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Negotiation can be challenging. It’s filled with imponderables. It involves emotions and tensions and it makes us uncomfortable.

Seth Freeman, a professor at New York University’s Stern School of Business and Columbia’s School of International and Public Affairs, teaches the skill to UN diplomats, senior executives, small business owners and lawyers. When they share their fears, he takes them to the Latin roots of the word negotiate. The two words “neg otium translate to “not leisure,” which he says in his book 15 Tools to Turn the Tide “means that for at least 2,000 years, people have struggled with negotiations.”

One theme running through his 15 tools is the need to develop many options – for yourself and the other party. He points to a study of excellent negotiators and mediocre negotiators that found the better group, on average, developed many more options – typically five per topic.

To help you in that effort, he recommends a TTT grid, which can reveal promising opportunities you might otherwise miss because it lays everything out visually. The simple chart has four column headings: Topics, targets, tradeoffs between topics and tradeoffs within topics.

Topics covers the issues at stake. What will you discuss and, by extension, what won’t you discuss? That creates an agenda – which can be helpful if you are working with a team – and indicates the time that could be involved.

Targets gets you ready for the competitive side of the negotiations. You need to set a range of what is acceptable for each topic and then also develop a first offer. He stresses the importance of research, which can help you define your best target, an ambitious but realistic goal, and your walkaway, the worst outcome you will accept.

In tradeoffs between topics you rank your priorities between the various issues. A computer parts supplier negotiating a contract with an important new buyer will of course be concerned about price but finds the other party floating the need for a money-back guarantee. If price is the prime priority and guarantee secondary, that gets noted here, so you can understand how to approach tradeoffs in the negotiations. If there are many topics, rank them. Just because one topic is a high priority, he stresses, doesn’t mean you have to give everything else away to satisfy it. Similarly, he warns not to trivialize anything – for example, saying “we don’t care at all about the guarantee” – because your counterparty might figure it’s worthless to you and expect it to be given away.

Tradeoffs within topics allows you to plot creative options for each issue, appealing to the broader interests at stake. He suggests two to four alternatives per topic – but no more, as it can make the grid, and organizing negotiations, unwieldy.

Blend the various items together into a package. He advises that skilled negotiators create a well-cushioned first offer, adding something extra they seek but can later drop. Note your best targets in the first column and add a cushion to at least one topic, allowing you to compromise. If you add cushions to every topic, he points out that may make you seem overly aggressive.

That leads to another tool: The Win Warmly Recipe Card. Studies show that if a negotiator badly “beats” the other party the result can be resentment and a desire to gain revenge from that other party. So you want to leave some money or other gains on the table for that other person.

His recipe is to cushion your first offer; especially cushion your favourite topics; and signal a willingness to be creative.

You need to think through the merits of a large cushion versus a small cushion. Signalling creativity communicates it is possible for both parties to be happy with the result, rather than it being a winner-loser result. He offers this framework: “Let me make an offer and see what you think. I’m not wed to any specific number as long as we come up with an outcome that serves my needs, as well as yours, and I’m confident we can do that.”

Negotiations will undoubtedly still be hard. But maybe easier with those tips.

Quick hits

  • Former U.S. presidential speechwriter and Offline podcast host Jon Favreau found the One-Second App helpful for forcing him to pause before opening an app on his phone, allowing him to consider whether it was a diversion or time waster. A podcast listener suggested putting a big sticky note over the face of the screen with messages like, “You don’t need to see this right away,” or a list of things you want to get done that day. If the note is still sticky at the end of the day it indicates greater success.
  • To make meeting remotely feel less remote, Gayle Hallgren and Judy Thomson of Shepa Learning Company recommend logging into the call early, which opens up the chance to have a conversation with others showing up then.
  • Run toward what makes you uncomfortable suggests sales consultant Colleen Francis. Pay attention to what you avoid doing and recognize it’s probably something you must do.
  • “The very best don’t have to turn it on,” says Farnam Street blog’s Shane Parrish. “It’s always on. They have to turn it off.”

Harvey Schachter is a Kingston-based writer specializing in management issues. He, along with Sheelagh Whittaker, former CEO of both EDS Canada and Cancom, are the authors of When Harvey Didn’t Meet Sheelagh: Emails on Leadership.

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