From a CT interview with NT Wright,

The Dick Staub Interview: Tom Wright's Theology for Everyone - Christianity Today Magazine:

"We hear the phrase, 'engaging the culture' almost ad nauseam today. What you think it means truly to engage the culture, and what Jesus teaches us about the incarnation, being transforming. What does it mean from Jesus' life and teaching to engage the culture?

I'm not sure I would start with Jesus because Jesus was doing something unique and unrepeatable and he was not just being a model of how we should be good Christians. Jesus is not the first Christian in that sense. Jesus is the one who makes possible a way of life which we loosely call Christianity. And his achievement in his death and resurrection was thoroughly enculturated. It meant what it meant within the culture which God had prepared. Paul says, 'When the time had fully come.' God prepared that culture so that Jesus, by being thoroughly within the culture and doing what he had to do, would make the sense God wanted him to make.

We can then see Paul and the others going out and engaging their culture. Look at the Areopagus address in Acts 17. Paul begins by saying, 'You've got an altar to the unknown god, well I'm going to tell you about this unknown god.' Then he says, 'You also have all these temples made with hands, but I'm going to tell you that the true God does not live in temples made with hands, but I'm going to tell you that the true God does not live in temples made with hands. He's not like that at all." So he's saying yes to this and no to that, and then he negotiates his way through stoicism and epicureanism and so on, engaging the culture all the way, quoting their own poets but showing that they might mean something different. Now, that's wonderful cultural engagement and it's not a matter of saying no to everything, it's not a matter of saying yes to everything, it's a matter of Christian discernment in seeing what is good, seeing what can be redeemed, what can be refreshed."