What's best for my children?
A substantial inheritance may liberate your kids from pressing financial burdens. By all means, provide for promised short-term financial assistance -- college tuitions or home down-payments -- that haven't been met. But beyond those, will a large windfall help or hurt your kids?
Will it enable the talented violinist to pursue a symphony career rather than play weddings four nights a week? Or will it enable the son who hasn't yet found himself to give up the search entirely? Does it make sense to communicate your plans now or to wait? Knowing there's an expected influx of cash down the road could allow your kids to take a trip to Australia while they can still climb Uluru. On the other hand, relying on the demise of a loved one for your own financial security can be problematic.
How do I balance need versus love?
Should you leave more to those who need more, or should you leave the same to each regardless of circumstances? Logic dictates that you leave more to the struggling junior high school Social Studies teacher with a stay–at–home spouse and three kids than you do to the unmarried, very successful tax attorney. But when it comes to family, logic often finishes second to symbolism. That may not be just money you're doling out -- it could be love.
I know a very successful recording artist, married to an even more successful performer, who was terribly upset when her parents left more to her two siblings' families, which weren't nearly as affluent. The money was insignificant; the gesture, however, was devastating. Whether you opt to provide equally or based on need, it's essential you communicate your intentions and your reasoning to all your kids. If they have issues, they can take them up with you now, mitigating the potential of a family fall-out at the cemetery.
Who else should I include, and how?
You're more than just a husband and a father. Don't forget your friends. These needn't be financial bequests. In fact, leaving your treasured Mark Messier jersey to your buddy will probably mean far more to him than a check.
Non-financial dispositions like this can and should be spelled out in a letter than supplements your formal will. Consider favorite charities, community groups and your alma mater as well. While you may be tempted to spell out exactly how you want your charitable bequests used -- funding a new digital photo lab for the local Youth Bureau for instance -- there's no guarantee the need will still be there when you’re not. Instead, pick an organization you trust and let it decide how best to use your gift.
Who do I trust?
Wills and estate planning, while savvy steps in the business of living, can also be the ultimate expression of hubris. Not satisfied with exerting as much mastery as possible over our day-to-day lives, we're trying to take that sovereignty with us into the grave or urn. Our motives may be pure, but, as Oscar Wilde once noted, "Whenever a man does a thoroughly stupid thing, it is always from the noblest motives."
That why the selection of an executor shouldn't be taken lightly. Sure, executors are bound to follow the terms of those very carefully drafted trusts and wills. But it's always possible something might happen. The intended recipient of your gold pocket watch could predecease its disposition, for example. Does the executor sell the watch and roll the proceeds into the estate, or pass the watch on to someone else? You need someone who'll respect the text of the document, but not at the expense of the spirit underlying it. Executors can hire professional advisors and managers, so it's crucial they know and understand your heart and mind, not the law or finance.

