Essential Questions You Have to Ask Your Aging Parents
October 1, 2021

Think the birds and bees is the most awkward chat you'll ever have with Mom and Dad? Think again. Adulthood brings other uncomfortable conversations: wills, long-term care, and end-of-life issues. Here's how to these handle delicate subjects with care.


The Big Question: Do You Have a Will?

A will determines the future of not only money and property but also pets and even token mementos. When someone dies without a will, her estate is divided in probate court, where a judge decides who gets the assets. This can cost thousands of dollars and take months. Even if the deceased told a loved one her wishes before she died, a verbal statement won't hold up in court. The judge will base his ruling on laws and legal precedents of the state."


How to Bring It Up

"I don't want to upset you, but if something happened to you, I would want to know that your wishes were being honored. Do you have a will?"


While You're at It, Ask…

  • Have you consulted a reliable financial planner who can help anticipate your needs as you age?
  • Will you give me or another trusted person power of attorney over your financial affairs in case there's a time you can't handle them yourself?
  • Do you have an authorized user on your bank and investment accounts?
  • Do you need help handling some of your financial ponsibilities, like double-checking your credit-card statements and reviewing your bills?
  • Are you willing to have a joint checking account with me so I can help you pay bills if necessary?


On Their Living Situation…

The Big Question: Have You Thought About Long-Term-Care Insurance?

Most long-term assisted-living or nursing-home expenses are not covered by Medicare.. And long-term care, which includes anything from extended home assistance to a nursing home, is very costly.


How to Bring It Up

"I read about how much assisted living can cost, and I was stunned. I would want you to have the best care if it ever came to that. Have you looked into insurance?"

While You're at It, Ask…

  • Do you want to live in your house for as long as possible? Are there things we need to do to your house so it's safe and comfortable for you as you age? Can we make some of those changes now?
  • Are you willing to move into a smaller place that's easier to manage, like a condo? When?
  • Have either of you thought about whether you would want to stay in the house if you were alone?
  • Would you be willing to hire someone to help you at home if you can't do it on your own anymore?
  • Would you consider moving in with me or one of my siblings if we all agree that you need help with your personal care or aren't safe at home alone anymore? How do you feel about moving into an assisted-living facility?
  • Can I help you scout out quality assisted-living facilities and nursing homes now, so we know what's available and what you would prefer in case you need one in the future?


On Their Health…

The Big Question: Do You Have Advance Health-Care Directives?

Advance health-care directives can include a living will (which gives written instructions on the degree of life-sustaining measures that should be taken), a health proxy in Massachusetts by Statute (which appoints another party to make health-related decisions in the event that a person is unable to do so), and a HIPPA release (a document that allows another person access to someone's medical records, which is useful for insurance claims). It's difficult to make decisions in a crisis, and memories about conversations differ.


How to Bring It Up

"If you were ever on life support, I would be really torn up and not in the best frame of mind to make a decision. I know we talked about how you feel, but I think it would give both of us some relief if you put it in writing."


