Political Leanings

Political Leanings is an Institute repeatable side quest in Fallout 4.

Detailed walkthrough
Upon speaking with Justin Ayo in the Institute, he will tell the Sole Survivor that Diamond City's Mayor McDonough is a synth that was put into place to monitor the evolution of the Commonwealth.

Ayo periodically sends someone out to Diamond City to retrieve McDonough's report and asks the Sole Survivor to do this for him. After traveling to Diamond City and finding Mayor McDonough, he will have already been informed that the player was on their way and gives them the report. Once the report is retrieved, return to the Institute and give it to Ayo to complete the quest.

Once given the report, Ayo can also be pushed, with a Speech check, to give a reward of 100 caps.

Bugs

 * If the player successfully asks for a reward from Ayo, then walks away far enough to interrupt the dialogue before Ayo finishes speaking, they will receive the caps but the dialogue is not complete and the quest is not closed. Speaking to Ayo again will allow choosing a different response prior to closing the quest.
 * Sometimes McDonough will not engage in dialogue, but instead talk about how busy he is, and then continue to do nothing. This stops the quest from progressing.