Haggling Tips For Negotiating Prices When Shopping Online

Marjorie D. can't remember the last time she paid full price for anything. Her secret? The art of negotiation.

On our mission to always save more (especially when discounts aren’t obvious), we wanted to learn how to haggle like Marjorie does. So we tapped into her expertise, alongside insights from corporate trainers and communication experts to unveil proven strategies for successful price negotiations in online shopping. 

From navigating live chats to crafting persuasive messages, these tips will empower you to secure the best deals, even from the comfort of your keyboard.

Meet the negotiation queen: How to think about negotiation

Meet Marjorie D., a savvy shopper who has turned the art of negotiation into an everyday saving strategy. The daughter of working-class parents, Marjorie enjoyed Sunday mornings clipping coupons from the circulars with her mother. "It was fun making a strategy for the week," she says, "and I still love the hunt for a good deal." Marjorie's dad built a successful business buying and selling used vehicles, thinking about negotiations from both sides of the bargaining table, and he applied these strategies everywhere. 

Marjorie says she was sometimes embarrassed by her dad asking for discounts and freebies — he once mortified the family by asking for a free appetizer at a Chinese restaurant — but she learned that you shouldn't be afraid to ask. "You might not get exactly what you want," she says, "but if you don't ask, you won't get anything." 

You might think negotiating prices is limited to yard sales and car lots, but the truth is that you can negotiate the price of anything, including items you buy online. Here’s the best advice we’ve heard from Marjorie and fellow seasoned negotiators to secure the best price.

1. Getting Started – Don't be afraid to talk about money

People fear that if they talk about money, they'll be perceived as tacky or cheap, but Marjorie affirms, "If you don't talk about money from the beginning of the conversation, you're likely to be ripped off." It does take a certain amount of bravery to haggle, but it sure beats the feeling of regret when you've overpaid for something. 

2. How to prepare – Ask yourself how badly you want it

Before negotiating a price, you must ask yourself how badly you want it. You might also ask how much you need it, though haggling over an item you need in a hurry isn't the best place to start a negotiation. However, if you're willing to act quickly on a big-ticket item, there's still an opportunity to haggle a bit on the price. 

3. Pre-haggling – Ask yourself how much you're willing to pay for it

You should ask yourself how much you're willing to pay for the item, but you have to be in a realistic range. To know the product's value, you need to research the product thoroughly. "Understand its features, market price, and the average discount offered during sales," advises C.L. Mike Schmidt, a Santa Fe, New Mexico trial attorney. "This knowledge arms you with the information you need to negotiate effectively."

4. Setting a budget – Be confident, but realistic

Schmidt recommends stating your offer confidently while also remaining realistic. While it's true that you can get great deals on electronics when the next model is introduced, you won't get anywhere with negotiating if you offer $200 for a brand-new iPhone. "A price that is too low might turn off the seller," Schmidt warns. "Make a reasonable offer based on your research and the current market conditions."

5. Remember – Believe that negotiation is possible

If you go into a negotiation thinking, "They're never going to go for this," then they probably won't. Moshe Cohen, Founder and President of The Negotiating Table, Inc., author of several books, including Collywobbles: How to Negotiate When Negotiating Makes You Nervous, and Senior Lecturer at Questrom School of Business, Boston University, says the first step in negotiating prices is to believe that negotiating is possible. 

"Too often, we assume that prices aren't negotiable and don't even try," Cohen says. "We have to take the risk and offer a lower price that the other person will likely reject." Cohen reminds current and future negotiators that "no" is often the start rather than the end of the conversation.

6. Pro-tip – Always start with politeness

The best way to set yourself up for online haggling success is not to be a victim with a sob story about how you want something but can't afford it. Schmidt says that a friendly tone sets a positive atmosphere for the negotiation where nobody is on the defensive. 

"When reaching out to the seller, be polite and respectful," Schmidt reminds, "and remember, good manners go a long way even in the virtual world."

7. Harvard experts say – Know your plan B

If you go in with the mindset that there's only one outcome, you will likely be disappointed. You should know what you want — because it's hard to hit a target you haven't identified — but you should also have a plan B. "Know your best alternative to a negotiated agreement, or 'BATNA'," advises negotiation expert William Ury, co-founder of Harvard University's Program on 

Negotiation and bestselling author of Getting to Yes and six other books on negotiation. 

BATNA was coined by Ury and other Harvard negotiation researchers and is an acronym for "best alternative to a negotiated agreement." "If you can't reach an agreement, what is your Plan B?" Ury asks. "The better your BATNA, the more power you have."

For example, if you're trying to negotiate $400 off a new MacBook, consider alternatives that would make you happy despite not getting exactly what you want. 

