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How to Deal with Delicate Family Issues

Dear Joseph,

My sister is the executor of my parents’ estate. When my dad died last May, the estate went to my mom who is living with my sister. Recently, my sister helped my mom re-write her will. The new will leaves all of the acreage of my parents’ property and sole decision-making authority for distribution of all other assets to my sister. When I talked to my sister about our parents’ estate she said she believes no one in the family deserves another dime. I think it is wrong to have such a partial fiduciary for the estate and would like to discuss this with my mother. How should I do that?

A Way for the Will

Dear Way for the Will,

Please hang with me for the next few paragraphs. It might be hard here at the start.

One look at your question leaves me worrying that your sister is setting herself up for big problems—either perceived or real. Either she may play an inappropriate role in the division of the estate, or she may unwittingly act in ways that make it likely you and others will feel that way.

But after a second pass, there are small suggestions that this is a more complicated story with multiple strong and valid concerns. For example, in the facts:

• Since your father died, your sister has had primary responsibility for the care of your mother.
• Your question raises only issues about estate division and not about shared responsibility.

See why I asked you to hang with me? Please don’t take offense. Of course I know nothing—I am only inferring. I believe my primary value to you is not in perfectly understanding the situation but in offering alternative ways of approaching it. These are easier for me to offer due to my detachment and naiveté. So, here goes.

• Focus on what you really want. These situations bring up all of the old victim, villain, and helpless stories of your youth. Perceived inequities, rivalries, and disappointments of yesteryear can be triggered in an instant with the smallest cue. Be very attentive to your own motives—pay attention when you get caught up in winning, being right, avoiding conflict, or punishing. Think deeply about what you really want—for yourself, for others and for the relationships in years ahead. Commit these desires to writing so you can keep them front and center in your mind. I don’t know what is fair or right—but I can assure you that the biggest influence on your future happiness will not be the outcome of estate. Rather it will be your emotions about the estate. And the best way to manage your emotions is to monitor your motives.

• Talk about responsibilities first, assets second. Be sure to think about all of the family issues. Discuss them systemically because they are all connected. For example, don’t raise issues about who gets the farm without validating its connection to who has worked the farm. If your energy is all about asset distribution, this should give you pause to reexamine your motives. If your motives are right, the estate will be an element of your conversation not the soul of it.

• Empathize deeply. Before opening up conversations with mom, sister, or other siblings I recommend you take yourself through a powerful empathy exercise. On various sheets of paper, write the names of each family member who has a stake in these issues. Then, one at a time, become that person. Underneath each person’s name write out their concerns, feelings, needs, opinions—as best you can guess them. Make sure you do this from his or her perspective. You will know you have succeeded in empathizing when you feel a reverence and respect for his or her view while writing it. It will feel reasonable. If the writing exercise provokes resentment or resistance in your mind, keep at it. You’ll get there! The purpose of this process is not to cause you to surrender your own interests or needs. Those are important. It is to simply create space to consider the needs and interests of others.

• Practice rigorous transparency. Now you’re ready to talk. But by no means should you talk exclusively with your mother. The estate is your mother’s so she is the ultimate decision-maker. But because she may be open to influence from others, be sure to avoid creating rivalries by holding closed conversations. Encourage your mother to be inclusive, if that seems appropriate to her. Let all family members know your broader motives. If someone becomes contentious—validate their concerns. Listen deeply. Empathize. Unilaterally commit to getting a fair hearing for everyone. With all this said, I know there are times when feelings are so deep-seated or motives become so clouded that the future could still be painful. But I am confident that if you keep your own priorities right, and approach these conversations with compassion and understanding, you will reach as good an outcome as is possible.

Best wishes,

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14 thoughts on “How to Deal with Delicate Family Issues”

  1. Grizzly Bear Mom

    Dear Sister, when my grandmother died in 1972 when I was 12 I remember my sisters taking her pierced earrings, explaining that I didn’t have pierced ears. Even at that tender age I realized the injustice they were doing. Children don’t have pierced ears but will probably get them someday. Please realize that you may be responding from a position of valid hurt and jealousy, which undermines positive communications with your sister. It seems that the advice provided to you is excellent. You could also pray on it if you are person of faith. Remember, these people are going to be your family for another 30 years and I long to see you live in joy, peace and love with them. Please report back.

  2. Justin

    I too think the advisement is excellent. If, only had the presence of mind to engage “crucial conversation.” I applaud your courage to be forthright.

