Our expert says:
Thanks so much for the feedback, I'm so pleased to hear you are feeling better.
It is always so wise, and such a relief, to recognize the value of letting go of attempts to control things that are uncontrollable. Its the King Canute Syndrome, I suspect !
If the associate is getting too greedy, of course you should stop spoon-feeding him promptly. Loose the spoon !
Your present approach sounds wide, and good not only for you, but for him, too. If he is to succeed at anything at all, he has to discover his own weaknesses and inadequacies, and to learn to solve his problems himself.
Don't think of yourself being cruel in letting hi "suffer", it's called Discovery, and Learning.
Except in genuine emergencies, no properly run office should rely on anyone working overtime.
Even if you are resigned to remainin a control freak ( and you don't have to ) you will never be a successful control freak, unless you learn to work only on controlling the uncontrollable, and not the freaking uncontrollable !
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