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Q: My boss, who is about 60, is so disorganised that I wonder if he has early-onset dementia. He can't remember what assignments he's given, what conversations he's had or what deadlines were agreed upon. He'll insist he never received a document he asked for and look truly confused if you offer proof you sent it. He'll tell you to do something and then insist to the point of rage that he did not tell you to do it.

When I started working for him almost a year ago, I thought he was a jerk. But after spending time with an uncle with Alzheimer's, I noticed similarities: anger masking basic confusion, repeated requests and zero retention.

It seems to be an open secret that my boss is incapable of performing his duties. Most of us just work around him. He's been asked by management to be more accountable, organized and transparent, and I suspect he's going to be fired. I'm also experiencing compassion fatigue. It's maddening working for this guy. Should I say anything about my suspicions about his health?

A: My heart is breaking for your boss - but that's easy to say when I'm not on the receiving end of his tirades.

Whether and how you say anything to HR or management depends on your motives. There's no point telling them your boss is failing at his job; they already know - although your input might help them build a case to terminate him. However, if your productivity is suffering because of him, employment lawyer Amy Epstein Gluck of FisherBroyles points out that documenting incidents might help protect your performance record. If you want to alert management about a possible medical cause, Epstein Gluck recommends general terms - "I'm having trouble doing my job because of Boss' forgetfulness, but I'm also concerned it might be due to a health problem beyond his control."

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When dealing with your boss, HR absolutely should not "play doctor," says Declan Leonard of business law firm Berenzweig Leonard. While your armchair diagnosis may be on the money, the employer must focus on an employee's observable behavior and performance, not speculate about medical causes. If your boss tells the employer he has a medical impairment, then under the Americans With Disabilities Act he must be granted reasonable accommodations - digital reminders? a personal scheduler? - to perform his essential job functions. But the ADA offers your boss no protection if he's unable to perform his essential job duties with or without accommodations.

Of course, although it has the right to terminate him for failing to perform those duties, management may choose to transition your boss to a different role so he can continue to have access to health care and other employer-provided resources. Legal obligations aside, there's always room for compassion.