If you’ve made a will or created a revocable trust to organize your affairs, I applaud you. You’re ahead of about 50% of your fellow citizens.

Still, keep in mind that some of the most important but often poorly considered estate planning decisions are those about who to designate to make heads or tails out of your final estate/trust wishes and to work on those issues with the rest of your family members. And I know that because we’ve just experienced a couple of “unfortunate” choices for those critical roles that have made the estate and trust administration process for those families “unpleasant,” shall I say.

You may be thinking that the worst choice for important jobs like executor or trustee would be the child of decedent parents who has very little business or financial experience and couldn’t tell a good decision from a bad one. Conversely, you may also be thinking that the best choice would be the child who’s a lawyer or investment adviser and works in the legal or financial arena for a living. Sorry to say – especially about lawyers – but that thinking is often the root of a disaster ahead.

And when you really think about it, the reason is simple. That’s because very few of these situations require the legal or financial acumen you’re counting on your most brilliant child, brother or niece to bring to bear. What you need instead of the know-it-alls, who may have gotten where they are in their personal or professional lives through aggressive, take-charge, even arrogant MOs, are those rare souls who can get along with all the players, who are fair and reasonable and whom everyone else trusts and respects.

They can hire the lawyers and financial wizards if they need them, but they aren’t nearly as likely to need them as when everyone feels they’re being taken advantage of, bullied, cheated or lied to – and everyone feels the need to lawyer up to protect themselves.

So, looked at from this perspective, you may want to make an entirely different choice for your executor or trustee than you first thought. The situations that prompted this lament certainly would have been better served by this counterintuitive approach, as would the well-intentioned parents who would have avoided rolling over in their wherevers.

Here’s a suggestion about how to test the approach I’m recommending. Have a family meeting where you talk about the considerations I’m advancing. Assemble your candidates and raise the issues among them. Tell them how you’re hoping the process will go.

Don’t be swayed by who’s the eldest, by who has the JD or MBA or by who seems to be the take-charge type. And don’t cop out by naming everyone to serve as co-executors or co-trustees, at least unless your offspring are more likely to have each other’s backs than to engage in power plays. Any other co-sibling scenario is just kicking the can down the road and setting them all up for potential conflict. Of course, your life history with them will count for a lot, and the way they handle themselves during the family discussion will also be revealing.

Then, in order to avoid an awkward conclusion to the meeting, don’t tell them what you’ve decided. You don’t want to create conflict or hard feelings that may affect their own relationships – or theirs with you – before the time comes, and if you tell them and then change your mind, that can add the potential for serious discord.

Instead, once you make up your mind, compose a thoughtful side letter to explain your thinking. You may be able to soften a child’s disappointment by explaining that one seemed too busy to take on the additional responsibilities or lived too far from home to devote the hands-on time to complete the work efficiently. You’ll know what to say and how to do it diplomatically, in the interests of preserving family harmony once you’re not there to be the peacemaker. And that’s goal No. 1, in my humble opinion.

One final tidbit is not to have this kind of meeting when you’re all gathered for a holiday celebration. Those are supposed to be joyous occasions, and they have their own stresses. Plus, you don’t want someone to associate turkey or barbecue with challenging conversations and decide not to come back next year.

Look, I know this can be a difficult process, but so is a lot of parenting. And if you’re a child who’s reading this message with your parents, remember that this is their decision and respect them by being the team player you know is the right way to honor them.

L. Phillips Runyon III has practiced estate and trust law in Peterborough for the past 50 years. He was also presiding justice of the 8th Circuit Court for 27 years.