Be wary of family businesses. Dictatorships can indeed evolve into democracies, with Taiwan, South Korea, and Chile being perhaps the three most prominent examples. But rarely, if ever, has a dictatorship changed when it was still governed by its founder or his family. In those cases, the dictatorship is interwoven with a cult of personality, and reform would mean a repudiation of that cult. The Castros and the Kims might allow small openings in their systems for, say, foreign investment, but they will have to leave the scene before there are more meaningful changes.
Be wary of ideological dictatorships. Military dictatorships and other varieties seem more susceptible to peaceful evolution than Communist dictatorships. Absent a governing ideology or a family commitment, the government can be more receptive to change as the leadership grapples with economic and societal pressure.
Dictators are dictators for a reason. They are not unaware of their countries’ impoverishment; they just have other priorities. Regardless of how many Kitchen Debates they participate in or how many movies they are shown, checkbook diplomacy will have limited effect and can even be seen as a sign of U.S. weakness.
Use your experts. Nobody knows better than the North Korea desk officer at the Pentagon that the North Korea government does not honor international commitments it deems not to be in its interests. Nobody knows better than the Venezuela desk officer at the State Department that Cuban support for repression in Venezuela has increased since the U.S. started engaging Cuba.
Don’t fall in love with your initiative. Trump, like Obama before him, believes he has a key to developing a better relationship with a dictator that other presidents lacked. Perhaps — times change and dictators sometimes change with them, so we have to be opportunistic. But perhaps not. Tyrannical regimes are superb at manipulating U.S. public opinion and playing on outside hopes of liberalization. Any U.S. president has to start with a willingness to break off talks. If he cannot walk away from the table, the dictator is incentivized to behave badly. Remember that Kim moved to Trump when Trump wrote Kim to postpone the Singapore summit.
Sometimes no movement might be the best answer. The Kims have frustrated every president since Truman, and the Castros every president since Eisenhower, but not for a lack of ideas or initiative from the White House. If neither regime wants to change, the best the U.S. can do is maintain pressure, minimizing the harm done to ordinary Cubans and North Koreans and the citizens of neighboring countries.
Allies. Allies. Allies. Every U.S president needs to work in an international framework in which our alliances can enhance the likelihood of a successful outcome. Trump should consult closely with South Korea and Japan to ensure there is an allied consensus on North Korea. Obama should have worked with the E.U. on Cuban human rights. When E.U. foreign commissioner Federica Mogherini visited Cuba without a public mention of human rights, the broader American engagement strategy was weakened.
Move incrementally and test repeatedly. Grandiose rhetoric grabs the headlines, but smaller steps allow you to calibrate your moves to the other party’s performance. The U.S. needs to put the other country’s intentions to the test on an ongoing basis. A mixture of carrot and stick will get the best results.
Find the right mix of goals and values. The U.S. values human rights, and we also have core geopolitical interests. We want to stop Cuba from supporting violent revolutionary movements across the western hemisphere, and we want to stop North Korea from enhancing its nuclear capabilities and delivery systems. Keeping human rights in the discussion is important, and stopping the military threat these regimes pose all the more so. Not dying in a nuclear attack is also a human right, after all.
Be careful of the ratchet. The ratchet effect is a phenomenon that can only move one way, or more easily move one way. For example, once the U.S. opens up and staffs an embassy, it is expensive and embarrassing to close it. Once we shut down joint military exercises with South Korea, they cannot easily be restarted because of annual budget and planning requirements. Be careful of making moves that cannot easily be undone.