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I've heard the expression "the boss is cheerleading a project" where the boss is not really managing the project, but is just encouraging their people for the project to happen. Where does this come from and why would the boss be the cheerleader when he/she is still the superior?

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Cheerleader here is used in the sense

an enthusiastic and vocal supporter

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Probably the boss himself/herself also has responsibilities towards the project in question, but rather than working on those and mitigating the risks, probably she/he is simply cheerleading without really solving any problems. That's my interpretation.

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    Yes, I think this is an important distinction to make. The boss has backed off of direct management for a project, and maintains involvement only through encouragement, not problem-solving. – Robusto Jun 19 '11 at 17:09
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Philoto gave a definition. As for why a boss would do this, inspiring your team (getting them excited about the project) usually works better than just ordering them to do it because you're the boss.

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A "cheerleader" is a member of a group that is "adjunct" to a sports team that is leading the spectators in cheers for the team.

A boss' job is to motivate the team to get the job done. Sometimes, this result can be achieved by being "bossy," but with a competent, self-motivated group, cheering the team on can be at least as helpful. This sometimes occurs when the boss is, or feels less technically competent than the team members. Eighty-three year old Warren Buffett, chairman of Berkshire Hathaway, plays "cheerleader" with his top executives.

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