You see, you need Devils advocates in your team. As an entrepreneur , one of your job requirements is to radiate optimism. To deal hope and part with zest and grit to live and fight another day. 

But you need Devils advocates sometimes to bring you back and ground you in reality for all the things that might go wrong and your optimism is blinding you from seeing the obvious.

But, there is a limit to playing the Devil’s advocate. If they do it in front of the whole team, a team that may psychologically depend on the entrepreneur to push them forth, especially after a failure it ruins the morale of the team and pushes them deeper into the crevice of despair.

The entrepreneurial team, is one which is constantly on the brink of disaster and anxiety and needs to be nurtured with courage, hope and specifically a monomaniacal determination / want to succeed. They must need success as much as they need to breathe.

The devil’s advocate is not needed at idea generation, not needed to give post mortem after a crucial meeting and definitely not needed to say ” I told you so” because its very easy to say ” I told you so” but what’s difficult is the courage to execute an ‘improbable’ plan in the face of the high probability to succeed.

The part where you need the devils advocate is where the entrepreneur feels that everything is going exactly (or) better than how he planned it, which means either that she aimed too low or is clueless about what’s really going wrong. Thats when you really need the advocacy of devil to teach you a little something.