The Ultimate Question in Any Decision: Should I?

In the Spring of 1991, Major General Edgar "Andy" Anderson, the commander of Wilford Hall Medical Center, had just learned that one of his recently promoted senior NCOs had cheated on his promotion test.  He called his acting Director of Medical Law, a mid-level JAG Captain (me) into his office, shut the door, explained the situation and said, "What do you think I should do?"  I, eager young buck that I was, went into great detail about the options open to him as the commander, the military justice and administrative procedures to be followed, etc., when he stopped me with a look of slight exasperation and lots of wisdom and said, "Dana, I know what I can do.  I want to know what you think I should do."  Even in his disappointment with the cheater, he was a mentor, a teacher, an example of leadership.

I've never forgotten that, "I hoped for more from you" look, followed by deep mentoring.  The idea of "can, may and should" plays a big role today both in our advising of clients and in my interactions with my business law students.  Simply put, that I can does not mean I may, and that I may does not mean I should.  "Can" connotes ability.  "May" connotes permission or authority.  "Should" deals with things like judgment, ethics, morality and charity.  The first two are largely a matter of fact: when I'm a kid, I either can or can't ride a bike.  I either may or may not ride down to my friend's house.  However, whether I should depends on the weather conditions, or what I'm going there to do, or what time I have to be home.

In estate planning, it might play out as follows: you can hire a lawyer to write a will, and you may give away the stuff you own to pretty much whomever you wish. The "should" sometimes comes when a client wants to, for example, not only disinherit a child, but state in great detail in the will the ways in which that child has disappointed him or her.  That's where we sometimes stop being attorneys and start being counselors.  I'll write your will however you want it within the bounds of the law, but I reserve the right to say, "Is that really how you want to say it?"  In probate, it might be whether to contest a will when all the assets could be depleted in the litigation.  In business, whether to form a company with a friend as "50/50 partners" (almost always a bad idea).  Some people don't like it and we've been fired more than once for making unappreciated observations, but we take seriously the firm motto - "helping people for life". Making a decision in anger, or greed, or out of spite - or even compassion - often gives rise to regret.  The "should" part of the equation is the part we all sometimes need a little help with.