IT SHOULDN’T HURT YOU OR THEM.
Sometimes the difference between success and failure is whether you believe your request could be a “Pain in the Neck (or other area) ” or is something “Needed”. If you believe the help you need is something the other person would benefit by giving it then it’s not only easier to request that help but in some ways necessary but on the other hand if you feel you might be annoying it shows and so does the result. For example I’m looking to go to a trade show that I want others to pay for but if I truly don’t feel that there payment isn’t a good investment on there part then it will be difficult for me to ask for that assistance. If I feel the products I’m selling doesn’t benefit the customer then the sell will fall flat. Belief in what you are doing is better for others and then it will be better for you as well.