The featured speaker on Day 1 of the annual VARBusiness 500 event in Manhattan, Ross regaled an audience of partners with insights and anecdotes. Ross has worked with Trump since the 1970s and currently is executive vice president and senior counsel with the real-estate developer.
Sharing numerous tips and war stories, Ross told attendees that the most important factors to any successful business negotiation are developing relationships and being prepared going in.
"Unless you can speak on the same level of the person you're trying to sell, you'll get nowhere," he said. "You have to develop enough of a relationship that the person feels comfortable dealing with you, and the best way to do that is face-to-face."
That may even include feigning a shared interest with your counterpart or presenting an air of legitimacy that makes you seem more authoritative and believable.
"You never tell the full truth when negotiating," he said. "That's what makes it interesting; there's really no right or wrong. You don't have to care, but you have to pretend to care."
Ross also stressed the need for detailed preparation before every phase of a negotiation.
"You have to know what objective you're trying to achieve by the end of every meeting," he said. "Most people go in cold and don't know whether they won or lost because they didn't plan."
In the end, walking away from a negotiation if it isn't meeting your objectives can sometimes be the right thing to do, no matter how vested in it you might be.
"You don't want to get so personally involved that you can't walk away from a deal, and you can save an awful lot of time and effort by killing the right deal," Ross said.
