General George C. Marshall served as U.S. Army Chief of Staff during World War II. In 1939, Marshall chastised his junior officers for their failure to disagree with him about his planning strategies. Marshall told them he did not want yes men on his staff; he wanted officers who were not afraid to question his decisions.
There is an important lesson in this story. At first, one could rationally say that a leader who wants to be challenged can end up constantly fighting his men and their challenges to him rather than leading and achieving actual operational progress. In the same way, one could say that subordinates who challenge their leaders can easily end up being chastised for that very reason.
Approaching leaders and leadership roles involves some risk because leaders yield power and can change lives of their subordinates for better or worse. But in that realm, there is an unavoidable chance of harm and success at the same time.
Effective leaders like General Marshall need a healthy dose of challenge because no challenge guarantees no feedback loop on their decisions when they were wrong. Every leader needs to adjust just as an artillery gunman needs feedback from forward positions on weather a shot come close to target or not, so he can adjust for wind or other variables he may not have visibility into from the top. On the other hand, a subordinate, should accept the risk of displeasing his/her boss when challenging him/her, the risk of being challenged back, the risk of angering his superior or even being fired. This is the only way you can establish a real dialog in trust with your leader with a healthy dose of challenge back-and-forth.
Good luck with the balancing act of shining back your “lights” at the top of the hierachy without turning into an Icarus.