Each week, the “Can He Do That?” podcast explores critical questions about what today’s news means for our nation and its highest office. Listen here.

When President Trump announced his plan to sit down for an in-person talk with North Korea's Kim Jong Un, there was one person who was particularly surprised by the move: Christopher R. Hill, a former U.S. diplomat who led negotiations with North Korea in the mid-2000s.

His first reaction to the news?

“Well, great skepticism, obviously,” Hill said this week. “But on the other hand, it's better than him saying, 'I have a new idea for bombing North Korea.'”

On this week's episode of “Can He Do That,” we're talking about Trump's plans to negotiate with North Korea — and how those plans will be shaped by the recent shake-up at the top of the State Department. Can the president successfully navigate this incredibly delicate diplomatic relationship?

Hill, the assistant secretary of state for East Asian and Pacific affairs under President George W. Bush, says he believes that it could be a mistake for Trump to sit down with Kim before sending in diplomats and appointees to lay the initial groundwork.

“Once you have had the president go in there and not succeed, I'm not sure who else you turn to,” Hill says on the podcast. “So what I think would be a better way to proceed is to begin to have a series of discussions with the North Koreans on what they are prepared to do to tease out what they have apparently said about wanting to give up the nuclear program in return for some kind of security. What do they mean there? Is there something new there? I would think there would be.”

Karen DeYoung, associate editor and senior national security correspondent for The Post, agreed that Trump's strategy on this is unconventional and demonstrates an “enormous amount of confidence in his own ability.” Previous presidents have taken a much more cautious and methodical approach to negotiations with North Korea — but in some ways, Trump's brisk approach might be seen as a tactical opportunity.

“Other people have argued that, well, yes, this has gone on for many, many, many years with North Korea, and it's basically gotten nowhere,” DeYoung says. “And so why not? Why not just go for broke and sit down and have the two leaders sit down, and maybe they will make some kind of big deal?”

Each week, “Can He Do That?” explores critical questions about what today’s news means for our nation and its highest office. Subscribe on Apple Podcasts, Stitcher or wherever you get your podcasts.

Departures that made headlines during Trump’s administration

Kevin McAleenan | President Trump said on Oct. 11, 2019 that he was replacing Kevin McAleenan, the acting secretary of the Department of Homeland Security, after a tenure where McAleenan lowered border crossings but clashed with other senior immigration officials and struggled to earn the trust of the president. Read the story (Jabin Botsford/The Washington Post)