When I was the Executive Vice President at Walt Disney World, I treasured my team coming to me with their opinion. They did not think of me as the big bad boss. They knew I was open to hearing their opinions. 

I told them to keep me out of trouble and not let me make stupid decisions. 

This attitude flowed up, too. Often, I would tell Al Weiss, my boss, what I needed to get work done. 

Part of your responsibility as a leader is to do the right thing. Telling your boss what you know is the right thing. If you know something and don't share it with your boss, that is on you. You are not in your job to get along and get to retirement alive. 

Too often, people are scared to speak up and let their boss know what they thing. If this is you, you are likely overrating the chance of getting in trouble with your boss. 

If you don't have an environment where you can share your opinion with your boss, consider if it is the right place for you. When you hold back, it begins to have an impact on you when you don't get to tell the truth. It gets to you. Maybe it is time to move on.