  3. Joan

    My story is that my surviving parent (My Dad) passed away five years ago. I am the next to youngest child. Third daughter, then our brother arrived 12 1/2 years after me . . same parents. In our Dad’s last years, My middle sister took care of Dad’s financial issues. I was the one who visited Dad the most and cleaned and organized his home. Our oldes sister doesn’t drive, so she couldn’t visit as much as she would have liked. Our youngest brother showed up when he found time in his “busy” life. My oldest sister and I received 1/70th of the distribution of Dad’s estate (if I did the math correctly), because we converted to another religion. We both loved dad and were involved with Dad and the family throughout the years. The “chosen” siblings decided that Dad meant to divide the estate as he did and never offered to “share the wealth.” We “others” would have done otherwise and offered a “fair portion / more evenly distributed if we were the “chosen”. We accept that our siblings are not like us, but we do still socialize and get along with them. Our brother is not a “giving” person, where our sister does pay for family outings when we do get together. Long story short. We do all get along, and are pretty much “over it.”

    1. Grizzly Bear Mom

      Joan you are a credit to whatever faith you joined. I do not believe that most would get over the inequitable distribution of the inheritance.

  4. Kyndra

    I think all children should assume that there will be nothing let of an estate. The cost of taking care of the elderly can sometimes be more than $12,000 a month. If you assume there will be nothing you can be pleasantly surprised when you get anything,

    1. Dawn

      Well said! I’ve seen way too many people complaining about a parent’s estate. Be happy if you get anything.

  5. Liz


    I found I applied a lot of what I’d learned from crucial skills in my own family-will situation. You will learn a lot about yourself and others in following suggestions offered above. A positive is that the increased understanding can help you in making decisions about your own future.

    Even when there are equal shares, there will be people who want more (regardless of need). My experience helped me realize how my own sibs differed when it came to money and I think it was a gift to learn that. Ten years ago I’d have readily given them POA over my finances but know now their priority would be preserving my assets for their inheritance vs my safe care or good life.

    One inlaw is angry that I’m leaving some money to charity (he’d asked me who I was leaving my money to & I’d said ‘sibs & charity’). After my mom ‘s estate was settled, he started asking me how much $$ I had, what he could expect, and who was my financial advisor.

    Had I not had that experience with sibs and my mom’s estate, I’d have made different choices for my own future. Now they are ‘informed choices’.

    Thinking through the process and listening to others’ perceptions was informative. Those crucial skills are truly crucial! Thanks.

  6. Lynn

    I wish that I had seen this great information BEFORE my mother-in-law passed. The “end result” may not have been any different, because my sister-in-law/her family would probably have taken everything no matter what. But I believe that following your advice, my husband and I would have been better prepared, emotionally, to deal with the situation.

  7. BJ

    Thank you for the information and the additional thoughts. I am going through a similar situation with my father, step-mother and step-siblings. Dad is getting more and more confused and I have POA over finances. The steps have imputed motives for both Dad and my financial decisions. We hope to have a meeting soon to try to get on the same page about how to move forward in dealing with a finite amount of assets and an ever-growing monthly rent of over $13k a month in their assisted living facility. There are hard feelings all the way around and emotions run high. This article will help me to have a more balanced approach toward everyone.

  8. Margaret Maxfield

    The article was excellent and so are the comments. Wise people! MWM

  9. Lanie

    I really valued the ideas of how to reflect on where others are coming from – a wonderful tool for a family or work issues.
    They way you are able to broaden the point of view is tremendous, a skill I covet (& am trying to improve). Thank you

  10. Mike

    My wife is a better communicator than I. Had she been asked to respond to the original question, it would have been near verbatim. So saying, my siblings and I had no success. My sister was unprepared to listen. We my Dad passed all was willed to my Mom. When she passed, my sister couldn’t see that we should have received something at least from my Dad’s passing. No amount of rationalizing or mediating worked. Thankfully the probate courts have a saying “Even a dog deserves a bone.” Under great duress my sister reluctantly handed over the small amount determined by the court with a most scathing letter included with our checks. Nearly 15 years later we still don’t speak and each year I receive her Christmas card back with “Return to Sender” and a big F U across the front. Money has a way of bringing out the best in people! LOL

  11. Teddi

    Great article with excellent advice.

  12. Becky

    Good advice. Money has caused a division in our family as well. In the letter, “A Way” didn’t mention how much time, money and effort they put into their mother’s care making it sound like the sister did all the work and “A Way” just wanted the money. Caregivers are often required to give up their own lives to care for a loved one and receive very little from it, which it sounded to me, Joseph, like you were getting at. How many loans did you get from your mother that maybe your sister didn’t get or take. Those kinds of things are often overlooked as well. My mom has to take time every week to help my grandfather with his finances and deal with day to day things even though he lives fairly well on his own. But it is still time and stress on her that the others don’t have to spend because they live out of state. Thankfully, the others are respectful of this and are ok with mom getting a little extra for compensation. I agree, check your motives first before you start pointing the unfair finger.

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