2. Don’t upset them.

Concerns about upsetting Iran’s leaders have shadowed Obama’s policy toward that country since he took office. It was one of the factors that played into the passive U.S. response to the Green Revolution of 2009, and is widely believed to be a reason why the administration won’t act against Syrian dictator Bashar al-Assad, who depends heavily on Tehran’s support to stay in power.

During two years of negotiations, Obama and his international partners agreed to to keep discussions of ballistic missiles out of the nuclear talks after Tehran refused to continue them if that issue was not excluded. But then, at the last minute, they agreed to lift an embargo on ballistic missile technology transfers to Iran when Tehran suddenly brought the issue back into the talks.

Kerry built on that theme in an interview published Aug. 5 with Atlantic writer Jeffrey Goldberg, saying of Ayatollah Ali Khamenei, Iran’s supreme leader that “the ayatollah constantly believed that we are untrustworthy, that you can’t negotiate with us, that we will screw them.”