When a disagreement over caregiving and money threatened to divide three siblings after their mother’s death.
A man I’ll call Jim was referred to me by an insurance broker in my business network after his mother died. Jim was the oldest of three siblings. He lived in Los Angeles. His brother David (not his real name)) lived in New York City, while their younger sister Robin (not her real name)) lived in Connecticut, near their mother, who had remained in the family home.
A few years earlier, it had become clear that Mom could no longer live entirely independently. The siblings discussed bringing in a part-time caregiver, but Robin offered to help. At first, the demands were modest - an errand here, a visit there. David helped when he could, but he had a family and a full-time job as a banker in Manhattan, while Jim lived across the country.
Gradually, Robin’s role grew. There were more errands, doctors’ appointments and the everyday responsibilities that come with caring for an aging parent. Eventually, she moved into the family home and became increasingly responsible for their mother’s day-to-day care. No one had agreed that Robin would be paid. What began informally had simply expanded over time.
Two years later, their mother died. As the siblings began settling her approximately $1.5 million estate, Robin said she wanted to be compensated. She believed the time she had devoted to their mother, and the work she had been unable to do, was worth more than $100,000.
Jim and David saw things very differently. Robin had volunteered to help. She had lived rent-free in their mother’s home, and Mom had paid many of her living expenses. There had never been an agreement that Robin would receive additional compensation from the estate. Jim appreciated what his sister had done for their mother, but he was incredulous that she was now asking for more than $100,000. His answer was no.
The problem was that he was having a remarkably difficult time saying that to his sister. As we talked, it became clear that Jim wasn’t reacting only to Robin’s demand. He was also reacting to years of family history.
Jim had long viewed Robin as the “irresponsible one” - the child who had needed and received more help from their parents than either he or David. There was resentment there that had been simmering for years. From Jim’s perspective, Robin was now asking for something more. The question was how much of Jim’s reaction was about the $100,000 demand and how much was about everything that had come before it.
Jim also had difficulty finding the vocabulary to express what he actually felt. We worked on that and role-played conversations, not to convince him to give Robin what she wanted, but to help him acknowledge what she had done for their mother while explaining why he believed her demand was unreasonable.
Once Jim had a clearer sense of what was driving his reaction, we turned to what he actually wanted to do about it. I asked whether there was any amount he would voluntarily give Robin to settle the issue. His answer was $10,000. Beyond that, he was ready to hire a lawyer and, as he put it, send Robin a “go fuck yourself” letter.
Jim discussed the number with David, who agreed. The brothers then asked if I would present the proposal to Robin. I declined because I thought this was a conversation Jim needed to have with his sister, so we practiced it instead.
Jim called Robin and made the offer. She rejected it and hung up on him.
About a month later, Jim and David received a letter from Robin’s lawyer threatening litigation. Jim was furious. His instinct was to fight.
We went back to the question of what Jim actually wanted and what fighting would accomplish. Being willing to go to court didn’t necessarily mean going to court was the best outcome. Jim and David ultimately decided they were willing to increase their offer to $25,000 to put the dispute behind them.
I suggested that the brothers make the offer jointly and in writing: $25,000 to settle the dispute, with a specific date by which Robin had to accept it. Otherwise, they were prepared to see her in court.
They sent the letter, and Robin called Jim to accept. Robin apologized for the way she had handled things. She still believed strongly that she deserved some compensation for the two years she had spent caring for their mother, but she and Jim were finally able to talk about what had happened - about Mom, the emotions her death had stirred up, and the family history they had each brought into the disagreement. They cried.
The estate was settled. Litigation that likely would have cost everyone more than the $25,000 they were fighting over was avoided, and the relationships among the siblings survived.
Robin didn’t get the $100,000-plus she initially believed she deserved. Jim and David didn’t stick with the zero they initially believed was fair. Nobody had to decide whose version of the family history was correct. They found a number they could live with without losing one another over it.
Sometimes the value of a settlement isn’t measured only by what you pay. It’s also measured by what you don’t lose.
Privacy Note: Names, identifying details, places, and certain circumstances have been changed to protect confidentiality. This case is based on an actual engagement and is presented to illustrate the nature of Resolve Advisory's work.