(CNN) -- President Donald Trump flies to Singapore this week for a potentially legacy-making moment when he meets with North Korean leader Kim Jong-un to discuss a nuclear deal. Based on his tweets, it is clear that Trump is eager to demonstrate to the world that he can make this work and accomplish what his predecessors failed to do. Indeed, he appears more interested in achieving a deal with North Korea than he is in maintaining peace with some of our oldest allies.
New York Times columnist Nicholas Kristoff has rightly warned Democrats to avoid blanket cynicism and opposition toward this moment. "Sadly, Democrats in Congress are responding in a quite Trumpian way," he wrote. "They seem more concerned with undermining him than supporting a peace process with North Korea."
When it comes to diplomacy, dialogue, discussion and interaction are always a good thing.
But it is still difficult to predict how any summit will go (especially with two unpredictable leaders such as Trump and Kim). Even when deals are reached they sometimes fall apart. In 1994, President Bill Clinton brought these assets of diplomacy to the table and walked away with the so-called "Agreed Framework" with North Korea to bring an end to certain parts of its nuclear weapons program.
In the end though, Clinton underestimated how determined the North Korean leadership was to build its nuclear arsenal and how much they wanted to use the negotiations as a way to elevate themselves as legitimate players on the international stage. The mechanisms of verification and enforcement did not work. Another agreement that many initially saw as a success was when Franklin D. Roosevelt, Winston Churchill and Joseph Stalin met at Yalta in February 1945. But the agreement looked much worse with the perspective of time.
Most observers may agree that how this Singapore summit could unfold is better than the situation the nation faced last year when the President's tweets threatened to trigger a war.
But there are certain elements of presidential leadership that have been important to success in the past.
Patience: Presidents who have handled these diplomatic moments well understand that they normally take place in fits and starts. It is rare than one meeting leads to the resolution of long-term tensions or produces a final agreement. Successful interactions, like Ronald Reagan's negotiations with Mikhail Gorbachev over a nuclear arms deal, take several tries before they work.
Between 1985 and 1987, Gorbachev and Reagan met three times, with two of the encounters ending in frustration, before the two sides shook hands on a deal. President Trump, and his critics, need to expect that the Singapore summit will likely only be the first of several such meetings if this actually is to work. One of the goals on June 12 should simply be to establish a foundation for another round of discussions.
Frequently, a summit can build momentum for another round of negotiation, even if unexpected. Many in the Reagan administration didn't expect the first meeting with Gorbachev--in Geneva in 1985--to work. Many were skeptical about Gorbachev and thought there were too many areas of difference. Reagan hoped for a breakthrough. The key in Reagan's mind was to end the suspicions both sides had because, as he pointed out, "other questions would follow naturally after this." But when the two men met they had a strong personal rapport. Each summit, even a meeting in 1986 that ended with tension, brought Reagan and Gorbachev closer together and created a path toward success in 1987.
Clear Objectives: Presidents who succeed also have to be incredibly persistent and single-minded in pursuit of their ultimate objective. In his new book about President Jimmy Carter, former advissr Stuart Eizenstat recounts the total determination Carter demonstrated during the Camp David negotiations between the Israelis and the Egyptians. At several moments when it looked like the two leaders were preparing to pack up and leave (literally and symbolically), Carter refused to let this happen, given his clear vision for a peace deal in the region. President Trump, who has a short attention span and tends to show less investment in a goal (he brags that he is willing to walk away from negotiations when they are not working), needs to approach this opportunity in a different fashion. He needs an objective that he feels so strongly about he will invest time and energy in achieving it.
Expertise: Successful presidents bring expertise to their meetings so that they know what they are walking into and what they hope to achieve, even while maintaining a nimble posture. Although there have been many points of comparison between Richard Nixon and Donald Trump, for example, foreign policy expertise should not be one of them. Nixon entered into the discussions with the Soviets and China with immense knowledge of the regional and military issues at stake. Nixon had his secretary of state, Henry Kissinger, by his side (just as Reagan had George Schultz) so that they entered into the room with a strong realistic understanding of the parameters of the conversation. They also understood what a solid, verifiable agreement would look like.
Both Nixon and Reagan also managed to avoid the failures in summits, like when the British signed the Munich Pact that became a symbol of appeasement to Nazi Germany, where the nature and danger of the threat that were faced was underestimated. Presidents need to have the ability to see a bad agreement as well. The risks are extremely high that Kim Jong-Un will attempt to use Trump's eagerness to make a deal as an opportunity to protect his nuclear capacity while gaining international legitimacy. At this point, a basic lack of knowledge about the issues is one of President Trump's greatest weaknesses. The vacancies in his State Department and his diplomatic corps can now come back to bite him.
The President also needs to be cognizant and sensitive to ways that any deal will impact key allies. His verbal tirade against members of the G-7 before leaving doesn't give many of them much confidence that the inter-connected nature of the world will be on his mind.
Confidentiality: Successful presidents have also been willing to keep their cards close to their chest, remaining private about much of their strategy and not putting everything on the table after each encounter. Nixon and Kissinger planned the visit to China in total secrecy so that opponents could not undercut Nixon too soon. This challenge will be harder than ever before in our 24-hour, free-wheeling news cycle. President Trump will have to resist tweeting without thought or without restraint. Reagan limited his comments at the high point of tension with the Soviets, when he and Gorbachev couldn't reach an agreement over the Strategic Defense Initiative, a proposal, which critics derided as Star Wars, that would create a X-ray or laser missile shield around the US (the Soviets insisted on the US dropping this if there were to be a deal). The reason secrecy is so important is that the nature of most negotiations is that they are fragile, tense and always have the potential to fall apart. Making them work requires discipline, focus and the ability to stay quiet.
Can President Trump meet all these challenges? Many doubt that he can and many are rightly skeptical that the Singapore summit can work. Indeed, the President has done a good deal to fuel those doubts, insisting that he didn't have to prepare very much (though also indicating he had boxes of material to go through). And his comments in the months and weeks leading up to the summit have inflamed tensions between us and our traditional allies in a way that undermines confidence in how he will deal with an adversary.
But the fact that the meeting is happening is a good thing and a positive step in world peace. Let's hope that the President is willing to take a look at what some of his predecessors did when they made deals to make the world a safer place.