Practice stuttering - both of you - so that a stutter is not seen as "bad" nor "good"...just: stuttered. Then, practice pulling out of a stutter.
My students actually like stuttering "real hard" ...and then contrasting with a smooth target.
Explain that you're giving him a toolbox of techniques to use for fluent speech OR to pull out of stuttered speech.
Each session - practice 1 of the techniques you listed ...and then apply the technique into a conversation situation. (game - or practicing conversation situations he finds difficult like phone or message delivery or classroom explanation.) Have HIM tell you how he did ...and how he could make his speech more fluent. And/or how he will react when he does stutter in those situations. YOU stutter - and have him give you advice.
Go online together to find info about public figures who deal with stuttering.
I know that we can work on getting fluent speech by increasing the complexity of the utterance. Maybe it'd help him too, though, to remove a bit of the stigma he's feeling (for whatever reason).
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