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In my last post about making hard conversations easy (or at least easier), I talked about using humor and telling stories as two approaches that can help when discussing challenging subjects; here are two more tips for you!

Check Your Intentions
This is a big one. And actually one that is very difficult to master because often the people with the most challenges are the same people who really won’t be able to see the problem.

It comes down to this…what are you trying to accomplish?

I don’t mean what you SAY that you are trying to accomplish. I mean what are you REALLY trying to accomplish.

For example, you might say that you are trying to get all your siblings to assist with convincing your dad that it might be time that he stops driving. But the underlying family dynamics is causing a problem because subconsciously you are trying to counter 47 years of feeling like your sister is a control freak and won’t stop telling you what to do.

Because there is so much history and emotions involved, and conversations surrounding aging parents also add a level of fear to the discussion, it is easy for unresolved issues to pop up and overrun even the best intentions.

Knowing and acknowledging the potential problem can often be half the battle – or may even win the war for you.

For me it often comes down to this – the priority is the person at risk. Be on the lookout for pitfalls in the conversations that can sway the original intentions.

For families with longstanding issues, needing to come together to do things for a loved one who can no longer do for themselves can bring long buried grievances right back to the surface.

More than any other challenges to having difficult conversations, this is the issue that I would recommend, if it appears to create insurmountable obstacles, bring in a trained, neutral third party to help.


Know Your Audience
I do a fair amount of professional speaking on the topic of downsizing. The talk that I give is different when I am in front of an audience of seniors who are considering downsizing and when I am in front of an audience of adult children who need to talk to their parents about considering downsizing.

The talk that I give to financial planners about how to help their clients plan for the future of aging parents is often a little different then the talk I give when speaking directly to the financial planner’s clients.

It makes sense, doesn’t it? Different people need to hear different things. And different personalities take in information differently.

So if you know that your mom is very non-confrontational, for example, you should use that information when approaching her about potentially uncomfortable topics.  Or if you know she is “a numbers person” and you want to talk to her about downsizing, it would serve you well to have some of that information handy so you can provide her the specifics she desires such as the general costs of independent living communities in the area.

These two tips both require you to really think about the person you are speaking to – rather than the previous tips that spoke more to how to deliver a message.

Putting your audience (in this case your loved one) as the priority and using what you know about them to help you deliver a more clear and comfortable message can go a long way in getting an uncomfortable conversation well underway – and even dare I say, more comfortable.

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