ARI SHAPIRO, HOST:

If you make a list of the most harrowing places in the world, you might begin with Iraq. Next, we could add North Korea, and then maybe throw in the Balkans in the 1990s. And that's basically the resume of Ambassador Christopher Hill. He has a new memoir out called "Outpost: Life On The Frontlines Of American Diplomacy." Welcome to the program.

CHRISTOPHER HILL: Thank you very much.

SHAPIRO: I want to discuss the book and the arc of your career, but I have to ask, as a former ambassador to Iraq early in the Obama administration, whether you look at what is happening in Iraq and feel a sense of futility?

HILL: Well, certainly, when you look at Iraq today, you feel a sense that you had when you were living there that this is a huge problem. It didn't just start yesterday, and it certainly didn't just start with the election of Prime Minister Nouri al-Maliki, difficult person that he is.

SHAPIRO: He's the - I should just clarify, he's the Iraqi leader whose sectarian policies of ruling sort of were believed to led, in part, to the rise of ISIS.

HILL: Yes. I mean, he was a Shia leader. And as a Shia leader, he had a sort of Shia view of things. The problem is it was not at all clear then and it's not at all clear now that the Sunni-Arab world is prepared to accept a Shia-led Iraq. And I think that continues to be the sort of fundamental problem whether there's a prime minister named Maliki or someone else.

SHAPIRO: You talk in the book about these marathon negotiating sessions with, at times, very unsavory people. And I get the sense that you feel that to be lacking in current American policy.

HILL: I think, to some extent, it has been because there's this notion that to deal with America is to deal with this kind of pristine place. And therefore, we're not going to talk to people who, in some respects, don't share our values. And when you don't talk to someone who doesn't share our values, you're probably not going to be talking to the people who really are responsible for the mess.

SHAPIRO: Well, is that change because America considers it distasteful or is it a change of priorities from the top that this won't be how we approach the problems of the present day?

HILL: I think, to some extent, there was a hope that very distasteful Bashar al-Assad would go quickly in the way the others went quickly in the Arab Spring. The trouble is the problems of Syria are kind of made of sterner stuff. And when you talk to someone like that, you need to have a clear understanding of what you're trying to achieve. Negotiation is always easier when you have a relationship with someone. But it's pretty hard to have a relationship with some of these people. So you have to be, to some extent, transactional. You have to approach them with a sense that OK, we can get to point X through these talks. And then when you don't get to point X or when something goes awry, and it often does, then people say, well, why are we talking to these terrible people. So it's a very tough proposition.

SHAPIRO: You write that from 1990 to 1992, the State Department opened 20 new embassies around the world in places with almost no infrastructure. And it's hard to read that without wondering whether the influence of U.S. diplomats has waned and maybe even been eclipsed by the military. What do you think?

HILL: Well, certainly we were everywhere. And you're right. We didn't have any military component. I mean, you couldn't spread your military all that way. So we became the face of the United States.

SHAPIRO: And how would you compare that sort of flood-the-zone moment of American diplomacy to the present day?

HILL: Today, think it's much more focused on very, very tough issues, but tough issues involving war and peace. And when you have these kind of war and peace moments, where you lead is with your military. And again, we have the world's finest military. But to lead with a military and not with a civilian component, I think, has downstream consequences.

SHAPIRO: At so many moments in your career, you have gone to tackle these seemingly unsolvable problems. And in some cases, like the former Yugoslavia, you solve them. And in other cases like North Korea and Iraq, the problems remained after you left. And I wonder how you go in to these challenges knowing that the odds of success are so very slim.

HILL: Well, I think it works for anything in life. You go in and you throw yourself into it. And you say, I'm going to do the best I can. And if at the end of the game you lose, it's not because you didn't try. But I'd like to also mention the fact that as you go into something with North Koreans, there are other goals in mind. For example, we had a deteriorating relationship with South Korea. That is people didn't believe we were serious about negotiation, and our reputation was being hurt by that. In going into negotiation with the North Koreans, I think we overcame that presumption among many South Koreans. So you go in with a number of objectives, some of which are clear to the press and to everybody, some of which appear more secondary.

SHAPIRO: This book is full of larger-than-life personalities over the course of your career. I'm curious about the last two secretaries of state that you worked with. You clearly have great respect for both Condoleezza Rice and Hillary Clinton. How would you compare these two secretaries?

HILL: They were certainly both interested in policy. And Condoleezza Rice was very interested in policy issues. But I think it's fair to say that Secretary Clinton was also looked upon as a figure who might come back at some point. So...

SHAPIRO: In some capacity or other.

HILL: I would say so.

SHAPIRO: Who's to say?

HILL: Special envoy, who knows.

SHAPIRO: (Laughter).

HILL: So certainly, you got a sense of a State Department that had a really keen sense of politics as well as policy.

SHAPIRO: Ambassador Christopher Hill is dean of the Joseph Korbel School of International Studies at the University of Denver and his new book is "Outpost: Life On The Frontlines Of American Diplomacy." Thanks for your time.

HILL: Thank you. Transcript provided by NPR, Copyright NPR.