If your manager/CEO/supervisor requires training in a certain area, would you confront him about his need for the training?

Yes, i would confront them with much respect, politness & professionalism if it is really indispensable & intrinsic. However the most important part would be " timing (right time & moment), "how to do it", " how to present it to them", "how to convince them" & "how to capture their attention & arouse their desire into buying the idea & accepting the offer", this is very important.Thanx for the invitation

I think its an unethical to confront subordinates in the higher position just to tell they needs to be trained again. It will trigger a certain flames that may cause me  to be ousted from my  job. The better is to suggest a certain performance ability evaluation to come up a better solution for the weakness of the leaders in the higher position. Not me to tell directly because it will leads to lost their trust to me  and to themselves as well, and it will create chaotic  relationship between me and to my immediate superiors. In other words its an insult to their part that they heard an advises from the lower element of the company. And I should always  give respects to anybody specially to my superior not only to their position but I will respect them as a dignified person.

Yes. 

"Boss, how would you like to be a ninja in *certain area?, there's this training, and i wanna be there too". Please let us enroll.

This  would be an odd approach to say directly to your GM/CEO.

May be in suitable circumstances, you can propose that all of you need to be trained in  particular area to attain the organizational goal.

Confront? As in "respectfully, sir, but you need training in such and such (cuz you suck at it)"? Hell no! There is no amount of respect you can cram into a sentence to make up for saying something like that to the CEO. Highly positioned people have big egos, and I would leave it up to their close and dear friends and family to alert them in their lacking..

Generally the management through the feedback from all directions will analyse the training needs of someone above supervisory level. Therefore, colleagues need not bother about this and unwarranted too.

Thanks for invitation,

I will ask to meet with him to clarify the matter, maybe he has a very good reason for his decision or he noticed that some training needs are appeared or he is preparing by this training for some future objectives.

I would request him politely and indirectly..........................

Thank you. I agree with experts & looking forward to new answers. 

Thanks

I would ask him gently to join this training and I will inform him that I will do the same to enhance our skills  

I would rather use soft communication skills to make him realize that we are planning to train few employees in certain area so kindly come and join us as trainee so that employees can be morivated.