8. Haggle like a CEO – Craft your anchor

Shopping negotiations have historically been face-to-face, but online negotiations will involve written or verbal communication. Paul Bramson, CEO at The Paul Bramson Companies, says this allows you to carefully craft your anchor, an important starting point in any negotiation setting. "Because you don't have to worry about the pressure of face-to-face dialogue, you can take your time to create a well-considered anchor that aligns with your goals," Bramson says. 

9. Modern negotiation – Engage in live chats

Shopping online appeals to many people because it doesn't require human interaction, but you'll have to put that aside when negotiating deals online. "Engage in a live chat conversation with a representative," Schmidt suggests. "Express your interest in the product and inquire about any ongoing promotions or discounts. Sometimes, they might offer you a special deal right there."

On sites like eBay, you’re able to message the sellers before bidding or purchasing. According to SimplyCodes marketing specialist and deal-hunting writer Jessica Ho, it’s always worth a try: “Back in college, I really wanted a vintage film camera, and the cheapest listing I could find was for $400, among listings that went all the way up to $800. I simply messaged the seller explaining that I was a student on a tight budget, but I would use the camera to its fullest potential. He kindly dropped it down to $300 and shipped it for free.”

10. The secret – If necessary, pick up the phone

Online chat features often lead you to automated bots not trained (yet!) in back-and-forth negotiating, so you may have to pick up the phone and talk to a live customer service representative. "Pick up the phone and continue the conversation in an actual exchange of dialogue," offers Blaine Little, author, corporate trainer and founder of Momentum Seminars Training & Coaching. "It may not be as convenient, but the clarity will prevent misunderstandings later."

11. The key – Don't think scarcity; think discount 

If you see a catchline next to an item that says "only three left" you might think that scarcity creates more value, but that's not always true when negotiating deals online. Little points out that "only three left" may have been written a month ago and may not be accurate at the moment. 

"Just because something isn't marked as clearance, doesn't mean it's not," Little points out, adding that on at least two occasions, he purchased $500 flat-screen TVs for a fraction of the retail price. "One was a floor model at a store and the last of its kind, the other television was one sent to a YouTube influencer for a demo," Little says. "Most manufacturers do not expect to get those back. I offered each $100, and the response I got back was, SOLD! It never hurts to ask."

12. Insider tip – Consider buying in bulk

Buying in bulk isn't just relevant at Costco. "If you're buying multiple items, negotiate for a bulk discount," Bramson says. "Many sellers are willing to offer lower prices when you buy in larger quantities." 

13. Make it simple – Abandon your cart

If you've ever added items to an online shopping cart and decided not to check out immediately, you've probably received an email asking if you "forgot something." We sometimes do this because we're unsure of the purchase, might want to look for promo codes, or might want to add to the cart before checking out, but this can be a good strategy for negotiating discounts. 

Schmidt suggests adding the items you want to your cart and then intentionally leaving the website without completing the purchase. "Some online retailers track abandoned carts and might send you a discount code to encourage you to complete your purchase," Schmidt says. 

14. The final steps – Check for hidden discounts

If you've already added all of the available coupons you know about, you might think you've reached the best price, but you might be in for a surprise. "Sometimes, there are hidden discounts that only appear during the checkout process," Bramson reminds shoppers. "Go through each checkout step to see if any additional discounts are applied automatically."

Does haggling still exist?

Not only is haggling still viable in the digital age — it’s easier and more powerful than ever with online shopping. The key is to think outside the box, know who’s on the other side of the conversation, and understand how to value items as experts have described in this article. 

Found this article useful? Continue reaping the benefits of expert savings advice on the SimplyCodes helpful content blog, which features more discounting deep dives with coupon experts.

Continue Reading: Sources

• Marjorie D., ceramics artist, general manager at a flower shop, ceramics artist, animal advocate, former loan officer and much more, Missoula, Montana

• C.L. Mike Schmidt, Trial Lawyer at Schmidt & Clark, LLP, Santa Fe, New Mexico

• Moshe Cohen, Founder and President of The Negotiating Table, Inc., author of several books including Collywobbles: How to Negotiate When Negotiating Makes You Nervous and Senior Lecturer at Questrom School of Business, Boston University. 

• William Ury, bestselling author of Getting to Yes and six other books, including POSSIBLE (Harper Business, Feb. 20, 2024). He is co-founder of Harvard University's Program on Negotiation. 

• Jessica Ho, marketing specialist and commerce writer for Dealspotr and SimplyCodes. Researches and reports on shopping trends and consumer behaviors, and coupon data.

• Blaine Little, author, corporate trainer and founder of Momentum Seminars Training & Coaching

Paul Bramson, CEO and Keynote Speaker at The Paul Bramson Companies