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How to Be Clever, and Not Annoying, When Asking for a Favor Asking for a favor can be scary because, in many cases, you're asking to be rejected. If someone can't (or doesn't want to) help you, there isn't much you can do about it. You can improve your chances by inspiring genuine emotion. Here are a few ways to do that.

Get to the Point

How to Be Clever, and Not Annoying, When Asking for a Favor Think about the last time someone asked a favor of you. Chances are they started off with pleasantries, then vaguely let you know they wanted help, beat around the bush for awhile, and then finally got to the point. You know, kind of like this:

Hey good friend of mine. How are you? Good, good. You got a minute? Cool. Yeah, so how's life? Mine's pretty good, too. By the way, are you busy this weekend? Maybe? Well, if you're not I could use some help. I just signed a lease for a new apartment. It's really nice. You should come see it some time. You'd like it. Basically, I need help packing. Any time you could give would be great. I'm just so bad at packing, and you're so organized and together. Do you have any time to help me?

This is a silly example, but not too far off from some realities. When someone asks for a favor and they draw it out endlessly, it just gives the person being asked so much time to 1) worry about what the question is going to be and 2) figure out how to say no. We tend to waffle around the point for so long because we're afraid of getting rejected. It's that fear that does us in. Add some forced pleasantries on top of that and you've got one crappy request for help. When you want something, you need to get to the point.

Be Charming and Get Them to Feel, Not Think

How to Be Clever, and Not Annoying, When Asking for a Favor When you're charming, you make another person feel good. Everyone likes to feel good, but when you want something you have to be very careful about how you employ your allure. As we've previously noted, complimenting someone before you ask for a favor makes you seem untrustworthy. The compliments fall flat because they sound, to the recipient, like you're only giving them because you want something. It's fine to compliment someone afterwards, but when it's the first thing out of your mouth it is ruined by asking for a favor. It's better to try something like this:

Hi Person,

I'm hoping you could vote for me in an online contest where I can win a big prize for my work. I haven't seen you in years. I hope you're doing well. Congratulations on all you've been doing. It's really amazing! We should grab coffee sometime.

Thanks!
Another Person

It also helps to be entertaining. When you want something, if you can make a person smile while you're asking you've probably won them over. A friend of mine worked for a television showrunner a few years back and heard this showrunner was filming a new pilot. My friend wanted to get involved and sent the following email (details redacted for privacy purposes):

Hi [RECIPIENT],

This is [SENDER]. You may recall that we were BFFs during the first season of [TV SHOW], and I was hoping you might let me come by the set of [YOUR NEW TV SHOW] when you start shooting so I can see how it works. That way I can remind you of how awesome I am, and then hopefully your show will get picked up and you can give me a job. Regardless, it'd be nice to see you again.

Happy Martin Luther King Jr. Day!

She'd drafted a similar version of this letter as a joke, then asked me to help her write a more professional version. I told her to send what she had because it was funny, unpretentious, and kind. To someone in the entertainment industry, those ought to be rare and respected qualities. She sent it and received a yes a few hours later.

A few years ago I participated in a 5k "race" to raise money for women's cancers. Your participation in this race is mostly pointless if you don't raise some money, and so I sent this message to a bunch of people I know:

I'm about to ask you for money. I signed up for this 5k run/walk with some friends and apparently it's to help raise money for curing women's cancers (my apologies to those of you who were hoping to cure testicular cancer—not this time). If I raise $100, I get a stupid hat that says "Womentum." If you'd like to see me in a hat that says "Womentum" and/or you'd like to invest your money in the preservation of breasts, cervixes and ovaries, this is a spectacular opportunity. How do you get in on the ground floor? Click here.

Remember, only you have the power to make me wear a stupid hat. (And cure cancer.)

While my goal was fairly modest, I raised more than twice what I asked for. People often don't donate money to a good cause because they believe in it. Some will, but most won't. More people will donate to a cause because they like you. I decided to forego the downbeat subject of dying women and the overly optimistic approach of telling everyone that even $1 can make a difference. (Maybe it can, but nobody really believes that.) I opted to be silly about something that's fairly serious, and several people emailed me to say they were donating because I made them laugh.

So, What Did I Just Learn From All of This?

How to Be Clever, and Not Annoying, When Asking for a Favor What's the moral of these stories? When you ask for a favor you should be direct, succinct, charming, and—whenever possible—entertaining. Obviously this is easier said than done and you won't always get it right. You also can't win over everybody, so don't expect that you will. Next time you need to ask someone for a favor, just remember to set aside some time beforehand and think of a way you can make them smile. If you can do that and get right to the point, you'll be in good shape.