The Art of Problem Posing

"What if Not"
I think that the advantage of using the "What if Not" (WIN) strategies is that the teacher can come up with interesting questions. Students are very used to the obvious questions. If the topic being covered is right triangles, then they expect to work around the same type of problems, such as "using the Pythagorean theorem, find the missing lenghts... find the missing angles, find the area..." and they all sound the same, are predictable, and no wonder the students end up being bored. If on the other hand you present the student with a question that seems completely different from what they had heard before you run the risk of having the student engaged into learning.
The way I would use WIN strategy would be when I am coming up with "good" questions when I am lesson planning. A good question has multiple approaches and can lead to rich conversations with many different topics, and at the same time, can serve for the purpose of assessing student progress. I could also use WIN strategies when coming up with a class project. One question might be challenging enough for students to take time, and, why not?, group effort to solve it and then present it to the rest of the class. I think that if I could frame a WIN question with the right real world story behind it, the students might feel motivated to work the problem ahead of them with diligence, enthusiasm, excitement and curiosity as to how the problem is solved.
I think that one weakness of this strategy is that if not thoght thoroughly, when a teacher uses WIN strategies the questions that might arise might not be meaningful or interesting enough. So I think that is why the author even warns the reader on coming up with this questions in a mechanical or automatic way.