To Become A Confident Negotiator, Start By Asking For Things

If negotiation makes you think of haggling, bargaining or wheeling and dealing, you’re picturing transactional negotiation. These are one-time exchanges, like buying a car or selling a home. In transactional deal making where you don’t need to maintain a relationship, you can be as aggressive as you want since you don’t need to be friends at the end. For example, I moved recently, and I negotiated hard with three different moving companies to get the best price and package. The company I eventually hired lowered their price by more than 50% from their original quote.

Negotiating in situations where you do need to maintain your relationship at the end (any sort of career or workplace negotiation, or certain interactions with family and friends) is more nuanced and ideally takes place after careful planning. But getting more comfortable with transactional negotiation can help make asking a habit.

If you want to become a more confident negotiator, start by putting yourself in more transactional situations where you can get used to asking for things.

Here are six easy opportunities to practice transactional negotiation:

  1. Get the heels or soles replaced on your favorite shoes. Shoe cobblers are often small shops that will negotiate with you on price.

  2. Ask for a discount on something that’s not on sale at a department store.

  3. If you’re a loyal customer at your dry cleaner, ask for a better price on the next item you bring in.

  4. Ask for an upgrade to your rental car, airline seat or hotel room on your next trip.

  5. Joining a gym? Ask to have your initiation fee waived.

  6. Call your cable, internet or cell phone provider to ask for a discount.

Try asking for something bigger or better than what your gut initially tells you to do. Women often set less aggressive goals than men, so view this as an exercise in correcting the impulse to set a “realistic” — lower — bar. If the cobbler says it’s $50 to replace your heels, rather than counter offering $40, try countering with $25.

It’s ok if you get turned down. But you might be surprised at what works. The point is to build your comfort and confidence levels so that asking feels normal. So long as you are respectful, the worst that can happen is you get told ‘no.’

Use direct, declarative language rather than beating around the bush: “I would like a discount,” rather than “Do you have any specials going on?” Why ask a yes or no question that makes it easy for them to say no? In fact, most people want to be helpful and feel a strong social pressure to say yes to requests. If this feels awkward, try practicing your ask out loud a few times.

If you get turned down the first time, it’s ok to ask again: “It’s too bad you don’t have any discounts available, because otherwise I can’t buy anything today. Are you sure you can’t help me out?” It may sound counterintuitive, but someone who’s said no the first time may actually feel guilty about it and therefore be more likely to agree the second time around.


Even if you don’t get everything you ask for, I’m betting your negotiation confidence level will get a big boost by the time you’ve completed these tasks.

This post originally appeared in Women@Forbes, where Alexandra Dickinson is a contributor. She writes about how to use a negotiation mindset to achieve your goals.

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Alexandra Dickinson

Alexandra Dickinson is the CEO and founder of Ask For It, a boutique consulting company working to close the gender wage gap by effecting change at both the institutional and individual level. We work with companies, schools, organizations and individuals through a combination of trainings, workshops and consulting. Our goal is for women and men to be paid based on their talents and skills, regardless of gender, and for our company to have been an important part of that change.