Crafty Lead-ins for Difficult Conversations

Feb 6, 2023 | Aging Successfully

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Beach rocks with facesWe all know there are some communication difficulties, whether in healthcare or aging. There just are.

There are a gazillion reasons that people do not communicate well. We’re intimidated by our doctor. We don’t know how to start the conversation. We don’t know which way this conversation is going to go. Talking produces fear and even dread for many.

Much of my work involves coaching around communication, sometimes as much as the advocacy and guiding actions. Improving communication is a big part of the ‘How To’ department.

I’ve written and lectured extensively about this and will share some of my favorite tips to help you get into the conversation. 

Knowing how to start is the ticket in for so many people. It’s funny – ‘The Youngers’ (younger loved ones) often say to me that ‘The Elders’ clam up and won’t discuss matters. Elders, in turn, will tell me they can’t get The Youngers to the table so The Elders can express what they want and how things will go. Both camps are fairly represented here in this piece, as are the solutions. 

Here we go, about talking and crafty lead-ins.



Gain agreement – Collect a “Yes.”

In advance of the conversation, collect a Yes or several Yeses. Make a date or confirm it.

“May we sit down this evening?” or “Are we still on for Saturday to chat” (about your upcoming medical appointment, helping me to find a financial planner, to go over the information from the assisted livings, the plans for when Tom and I are away)? Subtle but simple agreements. Collect Yeses. (This technique comes in handy in the next section too).


Get comfy. To the extent that you can, know what makes the other comfortable.

Is the other party in their favorite chair? Are you both sitting down for coffee or tea? Is it a good time of day for the other person, and is the conversation going to occur in a good place, free of distraction?


In the Beginning

Gain Agreement

Take a minute to level the playing field by agreeing that this may be a difficult conversation. Or touchy or emotional.

“Gosh, Mom, I feel odd talking about this.”

“Seems weird to have to make a date to talk about showering…”).

Agreement can be gained right there. You are on a level field. There is opportunity to respect each other and acknowledge that you may be coming from differing positions.

“Frank, we may differ in our ways to achieve this, but I know we can work together for Tammy.”


Agree on a signal to stop. 

Agree on a password or signal to stop or pause the conversation.  That empowers each to stop and levels the playing field. 

Remember your signal and use it.  Katy and her father, an ex-military man, laughingly agreed that if “the going got tough” (one party did not wish to continue), one would salute the other. That signal would then have them pause and decide together whether to continue. They could agree to continue or return later, or gain more information and return…multiple options.


Keep collecting yeses

“So, it’s important to you to remain in your home safely?” (Collect a Yes.)

“And we could both feel better if we worked out how to do that?” (Collect a Yes.

“I didn’t realize that was a priority. Let’s talk about that.” (Okay. Yes.)


Check-in from time to time with the other person or the status of the conversation.

“Mom, are you still feeling OK about this conversation? OK, to continue?”
“Tony, that’s a good question, and we are going to figure that out.”
“I’ll bet you never thought we’d be talking about XYZ in such detail; how are you doing with it?”
“A concession here, a little compromise there…or just a statement like “Here we are, talking!” or “We’re getting through this, eh?”


Time for the Meat: My Top Four Crafty Lead-ins

“It’s Alright Now”

You can catch more flies with honey, as they say. As a practice, start off each conversation by acknowledging the positive and talking about what’s working well. For instance, you might say, 

“I’m glad to see that you moved the cabinet items you use every day down for easy access so that you and Mom don’t have to use a stepladder anymore. That was a great idea.”
“Nice job, jotting down your questions to ask your doctor. -and a list of medications and dosages! Your thoughts are collected and your provider and team will love your preparedness”.

Most everyone enjoys praise, and when your compliments are genuine, it will go a long way. Then, you will have a better opening to project the conversation into the future. You will find most anyone, including The Elders, will be more open to discussions when they know and feel that they are appreciated and supported.


