Non-PRO Homework / test English Social Sciences Social Science, Sociology, Ethics, etc.

Hello! IN what way the questions that the former boss asks the manager are "hard"?In the sense that they questioned the decision he had nearly come to? (Besides, is a mother tongue speaker able, in your opinion, to understand which decision he had come to?) Thx!
"Consider the comment of a manager at CIBC Oppenheimer about dealing with a stockbroker who made a mistake in a client's statement but failed to notify the client:
"I was facing a tough decision about whether to fire this broker or just reprimand him for knowingly violating our policy. I wrestled with it in my head for almost a week and pretty much made up my mind about what I was going to do. But I gave his former boss a call and talked it through with her. She was really sympathetic and knew that I was struggling. She made me talk out my decision and asked me hard questions along the way. We looked at the problem from several perspectives: mine, my boss's, the broker's and the client's."
This manager statement suggests that the goals of the sender and receiver substantially influence the communication process."