Use the backdoor An indirect approach can ease the initial awkwardness. Open by showing an article about long-term care; talk about changes you've made to your will; or remind them of an aging relative's challenges.
Tackle health issues first Find out if they have a living will and a medical power of attorney in case they're incapacitated. Also ask about long-term-care insurance.
Next, address money The key questions: Do they have someone authorized to make financial decisions on their behalf? A financial adviser? A big enough retirement nest egg? And when did they last update their will?