While You're at It, Ask…

  • Will you consider giving your doctor permission to talk to us in case we have questions about your medical treatment?
  • Can one of us accompany you to some doctor's appointments? We recognize your right to privacy, but maybe we can help keep track of everything your doctor says at your visit.
  • How do you feel about being kept alive with ventilators, feeding tubes, or other interventions? And under what circumstances would you want that? Do we all understand what these terms mean?
  • If you have advance-care planning documents, where do you keep them? Have you shared them with any family members, doctors, or clergy.
Contact us in Belmont, Massachusetts, at (617) 489-5919 for comprehensive estate planning from attorneys with experience.
By Dale Tamburro July 21, 2025
In recent years, a number of non-lawyers have started offering Medicaid (Longterm MassHealth in Massachusetts) planning services to seniors. While using one of these services may be cheaper than hiring a lawyer, the overall costs may be far greater. The person offering such services may not have any legal knowledge or training. Bad advice can lead seniors to purchase products or take actions that won't help them qualify for Medicaid and may actually make it more difficult. The consequences of taking bad advice can include the denial of benefits, a Medicaid penalty period, or tax liability. Additionally, our experience, having provided services in this area for over 30 years, has shown these non-lawyers have consistently failed: To diligently and comprehensively identify all the assets of an applicant before applying. Do not explain adequately, movement of the applicants’ funds over the five year lookback, which is necessary for the applicant to be accepted by Medicaid (MassHealth). Most do not offer planning advice. In contrast as an attorney, my priority will be to determine what money can be saved, used within the rules and how especially to handle real estate that the applicant has an ownership interest in. Such advice could preserve their home for their spouse and other beneficiaries and save the applicant or their family thousands of dollars, far exceeding the cost of such planning or services for the application that an attorney would charge. If they do provide advice, it could be bad advice, costing the applicant to lose an eligibility date or eligibility all together. A loss of even one month of eligibility could cost the applicant or their family as much as $20,000. As a result of problems that have arisen from non-lawyers offering Medicaid planning services, a few states (Florida, Ohio, New Jersey, and Tennessee) have issued regulations or guidelines providing that Medicaid planning by non-lawyers will be considered the unauthorized practice of law. For example, in Florida, a non-lawyer may not render legal advice regarding qualifying for Medicaid benefits, draft a personal service contract, or determine the need for or execute a trust.  Applying for MassHealth is a highly technical and complex process. It is especially difficult for long term care benefits like coverage for nursing homes. A lawyer knowledgeable about Medicaid law in the applicant’s state can help applicants navigate this process. An attorney may be able to help your family find significant financial savings or better care for you or your loved one. This may involve the use of trusts, transfers of assets, purchase of annuities or increased income and resource allowances for the healthy spouse. In Massachusetts particularly, the application process, although conceptually straightforward, is not. Too often a comprehensive application submitted still ends up on an appeal to the Board of Hearings, which is handled by attorneys for the Commonwealth.
By Dale Tamburro July 21, 2025
When I give Seminars on Trusts, they are long, detailed and I think very helpful to people who want to learn about Trusts. But I almost never cover enough information on your different choices for Trustees and the responsibilities of the Trustee. Like any estate documents they are only as good as the fiduciaries named in them. For a trust the fiduciary is called a Trustee. Trust Administration Basics A trust is established through the creation of a trust agreement. Within the trust agreement, the Donor or Grantor (creator) of the trust must appoint a Trustee. A Trustee can be any qualified adult, including a friend, family member, or professional (such as an attorney). The Donor can also appoint more than one Trustee, making them Co-Trustees or appoint an entity, such as a bank, to be the Trustee. The Trustee’s overall job is to guard the trust assets and oversee the administration of the trust. Administration the trust, however, involves numerous duties and responsibilities, including: The Donor or Grantor of the trust creates the trust terms, and those terms dictate how the trust should be administered. The Trustee needs to have a clear understanding of those terms and is legally required to follow them without deviation unless a term is illegal, impossible, or unconscionable. The Trustee is required to understand the trust purpose, as outlined in the trust agreement, and to make decisions with that in mind. A Trustee cannot allow his/her personal opinion to get in the way while administering a trust. One of the most important aspects of a Trustee’s job is protecting the trust assets. The Trustee is also responsible for investing the trust assets to help the principal grow. Unless the Donor specifically directs the Trustee to make riskier investments, all investments should be low risk and protecting the trust principal should take precedence over growing the trust assets. The Trustee has a duty to keep trust beneficiaries apprised of trust business and to communicate with beneficiaries as necessary. The terms of the trust agreement will dictate how the distribution of trust assets should be handled. The Trustee, however, is responsible for making sure those terms are followed and that the beneficiary receives the distribution according to the terms of the trust agreement. The trust agreement may give the Trustee the authority to make discretionary distributions. If a beneficiary needs funds prior to a scheduled distribution, for example, the Trustee may have the authority to grant that request. A Trustee should keep detailed records of all trust business, including distributions, payment of trust bills, and time spent administering the trust because those records may be needed to defend the trust, justify trust expenses, or even prevent the Trustee from being held personally liable for mistakes made during the administration of the trust. Because a trust is a separate legal entity it may be subject to taxation. Whether the trust must file a tax return and/or pay taxes will depend on the type of trust, the value of trust assets, and other variables; however, the Trustee of the trust is responsible for determining if any taxes are due and who or what should be paying them. If the trust has an EIN then the Trustee must also file the appropriate tax returns and pay or redirect any taxes due. The Trustee must provide an accounting annually to all qualified beneficiaries. Factors to Consider When You Choose Your Massachusetts Trustee A Trustee is in a fiduciary position, meaning that the utmost care must be taken to protect the trust assets and that all decisions must be made with the best interests of the beneficiaries in mind. A Trustee is also required to juggle a considerable number of duties and responsibilities while administering the trust. All of this should be taken into consideration when appointing a Trustee to limit the likelihood of costly mistakes being made by the Trustee. Before appointing a friend or family member based solely on your relationship with that person, consider whether that person has the following essential characteristics: The Trustee you appoint will be responsible for managing and investing the trust assets. Ideally, your Trustee should have a background or education in finance. By the same token your Trustee must understand the trust terms and the state and federal laws that are applicable to the administration of the trust. That makes someone with a legal background an ideal candidate for the position. Your decision should not be based entirely on the fact that you trust someone; however, being trustworthy is certainly a necessary characteristic for a Trustee given that the Trustee will control the money and assets you use to fund the trust. The Trustee is also responsible for distributing those assets to beneficiaries and paying trust bills, including his/her own fee for acting as the Trustee. Your Trustee may not agree with the terms of the trust agreement, but that cannot interfere with his/her job as Trustee. A Trustee is legally required to administer the trust and make discretionary decisions with the stated trust purpose in mind and by using the trust terms created by the Donor without regard to the Trustee’s personal opinion. Consider whether your prospective Trustee will likely create a conflict. If he/she is a member of the family, for instance, will appointing that person as your Trustee create a conflict within the family? Are other family members beneficiaries of the trust, putting the Trustee in a potentially awkward position? What about business dealings that could create a conflict for the Trustee? Whenever possible, avoid appointing a Trustee who will likely create a conflict. People frequently make the mistake of assuming that someone is willing to serve as the Trustee of the trust they create. With that in mind, be sure to discuss the position with a prospective Trustee before appointing him/her to the position. Along with making sure that a prospective Trustee is willing to serve, take into consideration whether the person will realistically be available to fulfill the duties and responsibilities involved in administering the trust. Consider where the person lives or is likely to live in the future as well as his/her existing family obligations. Finally, consider the person’s age and health when deciding if they would make an ideal candidate for Trustee . There are many considerations to think about if you have co-trustees. Often co-trustees are a family member/friend and a professional like an attorney or accountant. There are many good reasons to use a professional trustee with or without a co-trustee. These considerations are different for everyone and should be discussed at the time of creating the trust.