How to ask for a favor cleverly without annoying anyone

Requesting help can be nerve-wracking because, often, you're putting yourself in a position to be turned down. If someone can’t or simply doesn’t want to help, there’s little you can do. However, you can boost your chances by stirring up real emotion. Here are a few methods to try.

Be Direct

Think about the last time someone asked for your help. They probably began with some small talk, then gave you a vague hint that they needed help, meandered for a while, and then finally got to the actual request. Something like this:

Hey, my good friend! How’s everything? All good? Awesome. Got a minute to chat? Cool. So, how's life? Everything’s good on my side too. By the way, are you busy this weekend? If not, I could really use some help. I just signed the lease for a new place. It’s pretty great, you should check it out sometime. Anyway, I need some packing assistance. Anything you could give would be so helpful. I'm not great at packing, and you're so organized. Do you think you can spare some time to lend a hand?

This may seem like a trivial example, but it's not too far from reality. When someone asks for a favor and drags it on endlessly, it gives the person being asked plenty of time to 1) dread the actual request and 2) come up with ways to decline. We tend to beat around the bush for so long because we're scared of rejection. It's that fear that complicates things. Add in some unnecessary pleasantries, and you've got a terribly worded request for help. If you need something, just get to the point.

Be Charismatic and Make Them Feel, Not Think

When you're charismatic, you make others feel great. Everyone loves feeling good, but when you want something, you have to be careful how you use your charm. As we've previously discussed, complimenting someone before asking for a favor can come across as insincere. The compliments often seem empty because it appears you're only offering them to get something in return. It's fine to compliment them afterward, but when it's your opening line, it can feel manipulative. A better approach would be something like this:

Hi [Name],

I'm hoping you could support me by voting in an online contest where I have a chance to win a fantastic prize for my work. It's been a while since we've caught up, and I hope you're doing well. Congratulations on everything you've achieved recently—it's truly impressive! We should definitely catch up over coffee sometime.

Thanks a lot!

Being entertaining really does help. When you're asking for something, making someone smile while you ask often makes all the difference. A friend of mine worked for a television showrunner a while back and found out that this showrunner was filming a new pilot. My friend wanted to be involved and sent this email (personal details removed for privacy):

Hi [RECIPIENT],

This is [SENDER]. I’m sure you remember us being the best of friends during the first season of [TV SHOW]. I was hoping you could let me swing by the set of [YOUR NEW TV SHOW] when filming starts so I can see the process. That way, I’ll remind you just how awesome I am, and maybe your show will get picked up, and you can give me a job! Either way, it’d be great to catch up with you again.

Wishing you a wonderful Martin Luther King Jr. Day!

She initially wrote a version of this letter as a joke, then asked me to help her make it more professional. I told her to keep what she had because it was funny, unpretentious, and kind. Those qualities are rare and should be respected in the entertainment industry. She sent it, and just a few hours later, she got a yes.

A few years ago, I joined a 5k "race" to raise funds for women's cancers. You don't really accomplish anything in this race unless you raise some money, so I sent this message to several people I knew:

I'm about to ask you for money. I signed up for this 5k run/walk with some friends, and apparently, it’s for raising funds to cure women's cancers (sorry to those hoping to cure testicular cancer—not this time). If I raise $100, I’ll get a silly hat that says 'Womentum.' If you want to see me wear that hat, or if you’d like to invest in the preservation of breasts, cervixes, and ovaries, this is the opportunity. Want to get in on it? Click here.

Just a reminder, only you can make me wear this silly hat. (And help cure cancer.)

Though my goal was modest, I raised more than twice what I asked for. People don’t typically donate to a cause because they truly believe in it. Some do, but most don’t. More often, people donate because they like you. I decided to skip the gloomy topic of dying women and the overly optimistic idea that even $1 can make a difference. (Maybe it can, but no one really believes that.) Instead, I made light of something serious, and several people told me they donated because I made them laugh.

So, what have I learned from all of this?

What's the takeaway from these stories? When you're asking for a favor, be direct, brief, charming, and—whenever possible—entertaining. Of course, this is easier said than done, and you won’t always get it perfect. You also can’t win over everyone, so don’t expect to. The next time you need to ask for something, just take a moment to think about how you can make the person smile. If you can do that and get straight to the point, you'll be in a good place.

Photo by Javier Brosch (Shutterstock), iofoto (Shutterstock), Willee Cole (2) (Shutterstock).