The Smart Way to Negotiate Almost Everything

An expert “asker” explains how to score deals on everything from wedding dresses to meals.

By + More

Roxana Popescu, a freelance writer in San Diego, decided to give herself a challenge: She would ask for something every day for a year. That’s interesting for two reasons: First, women tend to avoid asking for things, especially money-related things such as raises. Second, retailers have become more open to negotiation in the wake of the recession. So asking for things is more important than ever.

Popescu documents her efforts on her blog, The Daily Asker, where she’s shared her many successes, including negotiating the price of her wedding dress, her fees for clients, and a phone system at Best Buy. I recently chatted with Popescu about her strategies and advice for people who still find themselves overcome with awkwardness when they try to negotiate. Excerpts:

[In pictures: 10 Ways to Improve Your Finances in 2011.]

When is it easiest to score a deal?

Hotels are often willing to cut rates if they're not at capacity or upgrade you if it's no cost to them, for example if they have empty rooms when you check in. The other biggie is retail, especially small establishments, where you're dealing directly with the owner or manager.

For restaurants, think volume: When you're spending more than the average bill—say, takeout for a birthday party, or reserving a room for a private party—you have a lot of negotiating power. Either ask for a break on the price or see if they'll throw in some extras, like a birthday cake. At chains, now I always ask: Are there any coupons I don't know about? Occasionally, the waiter or counter employee will whip something out.

Any advice on how to increase the odds of success?

Consider what resources these establishments can offer at no cost to them, and in return give them something they value that costs you nothing: loyalty, gratitude, promise of repeat business, mentioning their brand to your 500 Twitter followers.

Is there some ‘secret’ to negotiating? If not, why don’t more people do it?

Believe it or not, there's no secret. But maybe that's the secret. So many people think it takes training, guts, savoir faire. Really, all that's required is the awareness that you can ask and a belief that you should. In my first year of daily asking, I had a 73 percent "yes" rate. As a total beginner. No reason anyone else couldn't hit that same mark.

But here's some tactical advice. Always try to make a genuine personal connection; it's a lot easier to indulge someone you like, isn't it? But remember that some situations require a harsher or bolder approach. And that's okay, too.

[In Pictures: 12 Money Mistakes Almost Everyone Makes]

Do you ever get turned down?

A tag on the blog is called "Ouch." So, yes! But the best thing that can happen to an aspiring asker is to get rejected a lot. Ask for crazy, ridiculous things—and notice that the world didn't stop turning on its axis. Life goes on. No one but you and your mama cares that deeply about what you say or do. That freedom is what helps move past the awkwardness.

Sometimes I still hesitate—but now it's not "What will she think of me?" Rather, "Is this a fair thing to request?" Tell us about this year-long experiment in daily asking.

Can you share some high and low points?

Low: Moments of doubt and sheer exhaustion and repeated failure.

Highs: Asking for my first raise (and getting it!), asking a random New Yorker for travel advice and ending up having dinner with him and a friend, naming someone's kitten, scoring a free airline travel voucher, and watching other people start to ask.

You wrote about negotiating your way into your dad’s ICU hospital room. Do these lessons go beyond money?

The biggest rewards had nothing to do with money. The thousands of dollars I saved or earned by negotiating are worthless compared to those hours I got to spend with him after that surgery. The real message that I'm trying to spread is that asking, if done with an engaged brain and heart, isn't selfish. It's simply a way to express a want or a need and identify corresponding resources or opportunities. Ideally, both parties will improve their position (material, professional, personal, psychological) in that exchange.

Kimberly Palmer is the author of the new book Generation Earn: The Young Professional’s Guide to Spending, Investing, and Giving Back.