The "art" is about phrasing your "ask" in a way that lowers the other person's defenses and puts him or her at ease. The recipient of your request always has three main questions. The more specifically you answer them, the more you increase your chances of getting a favorable response.
1) Why are you contacting me in particular?
Whether you are communicating in person, over the phone, or via a letter, always relate to the person and not the person's job. The typical "I'm an actor and you're a casting director, so I want to meet you" request can feel insulting because it's so generic.
Demonstrate that you know a bit about who the person is. Example: "When Donna Smith (who just directed me in a play) and your client Jason Doe heard I was looking for a theatrical agent known for helping actors move from guest-star to series-regular roles, they both said I had to include you on my list." Another tack: "Not only is 'True Blood' one of my favorite shows, but you were credited with writing my favorite episode of last season: 'Bad to the Bone.' "
2) How much time will this take?
Being vague about the amount of time you want from someone allows that person to envision the worst-case scenario: being trapped for more than an hour with a babbling actor who wants to be hired for something. You can address this concern and put the person at ease by clearly explaining what you want: "I'd love to speak with you for seven minutes at your convenience sometime this month. I have three questions I'd appreciate getting your guidance on."
By phrasing it like that, you are communicating that you know how busy this person is and will respect his or her time, that you know what you want to ask and only seek guidance. Best of all, you're telling the person that the pain will last only a very short time. Requesting exactly seven minutes (or three minutes or 17 minutes) of a person's time is a great way to catch his or her attention and arouse curiosity about you. Plus, it's awkward to reply, "No, I do not have seven minutes anywhere in my schedule to talk to you."
3) Who has to take the next step?
Whenever possible, keep the follow-up ball in your court. If you are making a written request or leaving a voicemail message, state that you will call the person's office for a response on a specific date. Not only does this make it easy for your quarry, but, should he or she wish to decline, an assistant can be delegated to give you the bad news. Giving people an easy and gracious way to opt out of a request demonstrates your respect for them and lowers their defenses.
If it isn't possible for you to make the next move—either you don't have direct contact information or you'd be following up an email with another email, which isn't very effective—then give the person all the information necessary to contact you: "If this is something that appeals to you and if it is something your schedule permits, I can be contacted by email at _________ or by phone at _________. I have enclosed my headshot and résumé to refresh your memory of our meeting."
The people you want to meet are not out of your reach. Be courageous, master the art of the ask, and connect with them.
Kristine Oller is an author, career strategist, and founder of TheActorsLibrary.com, an online source of career guidance for performing artists.