Essays / "Mill says" - Where to get started [4]

I'm a little confused by the prompts my professor gives me. They usually have multiple questions that are hard to relate in one essay. This is the prompt I am working with right now.

Mill says that "no one can be a great thinker who does not recognize that as a thinker it is his first duty to follow his intellect to whatever conclusions it may lead. Truth gains more even by errors of one who thinks for himself than by the true opinions of those who hold them because they do not suffer themselves to think."

Based on the readings and films we have encountered in the course to this point, is there any evidence that politicians can, or do, meet Mill's minimum condition for being great thinkers? Do Sullivan, Walzer, or Machiavelli think that politicians should aspire to be great thinkers? If so, why? If not, why not? Is there any example, so far, of someone who followed Mill's maxim? Does democracy encourage or discourage the kind of thinking that Mill values?

I have an outline with answers to each of the questions but I'm not really sure how to form that into one paper or how to create a thesis sentence based on that. Any suggestions would be great. Thanks in advance.