A Journey Worth Taking
Money is one of the most emotionally laden topics to discuss with a family member. You have to realize that the conversation is not A conversation, but a series of trust-building exchanges. It is best to start long before a crisis situation occurs, because that is exactly what you need to prepare for. 73% of adult kids have not had the conversation with their parents. Avoidance? You bet!

The primary thing to keep repeating is that you have their best interests at heart.
Above all, your TONE must stay calm.
Techniques
Here are some tried and true tips that might help you get started. Know thy parent: not everything will work for everyone.
- Schedule a ‘planning meeting’ and have a written agenda if you think that will keep things on track and be well-received.
- Make sure there will be as few distractions as possible.
- Keep the initial conversation as unthreatening you can.
- Ask them for advice on something in your life to break the ice. Even if you know what to do, asking them about how they paid off a loan or got 4 kinds through college can help start a discussion.
- Sometimes it works best to let the closest sibling, the one they would be most comfortable speaking with, start the conversation.
- Determine their biggest fears. Casually ask about what they worry about most about their future, or right now.
- Use an example of someone you both know who either planned or didn’t, and talk about the take-aways.
- Say, “I just saw an article about xxx, how are you coping with that?”
- Sometimes, admitting your own fear around talking about money & why, will help them open up. Nip the objections by putting them on the table to start.
- Ask how you can help them. Start with non-financial things first and then suggest that you can help with tax organization, paperwork cleanout, setting up a filing system, anything to build trust.
It will create some respect and appreciation if you can find some ways to save them money up front:
- Use Medicare.gov to find a better Rx plan, discounts or set up mail ordering
- Review their cell phone plan or cable TV bill
- Help them redeem their credit card points
What You Need To Know
Start by asking for their input about what their wishes are.
What if long-term care were needed?
Would they want to stay in their home and could they afford to given different levels of care?
What are their assumptions about…
• How much different types of caregiving costs: homecare, assisted living, nursing care, transportation, dog walkers, housekeepers, meal prep/delivery, laundry services, etc.
• Where are they assuming they would live if care was needed?
• What would they do if they couldn’t drive?
• How social do they want to be?
Have them come up with a budget, or help them prepare one. Often, financial advisors can help with a spend-down analysis.
Where are their estate planning documents kept? How will their agent or executor get access to documents and accounts when needed?
Who are their important advisors & contact info?
Don’t ask for the keys to the castle, just ask them to work with you to come up with a plan so there can be a transition if or when needed. In a calm voice, paint some what-if scenarios and find ways to plan for the what-ifs.
Our Legacy Organizer Checklist will help you with the details. (Here is our checklist)
Sometimes you find a skeleton in the closet
How should you behave when you find the unexpected? It can be a sweetheart scam, debt you were unaware of, a family member you don’t know about, and so forth.
1. Remain calm. If you get upset or start blaming, nothing will get solved and the conversation stops.
2. Agree with them on as big a part of it as you can.
3. Tell them you want to work together to find a solution.
4. Sometimes outside, professional help is needed. Recognize your limits.
The money talk is a much harder conversation once a parent is on death’s doorstep, but it is still necessary to have.
• Involve them in decisions if they are capable. Don’t talk around them.
• Be direct but compassionate. They are dealing with a lot.
• Find the things you need to know.
If your parents are well-off, their fear will likely be about protecting their assets. For those who are struggling, learning ways to save and get free assistance will calm their fears about running out of money. By trying to stay in tune with their point of view and not your own, you can have ongoing, productive conversations and begin to take the actions that are needed. Good luck on your journey!
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