Clearly in the Gideon narrative, he lays out fleeces not to try to discern God's will (he knows that God has already revealed it to him) but because he doubts God's word. Judges 6:36-37 make that very clear.
Gideon said to God, "If you will save Israel by my hand as you have promised - look, I will place a wool fleece on the threshing floor. If there is dew only on the fleece and all the ground is dry, then I will know that you will save Israel by my hand, as you said."
Twice he asks God to prove that he will keep his promises. This is not a model of seeking God's will, but an example of how we too often equivocate in response to God's clear will.
What then should we expect in searching for God's will for our lives?
This is a section from the sermon I preached a couple of weeks ago:
What do we do then if the Lord hasn’t spoken clearly on an issue: like our choice of career, church, or marriage partner?
I remember someone preaching this passage when I was a child and talking about how he had ‘laid out a fleece’ when he was uncertain as to whether to propose to his wife: he had said to the Lord that if three people talked about rings that day, then he’d propose to his wife that evening. Three people mentioned rings that day, and, by God's grace they were still happily married decades later.
Are these less than clear decisions the time to lay out a fleece? No! we are nowhere told that in Scripture; it just isn't a biblical model of how we are to make decision. Clearly God can direct our steps in very personal and clear ways; we are never told to wait for him to do that before we make decisions though: we are to pray for wisdom, search for wisdom in his word, and seek the wisdom of other disciples, and then make a decision that we trust will be wise. Indecisiveness is not a sign of humility; it is not a sign of maturity; waiting for God to reveal the future to us before we take any decisions is a sign of a lack of trust in the Sovereign Lord who plans everything to our good. It is sign that we think it is safer to do nothing…
Dave Bish reviews a book here that has the opposite advice for a life well spent: JUST DO SOMETHING!