In my opinion, the strengths of this portrait are tonalities and lighting.
The highlights, might need just a bit more work, I would print them a little lighter to create a tension with the shadows and midtones to support the mood you are trying to convey.
I agree that the subject is a tad stiff, or maybe uncomfortable.
Or it could be that you were a bit uncomfortable thus not being able to capture yourself and him in the picture.
You probably need to get acquainted in shooting portraits with LF, which can be a blessing but it require total confidence with the camera at the point you forget you are using it, so that you can concentrate on the subject and yourself.
I love the background and its tonalities, but as it has been mentioned, there is too much on top of the head
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