President Trump certainly has a flair for the dramatic.The announcement Thursday night that the president of the United States had accepted an invitation to meet with North Korean dictator Kim Jong Un shocked the world.That is the kind of phrase that is overused — in politics and sports, in particular — but it's appropriate in this case."This is quite extraordinary," former U.S. Ambassador Chris Hill told NPR's Mary Louise Kelly on All Things Considered on Thursday night. Hill represented the U.S. in multilateral talks with North Korea during the George W. Bush administration.Extraordinary because no other sitting U.S. presidents has met with a North Korean leader. (Jimmy Carter met with then-North Korean leader Kim Il Sung in 1994 as a former president, and former President Bill Clinton traveled to North Korea and met with Kim Jong Il in 2009 to negotiate the release of two journalists.)Extraordinary because the rhetoric between the countries has been heated in recent months with Trump referring to Kim as "Little Rocket Man" and a "madman," and Kim referring to Trump as a "lunatic" and "loser."Extraordinary because few thought this realistically could happen. Trump has said in the past that he would be open to meeting with Kim, but on Tuesday when asked about the possibility, he was noncommittal. "We're going to see what happens," he said.The surprise nature of the announcement gave the impression of an ad hoc gambit rather than a careful, well-thought-out approach to dealing with an unpredictable nuclear regime.In diplomacy, it comes with incredible risk to subject a principal to a one-on-one meeting where results aren't guaranteed — or at least close. Typically, spade work is done by lower-level experts for months, if not years.Trump is banking on the power of his personality for a breakthrough. But some recent domestic examples provide little evidence Trump will deal with this particularly thorny issue masterfully.After Trump's televised meetings on immigration and guns, participants were left confused. Instead of command performances, there was disorganization and a lack of policy depth.What's more, the Trump administration's stance on North Korea has been something of a whiplash. Washington, with Trump's backing, has pushed for ramping up sanctions against Pyongyang. And the White House reportedly scoffed at the State Department's special envoy who tried to pursue direct talks late last year."He's such a dreamer," one White House official told Reuters sarcasticallyof State's point man on North Korea, Joseph Yun.Seemingly out of frustration with a lack of effort at pursuing direct diplomacy and a peaceful solution, Yun retired — just last week.When it comes to an issue as dangerous and delicate as North Korea, this isn't how it's normally done. At the same time, Trump's theory of everything is that the way it has always been done hasn't worked, so let's try something else.Progress with cautionThat high-risk, high-reward approach has its skeptics, but not everyone is dismissing it out of hand."We were quickly heading down the road to a possible military confrontation with the North Koreans and a major step towards diplomacy is a most welcome turn of events," Suzanne DiMaggio, senior fellow at the think tank New America, said on NPR's Morning Edition on Friday.Hill, the former U.S. negotiator on North Korea, said Trump's out-of-the-box stance may very well have been what spurred this."Frankly, he may be right about some of this, because it was pretty clear that the U.S. was kind of going relentlessly on this issue," Hill said on All Things Considered. "And he's such a — how to put it — different kind of president that — he seemed to be prepared to talk about things that other presidents have not been prepared to talk about."For example, in Washington the last few weeks, there's been a discussion about the so-called bloody nose and the idea that somehow we could launch some kind of strike against the North Koreans," he added. "So it could be that this kind of attitude unconstrained by what anyone in the past has done kind of gave the North Koreans pause."DiMaggio and others said preparation and expectations-setting are going to prove important. In particular, the president should stop raising the bar for the possibility that the North will give up its nuclear program entirely, like the White House and the president did Thursday."We look forward to the denuclearization of North Korea," White House press secretary Sarah Huckabee Sanders said in a statement. "In the meantime, all sanctions and maximum pressure must remain."The president then tweeted that Kim "talked about denuclearization ... not just a freeze.""We need to go into the mindset that this is going to be a long, arduous process," DiMaggio said. "The North Koreans are not going to give up their nuclear program anytime soon. They may well never give it up. ... We need to really get in place the priorities that we want to achieve in the near term."But the expectations horse may have already left the barn. Here was Colorado Republican