Here are some examples, then I'll ask my questions:

I took this photo of my friend next to her window. I LOVE this portrait lighting and want to learn how to recreate this with a speedlight and light modifier.
Here is what I've been getting:
So I put my umbrella on it to diffuse the light and all it does is this:

I wanted more light to be noticeable on his left side of his face, but it just spread it everywhere.
How do I do this? Do I need a softbox for more soft directional light? I am using a satin white umbrella. I shot through it and bounce and still don't get directional light, like the window gave me in my first photo of my friend.