Consumer Reports ’ February cover story is “43 Ways to Pay Less for Practically Anything.” One of its tips: shopping online, always negotiate.

That process actually begins the moment you visit a vendor’s site. An algorithm “qualifies” you, just as a salesperson does as you walk into a car dealership. It knows your purchasing history and monitors your real-time behavior, all with an eye to taking you down a path designed to make you click on the “buy now” button.

Sometimes just by waiting, though, you can turn the tables and make the program negotiate against itself.

For example, a few months ago I checked out Greats, a Brooklyn-based company that sells sneaker-style shoes. Immediately it gave me a surprise 10% discount. (Maybe a special enticement for a first-time customer?) I considered a particular model for a while, but exited without making a purchase.

A couple of days later, Greats sent me an email offering a bigger discount on that same item. Back I went back to the site, but I still didn’t bite. A few days after that, Greats offered an even better price. (It was like the street vendor in Casablanca who keeps lowering the price “for special friends of Rick.”)

The moral of that story might seem to be that it pays to wait, but not so fast. That same passive strategy can backfire with other vendors, as I saw last week. I was curious about prices for Udemy’s online platform courses. In the category I searched, most listed in the neighborhood of $100, but almost all were discounted to $11.99. (Psychological anchoring to the max!)

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There was a catch, though. A red alert said the discount was available for only five hours. Indeed, when the time expired, the price jumped up three bucks to $14.99—with a warning that the new price would only be good for 24 hours. After that, it rocketed up to $94.99. Now the moral here would seem to be he or she who hesitates is lost.

Two different companies, with two different negotiation strategies. Each may be smart in its own way. Greats’ focus may be landing new customers. By contrast, Udemy’s priority may be building a reputation for limited-time discounts.

So, what do you do if you don’t know whether you’re dealing with a site that will improve its offers, like Greats’, or one like Udemy’s that holds a grudge? It may seem as if they hold the cards: they know more about you than you know about them, and they make the rules.

But you have leverage. Use it. These sites want your business and you can you go elsewhere.

Instead of rolling the dice, use a proactive strategy, one that will win you bargains where that's possible, but not blow up good deals when the price is firm: Use a site’s chat function to test a vendor's flexibility.

It doesn’t matter whether you’re dealing with a real person or a fully automated bot. The same tactics apply:

  1. Ask for a discount;
  2. Make your request clear (in case you're talking to a simple word-recognition program); and
  3. If you get a no the first time, ask again, cheerfully. 

According to Consumer Reports, negotiating online pays off even better than bargaining in a bricks-and-mortar store. In fact CR’s survey of 56,000 subscribers found that, “Online hagglers outperformed those who negotiated face-to-face getting a sweeter deal 69 vs. 59 percent of the time.”

Here are different chat cards you can play:

  • “When’s the next time this item will go on sale?”
  • “I’m shopping around. If you can take 15 percent off, I’ll buy right now.” 
  • “Can you match the price I saw on XYZ’s site?” (Name the company’s biggest competitor.)

As the saying goes, “If you don’t ask, you don’t get.”

Nevertheless, some people still hesitate to do so, perhaps fearful they might look pushy. (The greater success of online negotiators may be due to the fact it seems less personal.) If you can save some dollars from time to time buying clothes and electronic devices online, why not do it?

Big savings are possible when dealing with subscription services—especially monthly bills for cable, phone, and internet. Securing a discount, of course, means going toe-to-toe with communications giants like Comcast, Verizon, and AT&T.

If you’re shy about doing that yourself, there’s at least one company that will negotiate discounts on your behalf. A San Francisco-based start-up, Trim, has a bot that is said to be polite, yet also firm and persistent. The more it interacts with vendors, the smarter the bot is supposed to get. (Incidentally, I have no connection with the firm and haven’t contacted them, so can’t vouch for performance.)

In any event, negotiating bots are rapidly becoming more sophisticated. And there are already signs that things could get ugly. A flurry of articles has appeared recently with titles like, “Facebook teaches bots how to negotiate. They learn to lie instead” and “Deal or no deal? Training AI bots to negotiate.”

I’ll follow these developments closely and report later this year. 

This article was originally published on LinkedIn Pulse

Professor Mike Wheeler

About the Author

Mike Wheeler is a Professor of Management Practice, Emeritus at Harvard Business School and teaches the Negotiation Mastery course. Professor Wheeler's current research focuses on negotiation dynamics, dispute resolution, ethics, and distance learning. He also co-directs the Negotiation Pedagogy initiative at the inter-university Program on Negotiation. He is the author or co-author of 11 books, and his self-assessment app—Negotiation360—was released early in 2015.