The Consultative Approach

Contrary to the Dale Carnegie school of thought, there are times and situations when people do not appreciate being asked to talk about themselves. As far as elder care is concerned, aging parents may wish to avoid the subject of their own lives altogether, especially if sensitive or private health challenges are involved. On the other hand, parents may be interested in helping their children or grandchildren.  To that end, consider asking for an elder’s advice and focus on your own problem. For instance, you might say 

The Younger: “Now that our family is growing, we need to think about estate planning. We need to think about who will raise our child if something happens to us. Where did you start? How did you choose your attorney?”

More inroads:

Younger: “It’s funny, Mom; at this stage in our life, our house seems full-to-overflowing now that the kids are getting bigger and accumulating more stuff. Do you and Dad ever feel like this house seems big and empty now?”

Younger: “I’m starting to think about retirement, even though it’s a long way off. When you were my age, had you begun to think about retirement? How did you find your financial planner?” (Or attorney, or…).

If you are given an inch, go for the proverbial mile! When your parents begin to share and engage in dialog, ask more questions. Keep tugging on each thread. Above all, be genuine and adopt an attitude of praise.


“Flip It”

Another conversation strategy for avoiding defensiveness is to focus the conversation on someone else. Your parents may bring up the malady of a neighbor or friend from church. This is your time to “flip it” or seize the opportunity. Begin by asking, “What can we do to help?” or discuss what that person might need. Then, flip it: Talk about how your family would manage the same challenge if it happened to you.

When you are flipping, use the uncertainty to lay a foundation for future discussions. 

“Is my number by your phone in case of an emergency?”
“Who has or knows about a key to the house?” 

Employ storytelling. If an opportunity does not readily present itself, you can tell a story about a colleague at work. Make one up if you have to! Talk about Frank and how he had to leave midday to go to Michigan to care for his father. Talk about how his father didn’t have his work number and how there was a delay in reaching him with the news. Then get the family to imagine the colleague’s situation. Wonder aloud how you or your loved ones might manage the same challenge. Flip it.



Sometimes a headline can create a lead-in for a conversation. Let the tv, news, or even gossip usher in the jack. This is especially effective for lowering resistance to talking because parents are often happy to discuss current events. For instance: 

The Younger: “I just saw an article about real estate prices over where you live. Are you seeing a lot of new construction or old ones being torn down to give way to McMansions?” 

Younger: “Did you see the piece on Channel 11 about a local businesswoman scammed out of $15,000? Just by watching it, I learned a lot about scams and what we can do to protect ourselves…”.

See how The Elders respond. Is the neighborhood changing, are older houses being torn down to make way for McMansions? If logic prevails, this might be a good time to discuss getting the most value from the investment in the current home, which can lead to conversations about downsizing or moving in general. As for scams, we can never know enough, and storytelling is a way to newsjack, teach, and plan.


It’s Partnering, not Parenting

Everybody is uncomfortable enough when the roles of The Elder and The Younger have started to reverse, especially if the conversation turns dark and heavy. 

I know a family that began to plan as a family unit. When they began to say the word “unit,” they would point at one another and say “YOU-nit” and giggle, all ages kidding around. They decided to call themselves and their planning conversations “We-nit”, and it stuck. “Better to be a We-nit than a nitwit,” the patriarch declared. Today, the We-nits have been through a few elderly care challenges, and they continue to talk and revisit their plans from time to time. Taking a collaborative approach and keeping it light brings everyone onto the same playing field. A little levity can make a big difference.

There are many different ways to HAVE THE CONVERSATION (a mantra of mine since 2014), and there is no right or wrong way to do it. The key is to start sooner rather than later, be persistent, and be respectful of The Elders’ wishes. If the approaches listed here seem uncomfortable or unnatural, or if it seems too soon to employ, you now have them in your toolkit. Simply stay in touch, keep communication lines open, look, and listen. Sooner or later, an opening will come.