I often have clients say that if one of their children fails to survive them, they want to leave the child's share to his or her spouse, whom they love like their own. While that's certainly a commendable instinct and one that reflects good family relations, here's the rub. If a married child is taken from us much too soon, the spouse may well marry again at some future time, and if that partnership is successful and longstanding, the clients' assets may end up benefiting the new spouse, who, of course, may be a fine person but not a member of our family. My recommendation is usually to recognize the clients' affection for their child's spouse with a meaningful token of their feelings, but to leave the majority of their assets either to the grandchildren - either outright or in trust - or if none, then to the other children or grandchildren. Thinking about far-reaching scenarios is one of the keys to successful estate planning.

Other clients want to leave some or even much of their benevolence to an unrelated friend or caregiver who's provided faithful and vital assistance to them in their final years - perhaps because their actual family members live elsewhere or simply can't provide such help because of their own obligations. Needless to say, when this state of affairs is revealed after a person has passed, the children or grandchildren feel angry and betrayed, and they often express those feelings not only toward their departed family member, but even more so against the caregiver who may have had no idea he or she was going to benefit financially.

If I'm convinced that this is a client's honest wish, and if undue influence or duress doesn't seem to have motivated it, I suggest a couple of alternatives to head off the trouble I know lies over the horizon. Again, I suggest a more modest amount to recognize the caregiver's valuable assistance - which they would likely prefer to a larger amount that also comes with abundant recrimination, if not actual legal action. Or I urge the client to write out his or her justification for the magnitude of the bequest in significant detail and with as much competent explanation as possible. Even a video of the client's decision-making is often a further way to head off a legal challenge or to provide greater insight into the client's thinking.

While we're addressing sensitive topics, here's another. How do you decide when a senior may need to pass the baton of financial affairs management to the next generation, and then how do you make that transition without refighting WW II? The typical warning signs are unopened mail - and not just from Publishers Clearing House, but from banks, utilities providers or insurance companies. I realized that my own father needed help when I was visiting and saw that his vehicle registration was six months past due and that he was unaware of that pretty significant oversight. We crept to the DMV office to rectify the problem, but he was as shaken about it as I was.

Then, what do you do when your seniors rationalize each of these telltale clues and turn into the masters of denial? The best practice I've seen is one that's gradual and non-confrontational. If you can have regular enough contact, you can certainly monitor the mail and suggest that you work together to make sure all the monthly checks are being written and mailed. If that becomes a comfortable exercise, then a moment usually arrives when the torch will be passed without incident. If the distance involved precludes that process, then consider contacting - and compensating - a parent's trusted friend or the assistant he or she has long dealt with at an accounting or investment firm, and see what you can arrange. My mother had a wonderful woman who worked for her CPA and who came every week or two to eat ice cream with her and, oh yes, take care of the necessary finances. She was a life saver, and this reminds me to contact her and thank her yet again.