Shortly after the Enron scandle, educator Warren Bennis told the New York Times, "Unlike top management at Enron, exemplary leaders reward dissent. They encourage it. They understand that, whatever momentary discomfort they experience as a result of being told they might be wrong, it is more than offset by the fact that the information will help them make better decisions."
When organizations and people let trouble build, we usually end up reading about. Trouble once uncovered and dealt with early-on, can usually be solved or at least contained.
It is difficult to be aware of everything going on. It is quite common for leaders to find themselves in the position of the last ones to know. Subordinates generally do not like speaking up with any information that could be construed as negative – constructive or not. It will be talked about to be sure, but not to you. A leader must create a climate where the information they need to function effectively gets back to them. Perhaps it goes without saying that a leader must make it clear that there is no threat of retaliation but that they genuinely want to get feedback from those who have their interests and the interests of the organization at heart. Most messages people get are like Samuel Goldwyn’s tongue-in-cheek comment to his staff, "I don't want yes-men around me. I want everyone to tell the truth, even if it costs them their jobs."
It becomes a question about what we value. Do we value the ability to talk to each other about facts over convenient lies? What the leader values will become the culture of whole organization. Demonstrate the need to look outside your comfort zone.
The only way to get good feedback is to ask. Asking for feedback is not easy and not everyone is capable of giving you the kind of answers you seek. Some simply don't want to, aren't aware enough or do not have the right attitude for the request. Over time, surround yourself with people you value and respect that are willing and honest enough to provide you with the kind of constructive feedback you need about youself and the organization or unit you are leading.