What to do about tasks with a potential negative outcome that cause stress?

If I have stress causing task i want something from someone and might get a 
no, or a the outcome of the task could be negative, I usually get stressed 
and will procrastinate.   I am looking for tips in regards to breaking down 
these stress causing tasks into less worrying action items, or even less 
stressful states of mind. 
I know if you get blocked break it down into smaller steps, but is there a 
mental questionnaire, specifically a process that will allow me to 
eliminate the stress of potential negative outcome tasks.

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