One of the things I do for the animal rescue group for which I volunteer is go around to local businesses and ask them to let us hold fundraising or adoption events at their stores.
While I am fairly outgoing, I am not really fond of sales, so it took me a little trial-and-error to find the best approach. Here is what I've learned about how to ask someone to help you:
1. Be brief. I go into a store, go to a register (standing in line if necessary) if there is no customer-service area, and ask to speak with a manager. Once I meet the manager, I can tell him/her who I am, who I represent, and what we would like from their store, all in under 20 seconds. I do not call or email first, because that just enables the manager to stall. Face-to-face, BAM, is the best way to go. And shake hands first.
2. Take materials. As I am doing my initial who-we-are, I hand the manager a rescue group flyer. This gives him something to look at while I am talking and prevents an immediate brush-off. Once I finish up that initial 20-second intro, I give him a picture of one of our previous events, explaining our space requirements. While he's looking at the photo, it buys me a little more time to explain further who we are and what we're asking for. But I don't go on all day. Managers are busy dudes.
3. Be friendly and casual. THIS IS CRUCIAL. If you are nervous and jerky, it stiffs the whole thing. I walk into a store like I don't give a shit if they help us or not (which is true; if they don't, someone else will), and it helps.
4. Explain how helping you will help the store. In my case, I talk about how we bring extra customers into the store, how it's good public relations to help out a charity, and how people always fondly remember the store where they first saw their new pet.
5. Know your shit. If the manager wants some details (How long has your group been around? Who's in charge? How many animals do you adopt out each year? What's your non-profit status?), you'd damn well better have the answers or you're gonna look like a clown.
6. Be polite and follow up. If after the initial pitch I get a brush-off (I'd have to check with my supervisor; we're too busy this time of year to do anything like that; I'd have to clear it through corporate), I ask when I may check back. "If I stop back in a few days/a week/a month, would that be all right?" Because you almost never get an immediate "yes", as it seems NO ONE WANTS TO MAKE A DAMN DECISION, it's important to follow up. That said, if you get an immediate "no way", you need to respect that and not keep pestering. I keep going until I get the "no." Until I get the "no", I'll keep following up. And not by email or phone. IN PERSON. And SMILING.
7. Oh, and for the love of Pete, DRESS NICELY. I always wear either a skirt or a dress, and if I was a guy, I'd damn sure wear a dress shirt and a tie. Show some respect. It matters.
Okay, I think I've about covered it. Dress nicely, be casual, be brief, and follow up. The follow-up part is really important. Last night, I had a store tell me "yes" right off the bat, and that's the FIRST TIME that has ever happened, so remember to follow up!
There ya go. How to beg.