How to Make Difficult Conversations Easier



Most people don’t look forward to having difficult conversations, let alone difficult conversations with their family.


Difficult conversations can make us uncomfortable and anxious, so we tend to put them off for "later." Unfortunately, avoiding these conversations doesn't make challenging situations go away, and can make things much worse in the long run.


As our families get older, it can feel like the list of potentially fraught conversations grows disproportionately to the years:


Should dad really still be driving?

Can mom manage her medications?

Can my parents really continue to live safely at home?

What would happen if someone got seriously ill?

Who’s managing the finances?


There’s no guarantee that any conversation will result in the outcome that you desire. However, there are things you can do to increase the chance that a conversation will be productive and avoid hurting feelings in the process. If you approach difficult conversations thoughtfully and with careful planning, you can avoid saying things you might later regret and increase the chances that you will move toward your desired outcome.


  • Don’t put it off. I know you want to wait until after school gets out, after the holidays, or after your spouse’s birthday. Don’t. It’s tempting to procrastinate when you anticipate that an experience will make you uncomfortable. And, if you’re dealing with a serious health condition or early stages of dementia, it’s even more important to have conversations when you have the chance.

  • Set aside adequate time and find a neutral place where you won’t be interrupted. An hour and a half is typically enough to get some work done, but an hour may be more appropriate for older adults who get tired easily. Be conscious of your space. If you are anticipating different opinions, try to meet somewhere private and neutral.

  • Set an agenda to help you stay on track.

  • Get adequate sleep and eat a meal before attempting an important conversation, and encourage other family members to do the same. Our physical bodies directly influence our mental health and emotional states, so give yourself the best chance of cooperation by coming to the table rested and well-fed. Maybe make someone responsible for bringing snacks!

  • Gather everyone together in person. If a family member is unable to attend, set up a video cam (like Skype, Zoom, or Facetime) or arrange for them to call in on speakerphone. This is especially important for long-distance caregivers or adult children/siblings who live out of town. It’s important for everyone to have an opportunity to voice their opinion, be included, and for everyone to hear the same thing.

  • Speak from your own perspective to avoid unintentionally placing blame. Some of the following phrases may be helpful:

“I wish that...”

“I worry about…”

“I feel sad that…”

“It’s important to me that…”

"I was really pleased when..."

  • Listen. When you’re not speaking, give your full attention to what others are saying. It can be helpful to paraphrase what you’ve heard to make sure that you’ve heard correctly.

“What I hear you saying is…”

“So, from your perspective…”

  • Set realistic goals, and don’t expect complex problems to be resolved in one setting. Some conversations will need to be repeated or revisited in successive meetings.

Remember that the reason this conversation is difficult is because you’re discussing something that matters. If it wasn’t important, you wouldn’t care. Be gentle and kind to yourself and your loved ones. They are doing their best, too.


What difficult conversations have you had lately? What difficult conversations are you putting off? A geriatric care manager can help you prepare for a difficult conversation about a loved one’s care or facilitate a family meeting. Ayon Living is a care management practice in the San Francisco Bay Area, and we are happy to help you discuss your options. Call or email today for a free consultation.

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