Pactum Factum principal Lucia Kanter St. Amour truly enjoys negotiating (in fact, her challenge is to refrain from doing so in situations that do not call for it). But for many people, negotiation causes angst and heartburn. If you don’t believe us, Watch this clip from “The Life of Brian.”

But we can help. Negotiation is like a muscle: the more you exercise it, the stronger you get.  An exercise to get you started is a simple haggle (for a Craigslist item, at the flea market, etc.).  As a first step, take a minute to build some basic rapport with the merchant/seller (even if just to make eye contact, flash a genuine smile, and ask how their day is going. If making an inquiry via email, you can accomplish this with some brief and friendly “small talk.”). Show interest in the item with specific comments (“I appreciate the craftsmanship of this knit scarf. My grandmother used to crochet a similar pattern.”). You can ask a (strategically loaded) open-ended question, such as “How flexible are you on price?” and then observe closely how they answer. At that point, you are well on your way! As a first step (if even this is too daunting) try this: the next time you are checking out of the store, ask simply (with a friendly smile), “Are there any other discounts or offers that apply to my purchase today?” If the answer is no, you are in no worse position than you started and you haven’t lost any face. But you may be surprised at how often the answer is “yes.”