Couple your asking clearly with asking confidently. Be confident that your request is reasonable and appropriate to ask that person for it. People who ask confidently are more often successful in receiving what they ask for than those who ask timidly, already sending out signals that “no” will be the answer. Don’t say “You will probably say ‘no'” or any such foolishness. Help the person being asked to say “yes” by asking clearly and confidently.
There’s to be no air of “you ought to give it to me”, arrogance, or meanness in asking confidently. Be confident that even if this person says “no”, you will ask and ask again until success is yours. Be confident that if the answer is “no” that, even though you didn’t receive a “yes” yet, you will keep pursuing what you’ve chosen to pursue. Remember, you are already at “no” before you ask. Receiving a “no” means status quo.
Confidence in asking takes practice. Practice your ask out loud in front of the mirror, with a trusted colleague or friend. Practice makes better and does bring confidence. Practice asking for things you don’t care too much what answer is given. This habit-builder can help you get past the feelings of anxiety we stir up in ourselves and to ask confidently.