Sen. Cory Gardner on NPR's Morning Edition: "If the president of the United States meets with Kim Jong Un and does not walk away with what should be those concrete steps towards denuclearization, then I don't see how it's any closer to the kind of peace on the peninsula that we have been seeking."Hill cautioned against that mindset, saying there need to be other attainable goals on the table. "It's important to get down all the steps with the last one being complete denuclearization," he said."I don't think we're going to get an absolute goal of denuclearization," Bill Richardson, a Democrat and former ambassador to the United Nations who has been to North Korea eight times, said on CNN on Friday. "I think the president needs to temper that.""Risks need to be mitigated by very good staff work"Preparation is key, experts agree, but the staffing situation in the White House and at the State Department makes observers nervous."What's important," Hill said, "is the U.S. has some clear understanding of what goes forward, because a presidential meeting is kind of coin of the realm, and the idea that we are just going to have a pause in their testing without really concrete understandings of what goes forward — that's risky, and those risks need to be mitigated by very good staff work."When it comes to that staff work, there are some danger signs. Diplomatic experts have been sidelined in this administration. As NPR diplomatic correspondent Michele Kelemen points out, there is a thin bench at the State Department currently when it comes to dealing with North Korea — not only did Yun retire, someone who joined the foreign service in 1985, but there is also no assistant secretary of state for East Asia (she's currently going through her confirmation process). Trump still hasn't nominated an ambassador to South Korea.A career diplomat is currently serving in that role, which can be a good thing, but all of it points to unsteadiness and inconsistency at the staff level, and in talks with a rogue regime, one false move can have massive ripple effects and unintended consequences.What's more, when the announcement came down, it was the deputy secretary of state at the White House, not Secretary of State Rex Tillerson. He is currently in Africa. He said this was not a "surprise," but he also signaled that Trump made the decision on his own.This was "a decision the President took himself," Tillerson said, per CNN, in Djibouti, a day after Tillerson questioned "whether conditions are right" for negotiations."We're a long way from negotiations," Tillerson said in Ethiopia on Thursday. "We just need to be very clear-eyed and realistic about it. I don't know yet, until we are able to meet ourselves face to face with representatives of North Korea, whether the conditions are right to even begin thinking about negotiations."On Friday, though, Tillerson was put in the position of trying to walk a very fine line between the words "negotiations" and "talks.""With respect to talks with North Korea versus negotiations," he said, "and I think this seems to be something that people continue to struggle with the difference — my comments have been that the conditions are not right for negotiations." Can Trump stick to the script? Either way, talks or negotiations with North Korea are high stakes, especially when the president is involved. And this president, in particular, has had trouble sticking to the script."His primary problem is sticking to talking points and really laying the kind of groundwork that has to be laid for the kind of serious negotiations that are going to take place," former Obama Defense Secretary and CIA Director Leon Panetta told CNN."It's risky," Richardson said. "We've got to be properly prepared, and we cannot underestimate Kim Jong Un. He's evolving into a strategic thinker, into a man with an endgame."To that point, congressional Republicans are sharpening their sabers."I do believe that North Korea now believes President Trump will use military force if he has to," South Carolina Republican Sen. Lindsey Graham said in a statement. "A word of warning to North Korean President Kim Jong Un — the worst possible thing you can do is meet with President Trump in person and try to play him. If you do that, it will be the end of you — and your regime."Still, while Trump's agreeing to a meeting surprised almost everyone and didn't relieve skepticism, experts welcomed the news."This is a positive step," Panetta said. "The world is breathing a sigh of relief as a result of having these negotiations, even having this kind of meeting."But they warned about something else: "One of the first priorities is going to have to be how to soundproof this process from President Trump's tweets and rants," DiMaggio said, "otherwise we are going to be in for a rocky road ahead."Or, as Richardson put it: "I think this is big stakes, a big gamble, but I'm supporting the president's effort to do it. Just be careful and don't tweet. Don't tweet. Just stay low." Copyright 2018 NPR. To see more, visit http://www.npr.org/.