• Should I have expressed my concerns directly with my boss?

This all depends on what type of a boss he was. If he was approachable in the mornings in his sober state then I would have advised that this was a definite course of action. I certainly would have liked to have bounced my concerns off him in a direct approach if my relationship was strong enough to endure a bit of mano~a~mano. I have a feeling that this may have paid dividends. Most people are open to constructive criticism if it is done with subtlety and tact. It depends on his character sans booze and your ability to tread carefully and decisively.

• Was this a matter for HR?

The military approach is always to work through the chain of command. So step I is to approach the boss. Step II would be to approach his direct superior and so work your way up the ladder until you achieve satisfaction. HR would be Step III as far as I’m concerned. It may have yielded good results if his direct superior was approached in a subtle manner with your concerns. He may have had the same concerns, and would appreciate a chance to solve it before some young gun in HR spilled the beans.

• Was it appropriate for me to do anything at all?

Appropriate …………definitely yes. Difficult as the situation is, it is most probably important to do something. Ignoring a problem is not the answer in the long term. I feel that it is important to act, but one should act with subtlety and sensitivity.

• What was the appropriate course of action to take especially considering that I had conflicting loyalties, not only because I liked and admired the man, but because any action on my part could have resulted in career-limiting consequences?

I think that you should have approached him when his mood was a little more receptive. Timing is very important. I would have complimented him on his abilities, and his success, and I would have told him about the aspects for which you admired him. I would then have told him that despite all the admiration there was an area of serious concern. I think that would have been the correct approach. If he was not receptive to that approach, then it may have been time to take it to the next level at HR or his immediate superior.