All the "whys" are what I focussed on when I was starting over. It may seem like a lot of torture to think about all these things when on the surface, sketching seems like something you should just do without much thought. But, I had to understand why I was feeling like I wasn't using sketching with intent. I wanted to know how I could use sketching in a way that is helpful in creating successful products.
So I really started to think about how to do this in a repeatable way every day. I needed to put it on paper, and be able to describe what I was doing to others I worked with. I needed to be able to test the idea with others as I tested the practice on projects.
I ended up with a small set of guidelines that were easy enough for me to follow, and it may come off as being obvious, and perhaps stated simplistically, but I'm a simple guy, and I need a clear and easy approach if I'm to have any hope of sticking to it. It's much harder to do these things every day in practice. Believe me, it's easy to get seduced by tools and the details rather than see the bigger picture.
First, I want to talk about the pre-requisites to my guidelines, starting with the basics. What follows afterward is the approach I've laid out for myself that I have been practicing.