Christians often pray that God would give them wisdom, and it's right that we should do so. Most often we pray that God would make us wise in a particular decision. Again, perfectly correct. It's just an acknowledgement that God is involved in, and indeed sovereign over, the decision-making process, and that the outcome is in his hands.
Still, I do sometimes feel like we're not really asking for wisdom, but just for the answer. Do we want God to make us wise, or just to have him point us in the right direction for this particular decision? Sometimes wisdom is not much more to Christians than sanctified common sense, sanctified clear-headedness, or even just sanctified 'getting it right'. To put it another way, wisdom is all about the process and the decision; it has no content of its own, it is just the way to get to the right outcome.
In Scripture, wisdom has content. In the Old Testament, wisdom begins with the fear of YHWH (Ps 111:10, Prov 1:7), and works itself out in devotion to his law (Deut 4:6). That is why wisdom is a tree of life, and why such exorbitant promises are attached to the pursuit of wisdom. To be wise in the OT is not really to have a canny sense of what to do in a given situation, or to leap to the right conclusion. To be wise is to know God, to fear God, to study God's ways. Wisdom has a shape. It is about following God, perceiving his work and way and conforming our lives to his revelation. Wisdom is often linked to creation (e.g. Ps 104:24), because the Scriptural authors saw in God's creation his way of working, and sought to follow it.
In the New Testament, the content of wisdom is filled out with a personal name: Jesus. It is Jesus who is the wisdom of God (1 Cor 1:30), and in him that all the treasures of divine wisdom are to be found (Col 2:3). Wisdom is knowing God through Jesus. In Jesus Christ, we see how it is that God works, and so in continuity with the OT, we are encouraged to get on board with God's actions, methods, activities. Wisdom is something that we can learn from Jesus.
The hard part is that this wisdom is particularly the wisdom of Christ crucified. God works through the cross of Christ, through the crucified Jesus. That is why in 1 Corinthians 1 and 2 Paul is insistent that wisdom will not look wise. Wisdom will look foolish, because it hinges on crucifixion. Paul rejects the wisdom of the world, which moves easily from here to there, from where we are to where we want to be, in favour of the wisdom of God, which he reads in the cross of Christ. Far from being sanctified common sense, this is senseless and foolish from a human perspective, but it is nevertheless divine wisdom. It is the way God has gone, which means it is the way things work, which means it is the way we ought to walk.
In practice, I think this means that when we pray for wisdom we should first of all seek the answers to our prayers at the cross of Jesus. In making this decision, which outcome looks cross-shaped - which outcome looks like dying to live? Which outcome looks like the humanly-foolish, divinely-wise action of the cross? I think that will often mean running precisely contrary to common sense. In life, if something is going well, we continue it; the cross may mean giving that thing up to death for eternal gain. In church, we often assume that growth or success should be continued - if we're growing, let's plan for growth! But where is the cross? How do our decisions reflect the Calvary road?
Wisdom is cross shaped, which means it often will cut across what seems good to us. It often will look foolish. But Jesus Christ, and him crucified, has become to us wisdom from God. We should follow him.