It seems like human nature to wait to tell people our true feelings until they (or we) suffer a near-death experience -- or a really, really bad haircut. Too often, we are forced to face prickly topics at the most inopportune or unexpected times.

Most parents I know summoned the courage to launch into the birds 'n' bees explanation only after their wide-eyed child related some wildly inaccurate tales they heard at the playground. ("Mom, do babies really come from Wal-Mart?")

Life is full of difficult conversations. One of the toughest is talking to a parent or older relative about their final financial wishes.

I for one am not racing to the phone to chat with my folks about their funeral plans and where to find the wills. The whole subject matter gives me the heebie-jeebies. Still, this very topic is on a lot of people's minds, if the questions Tom Gardner and I got at last weekend's Smarten Up: Learn For the Cure conference are any indication. Several women sought input about how to approach aging parents before it was too late.

While it may be difficult to do, having this tough conversation right now is better than the alternative -- digging through stacks of 40-year-old files and guessing at what to do while in the midst of mourning the loss of a loved one.

So, how exactly do you broach the topic? Maybe these general guidelines will give you an idea of an approach that will work best for you:

1. Make it clear that you are having this conversation out of love and concern, not greed. It's not about money and who's going to get what. It's about respecting and carrying out their wishes, and allowing the surviving family to spend the time together celebrating their memory, not weeding through financial documents and second-guessing one another.

2. Explain the consequences of not making their wishes known. Without explicit direction, Uncle Sam may take a healthy cut of their estate, or at least hold it up in probate, dragging the process on. A lot of pain and confusion can be easily avoided by filling out just a few important documents.

3. If a relative is dead set on not dealing with it, there's not much you can do. Hopefully, they have made their wishes known to another family member or their attorney.

If you have other suggestions on how to ease into this conversation, share them on the Family Fool discussion board (membership or free 30-day trial required) so others can learn from your experience (and we can cull the best answers for a Fool special feature!).

I'm not a psychologist, but I do have an inkling that there are some times when it's best to hold off on hashing this out. For example, it's probably not wise to ask if there's an estate plan in place...

  • The week before a family member goes into the hospital for major surgery. At least one month before is probably better timing.

  • When someone is depressed.

  • When bad feelings exist between family members over a recent squabble.

  • Right after watching Terms of Endearment.

Important papers
You want your stuff to go to the people you love -- and to leave a lasting memory as the thoughtful, organized, and efficient relative that you are. The surest way for a loved one to realize their wishes is to simplify the important-paper trail so that the family can effortlessly follow it at a time when they are probably thinking of other things. (Important documents include a will, a living will -- also known as an "advance medical directive" -- durable power of attorney, and medical power of attorney.) TMF Money Advisor members can talk to an Ayco advisor via the financial helpline for guidance on obtaining these documents.

We've all heard stories about family turmoil over an out-of-date will or having someone's finances drained by exorbitant medical bills because no one could find the advance medical directive. As if the emotional drain at these times weren't enough, the split-second decisions that need to be made under duress often end up having a significant financial impact that could have been avoided.

It doesn't have to be that way. A while ago Fool Community member, John Parsons (Parview), posted about his mother-in-law's great final gift to the family. In neat handwriting on a 50-cent school scribbler, she carefully recorded the location of her safe-deposit box keys, the address of her bank, addresses and phone numbers for her lawyer, the details about her bank accounts, insurance policies, credit cards, and more. She penciled in every investment she had ever owned, with the dollar amounts and relevant dates. "She'd even made a couple of comments in random spots in her scribbler from which we deduced that she wanted 'Rock of Ages' played at her funeral," John says.

Though her children -- who were named as executors -- had never looked at the notebook before, they both knew it existed and had been told numerous times by their mother where to find it.

Oh, yeah... John raises an important point. All the organization in the world doesn't mean diddly unless your relatives tell you where to find the list of important papers.

Not everyone has the organizational skills or patience to provide such detailed documentation of their affairs to family members. Author Martin Kuritz makes it easy for the rest of us. His book -- The Beneficiary Book: A family information organizer -- is a three-ring binder-style guide with room to record everything, from your family medical history to the dog's vet's name to a rundown of the safe-deposit box contents. Though filling it out may seem like drudgery, its mere existence can save family and friends countless hours of heartache.

The tendency to protect loved ones from bad news (or to skirt the topic of particularly intimate moments of conception) is understandable. But putting off matters that affect your finances and those of the ones you love will most assuredly make the situation worse.

Consider the psychological benefits of documenting your wishes and telling close family and friends where to find all the necessary paperwork. Share that feeling of enlightenment with your parents and older relatives. Tell the people you love that if they plan ahead, what's left of their nest egg will leave a lasting impression with the people and places that are most meaningful to them.

Once the paperwork is out of the way, you two can get back to your normal activities, like making fun of other family members.

Dayana Yochim gave her parents a copy of The Beneficiary a few years ago. And, yes, they are still on speaking terms. The Fool disclosure policy requires her to admit stuff like that.