When and How to Criticize the Boss

"Angry" over Gen. Stanley McChrystal’s candid Rolling Stone interview, Obama wants to hear for himself "what in the world he was thinking."

“Angry” over Gen. Stanley McChrystal’s candid Rolling Stone interview, Obama wants to hear for himself “what in the world he was thinking.”


Don’t we all wonder what the General was thinking? Whether you agree or disagree with why General McChrystal and his Team openly mocked the President and his administration in the interview with Rolling Stone Magazine, can anyone seriously defend the General’s method of communicating his obvious distain and distaste for the President and his administration? And would the General tolerate such public criticism from one of his officers? I think not.

The reality is President Obama is the General’s Boss and while we may disagree with our Boss – in fact should be encouraged to criticism our Boss when appropriate – it is never appropriate for an Employee to disrespect their Boss in the fashion displayed by the General.

So, before you commit a “General McChrystal Type Mistake”, consider these Rules for criticizing the Boss and surviving the experience – maybe:

1. Never criticize your Boss in public! Unless you want to get fired. Or your judgment is so impaired you should get fired!

2. Express your criticism directly to your Boss! When the urge to criticize the Boss strikes you, immediately take it to the Boss. Don’t display your dissatisfaction with your Boss to your team or co-workers because such behavior serves no legitimate purpose and only erodes the team’s morale.

3. Choose the right time to give the criticism! We all react with varying degrees of defensiveness when we are criticized. And the higher the stress level at the time of the criticism, the less likely the criticism is heard. Giving your Boss criticism in the heat of the battle serves no purpose since the Boss will be less likely to react in a positive manner to the criticism. Criticize only when the there is an opportunity for you to talk to the Boss about the basis for the criticism – and it helps to have a good relationship with the Boss before delivering your criticism.


4. Don’t make the criticism personal! Be professional, objective and constructive with your criticism by offering solutions along with the criticism.

5. Be sure the Boss can handle your criticism! Some Bosses don’t want to be criticized, regardless of how poorly they are managing a situation. If the seriousness of the situation warrants it, go to your Boss’s Boss to raise the issue that is the basis for your criticism. No body above your Boss? See Rule # 6 below.

6. It may be time to leave! If you follow these Rules and are not heard, it may be time to quit working for your Boss.

The Bottom Line: Would you tolerate the General’s insubordination from one of your Employees?


While we may disagree with our Boss, as long as we work for him/her they remain our Boss and deserve the respect that goes with the position. It’s unfortunate someone didn’t explain this simple concept to General McChrystal and his Team.

Paul Glover

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