US-based scholar Bob Carlin served as a senior policy advisor at the Korean Peninsula Energy Development Organisation (KEDO) from 2002-2006.
And the North Korea expert, who has made more than 30 trips to North Korea, told Pyongyang watchdog 38 North exactly how Mr Trump should tackle the talks.
Mr Carlin advised that “seizing control” of the agenda, is a bad idea.
He said: “The North Koreans know we won’t negotiate simply on the basis of ‘their’ agenda, and we should know the same about them.
“It never hurts to be the first one to put a piece of paper on the table, and since the North Koreans are frequently in reaction mode, that’s often what the US is able to do.
“Win-win is a loathsome term as far as I am concerned, because it has become a hollow slogan.
“Nevertheless, the essence of the term is critical and is something the North Koreans understand very well.
“They can’t get everything they want, we can’t get everything we want, but we can both get something we each consider important. Otherwise, there is no agreement.
“In every negotiation I was at with the North Koreans over twelve years, they bargained hard – as did we – but they never tried to humiliate or disgrace us. When they went home they claimed victory. So did we.
“We never failed to complain to the North if they did something at the negotiations that was objectionable.
“At the same time, we have to be prepared to sit and take it when we go over the line with them.
“Fortunately, these episodes become few and far between as the two sides smooth off the rough edges in face-to-face encounters.
“Rarely do the North Koreans pound the table. More often, when we raise a point they find objectionable, they may quietly take off their glasses, close their notebooks gently, and lay their pens to the side.
“High-level meetings with the North, in my experience, have not been a zero-sum game. The last thing we should want is to force them into that mould.”
US Defence Secretary Jim Mattis and new CIA chief Gina Haspel will be tasked with preparing Mr Trump for his meeting with North Korean leader Kim Jong-un.
The talks, which are already under intense scrutiny, come as the Trump administration shakes up the White House team.
Mr Trump fired Secretary of State Rex Tillerson today after a series of public rifts over policy on North Korea, Russia and Iran, replacing his chief diplomat with loyalist CIA Director Mike Pompeo.
Senior White House officials said Mr Trump wanted his new team in place before any summit with Kim, who invited the US President to meet by May after months of escalating tensions over North Korea’s nuclear and missile programs.