As a leader of people and teams I want those I lead to understand they have the right and obligation to voice their opinions, even and especially if they do not match mine. We are a much stronger team if we learn to communicate openly. I have five rules for meetings and two of those apply here:

Communicate openly (you are encouraged to speak up)
Let go of outcomes (any idea voiced becomes the idea of the team and up for discussion, approval or dismissal)

When a team communicates openly the decisions are stronger and there is buy-in from the whole team. Here are some other thoughts that are important as you try to communicate with your boss.

Make sure your boss will accept or even listen to what you have to say.
If you have something to say…say it…nicely…constructively
Iron sharpens iron…Dialog is healthy
If you boss will not accept or listen to ideas, it probably is time to look for a new boss.

Malcom Gladwell in his book “Outliers” relates this fact:

“In commercial airlines, captains and first officers split the flying duties equally. But historically, crashes have been far more likely to happen when the captain is in the ‘flying seat.’”

After reading this the obvious question is why? The sad answer is: the captain is less likely to allow critique of his actions and secondly, due to that culture, the first officers are less likely to speak up.

The lesson for all leaders, no matter what they are leading is: a leader is much better when he establishes a culture in which he allows his team to speak freely.

There are times leaders have to step back and make tough decisions that are not popular with the team. If the whole team has communicated their thoughts, then the decision will be much stronger because it was decided through constructive dialog.