From the Idealist blog:
A lot of us have problems asking for things flat out. And, depending on your personality, cultural background, and communication style, it could be really difficult for you to ask for things directly.
If you want to improve your approach to asking, writer and communications expert Sarah Kathleen Peck offers advice, including:
Ask at the right time: understand how (and when) people make decisions.
If you’re asking for something complicated and difficult, ask while the asking is good. People grow weary of making decisions by the end of the day—we usually make better choices (or are willing to make choices at all) in the morning, or whenever else we’re fresh (see more on decision fatigue in Psychology Today). In the evening, you’re more likely to get a “no” as a response if the person you’re asking is tired and worn out from a long day.
Read more tips on how to prepare a good "ask" here.