between holy and cunning. Jesus says, “I’ll be both.” And moreover, he instructs us to be both.

This begs the question, Why? Why would Jesus instruct us, his followers, to be cunning as a snake? He tells us why in Matthew 10.

"Be on your guard against men; they will hand you over to the local councils and flog you in their synagogues. On my account you will be brought before governors and kings as witnesses to them and to the Gentiles. But when they arrest you, do not worry about what to say or how to say it. At that time you will be given what to say, for it will not be you speaking, but the Spirit of your Father speaking through you. Brother will betray brother to death, and a father his child; children will rebel against their parents and have them put to death. All men will hate you because of me, but he who stands firm to the end will be saved" (Matthew 10:17-22).

In summary, here in Matthew 10 Jesus tells us to be cunning because we operate in an environment of opposition and persecution. That’s obvious to anyone who is paying attention. It’s nothing new. Christians have been operating in these environments since the beginning, and according to Jesus, that’s not going to change.

We see examples of Jesus acting with great cunning in the Gospels. The way he approaches the woman at the well in John 4 leaps to mind. From that encounter I take the idea that cunning is necessary because the direct approach isn’t always the most effective approach.

The conversation Jesus has with a rich young man in Mark 10 reminds me that I must be cunning because human hearts resist rescue. As cunning as Jesus is, there are no guarantees that people will respond positively. Jesus never forces someone to follow him. This life is not a fairy tale, where everyone lives happily ever after, and that is yet another reason for us to live our lives in a balance of cunning and holiness - ”shrewd as snakes and as innocent as doves.”