How to Talk Money with Family

1. DO take action and initiate the conversation.

First thing first, you need to get that meeting on the books. A crucial mistake Americans make is they think the easiest path to success is to just bring up the conversation at the next family gathering. "I'll catch Mom and Dad while they are cleaning dishes after dinner." Good idea, right? Reality check: even during dish time, conversations get interrupted. That said, dish time may be that quiet, private opportunity to ask to meet the following week.

2. DO find a comfortable place to talk.

If you make it past step one and achieve success in getting your parents to commit to a sit-down, don't recommend a coffee shop or other public spot. They will be most comfortable in their own home, and, pending you are within driving distance away, that's where you should meet them.

3. DO NOT arrive armed for war.

Nothing will shut down the conversation faster than arriving at your first family meeting about money with printed brokerage statements, spreadsheets, and reports. Instead, bring a sheet of paper with the open questions you'd like to ask (a small notebook works too) and a pen. Show your blank pages, so they can see that you are truly there for a casual, open conversation.

4. DO listen.

Whatever they say, listen sincerely, maintain eye contact, and only write down the important facts. For example, the name of their financial advisor, or if they've ever attended a free steak dinner with an "investment consultant" (hopefully they left with just a full stomach and not a signed annuity contract).

5. DO NOT pry.

If you get push back on something sensitive, then this is a tell-tale signal that you are pushing too hard, too fast. "I don't want to talk about that, okay?" Don't let this kill your crusade. Remember, just having a conversation is a massive step in the right direction.

6. DO keep it simple.

Keep it casual and start with the easy stuff. Maybe the first question is simple, "Do you have a brokerage account where your money is held?" or "Do you currently work with a financial advisor?" or "Do you have a will?" Don't start with, “How much money do you have in your retirement account?”

7. DO stay calm.

As you progress through the conversation, you may hit gold and uncover some deep secrets. At the same time, this newfound information may make you want to scream at the top of your lungs, "HOW COME YOU NEVER TOLD ME THIS?!" Don't do that! Practice your poker face beforehand, promise yourself to stay calm, and rehearse saying, "That's interesting, tell me more."

8. DO volunteer to hire an independent professional.

In the financial planning industry, there is a running joke that being a financial advisor is 90% psychologist and 10% actual financial planning. The more seasoned the advisor, the more experienced they are at having money talks. If you make some headway, but your folks aren't comfortable getting into the actual numbers, then recommend hiring an hourly-based financial planner to sit down with everyone. For example, the XY Planning Network website makes it easy to filter hourly-based fiduciary advisors by location.

9. DO NOT think, "One and done."

If you succeed in getting a meeting and then having your parents open up about their financial situation, that is a massive milestone. Don't push things too far. Rome wasn't built in a day, and neither are wills, estates, trusts, financial plans, or emergency plans. If the conversation is going great, then take advantage of the positive sentiment to schedule a follow up meeting for the week after. Alternatively, if you find little success, that's okay too. Offer to "do some research" and get back to them later.