This piece is part of a roundtable with Post columnist Steve Pearlstein and four of our On Leadership expert contributors about the leadership questions surrounding Gen. Cartwright’s pass-over for promotion to chairman of the Joint Chiefs of Staff.

Most leaders in and out of the military have read enough leadership and management books to know that they are supposed to say they welcome and encourage dissent, out of the box thinking and constructive negative feedback. Most probably think they actually do welcome and encourage it. Yet in fact, when it comes to the big issues when it counts the most, most leaders demand that the top team get with the program and view habitual dissenters as not having the “team player” gene considered necessary for implementation of the organization’s strategy.

 There are really two questions here.

One is how to maintain a leadership culture that nurtures independent thinking and forceful advocacy of minority views. It requires a leader who is emotionally and intellectually secure to foster such a culture and who really works at communicating to the dissenters, in word and deed, how much their sticking their necks out is appreciated. One way—and an essential way—that such appreciation needs to be communicated is to promote the best of the dissenters to appropriate positions high in the organization.

It is a separate question as to whether you want such persons at the very top of an organization. The reason is rather ironic: They tend to be quite intolerant of dissent themselves.

For President Obama, the trick is to keep someone like General Cartwright close at hand and deeply involved in the policy discussions at the White House, while finding someone like General Dempsey to be chairman of the Joint Chiefs, his key interface with the military leadership. A chairman of the Joint Chiefs won’t like that and, at some point, will inevitably complain about it, reminding that it is his job alone to be the principal military adviser to the president and the country’s civilian leaders. Which is why would have been equally important that President Obama make clear to General Dempsey, right up front, that principal adviser doesn’t mean only adviser and if he couldn’t live with such high-level dissent, he shouldn’t take the job.