Passing It On, Part 2
The Conversation No Family Wants to Have First
June 11, 2026
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Show Notes
Eddie and Betty's Conversation
You know, Eddie, I've been thinking about something since I read Ian Schaeffer's latest piece. He's talking about estate planning conversations, and he puts his finger on something that makes me a little uncomfortable. He says the hardest part isn't the legal stuff or even the money decisions. It's just getting the words out of your mouth.
Right, and he's got some personal experience with this now. He mentions these conversations are getting more real in his own family. I think that's what makes this piece hit differently than the usual estate planning advice.
What really got me was his point about the waiting game. Both sides are hoping the other person will bring it up first, so years go by and nobody says anything. I can absolutely see that happening. As the adult child, you don't want to sound like you're circling around waiting for an inheritance.
And from what our advisors tell us, that silence is the biggest thing standing between families and actually having a plan that works. It's not that people don't care about estate planning. It's that nobody knows how to start talking about it.
So let's say I'm ready to have this conversation with my parents. What's the wrong way to start? Because I feel like most of us would probably mess this up.
Ian's pretty clear on this. The wrong opening line is anything that sounds like 'what am I getting?' That's coming from the wrong place entirely. He says the right approach is more like, 'I want to make sure I can help you, and that I don't make things harder for you down the road.'
Oh, that's such a different energy. You're not asking to see the will or audit their decisions. You're asking how to be useful.
Exactly. He calls it the shift from auditor to ally. And he says that single change is what makes the door open instead of slam shut. Because think about it from the parent's perspective. If your adult child comes to you sounding like they're taking inventory, how would that feel?
Awful. Like they're just waiting for you to die so they can get their hands on your stuff. But there's another problem here too, isn't there? Sometimes parents think they've already had this conversation when they really haven't.
Oh, this statistic stopped me cold when I read it. There was a Pew Research Center survey of over 8,000 adults, and 61 percent of parents over 65 said they had talked with their adult children about how their assets would be distributed. But only 51 percent of adult children said that conversation ever happened.
Wait, so roughly one in ten families has a parent who thinks they've been clear and a child who never got the message?
That's right. Ian says parents almost always think they've said more than their kids actually heard. So the plan might be fine, but the conversation never really happened in a way that stuck.
That's kind of heartbreaking, because it means both sides think they're doing the right thing, but they're completely missing each other. So when you do start this conversation, what should you actually focus on?
Ian says lead with the why, not the will. Our instinct is to ask about documents and accounts and numbers, but he says resist that. Those details come later, and they usually come easily once trust is there.
So what do you start with instead?
With what matters to them. Questions like: What do you want your later years to look like? What are you most proud of building? Is there anything you would hate to see happen to the family after you're gone? You're asking about their wishes, not their balance sheet.
I love that. Because nobody wants to feel like they're being processed through some checklist. They want to be understood as a whole person with hopes and concerns.
And Ian says when a parent feels that you're genuinely interested in what they want, not just what they have, the practical details tend to follow on their own. The trust comes first, then the information.
Okay, but I'm still stuck on the logistics here. When do you actually bring this up? Because I can see myself putting this off forever, waiting for the perfect moment that never comes.
He's got some really practical advice on that. First, don't ambush anyone across the Thanksgiving table. Holiday gatherings are not the place for this.
Oh good, because that sounds like a recipe for disaster. So when then?
Look for what he calls 'the door that's already open.' A story that's already in the room. Maybe a friend whose family fell apart over an estate, or a news article you saw, or a neighbor who just moved into assisted living.
So you use that as a conversation starter?
Right. You can say something like, 'That made me realize we've never really talked about what you would want. Can we, sometime soon, no pressure?' You're not starting a confrontation. You're pointing at something that happened to someone else and gently asking to learn from it.
That feels so much less threatening than just calling them up and saying, 'We need to talk about your estate plan.' But once you do get the conversation going, what kinds of questions actually help?
Ian emphasizes that you want to ask, not audit. The fastest way to kill the conversation is to show up with a checklist and a tone that sounds like an inspection.
So what would good questions sound like?
Things like: Where do you keep the important papers, in case I ever need to find them in a hurry? Is there someone you would want me to call, your attorney or your advisor? Who do you trust to make decisions if you couldn't? These are open questions, and then you be quiet and listen.
I notice those aren't about money amounts at all. They're about logistics and relationships and decision-making.
Exactly. You're showing them that you're a safe person to hand the baton to. You're not demanding answers. You're demonstrating that you can handle responsibility.
Now, what if you're on the other side of this? What if you're the parent and your adult children haven't brought this up? Do you just wait for them to come to you?
Ian writes about this from a pretty personal place, since he says he's in the adult child seat in his own family. But he has some strong words for parents too.
What does he think parents should do?
He calls it 'the gift of going first.' He says your children are almost certainly not going to bring it up, because to them it feels like asking about your death or sounding greedy. So they wait.
And meanwhile, years are going by where everyone's thinking about this but nobody's talking about it.
Right. Ian says when you go first as the parent, you take that fear away from them. You spare them years of guessing and a lifetime of wondering whether they got it right.
That's really beautiful, actually. He says telling your family what you want, while you're healthy and clear, is one of the most generous things you'll ever do for them. It's the difference between leaving them a puzzle and leaving them a map.
I think that's such a powerful way to think about it. Because most parents want to make things easier for their children, not harder. But if you never have these conversations, you're accidentally making it much harder.
So whether you're the adult child or the parent, the message is basically the same: somebody needs to go first, and sooner is better than later.
That's right. Ian says these conversations should happen sooner than feels comfortable, and while everyone is healthy. The conversations that go worst are the ones forced by a crisis, like a stroke or a fall, when emotions are high and time is short.
Because then it's not a conversation anymore, it's an emergency.
Exactly. And people don't make their best decisions in emergencies. They make their best decisions when they have time to think and talk things through.
Okay, so let's say I've worked up the courage to have this conversation, and I've found a good opportunity to bring it up. What am I actually trying to accomplish in that first discussion?
Ian's pretty clear that you don't need dollar amounts to be helpful. You need to know where things are and who to call. So you're looking for basics: where are the important documents kept, who are their attorney and financial advisor, who would they want to make decisions if they couldn't.
That makes sense. You're not trying to get a full financial disclosure. You're trying to understand the framework, so if something happens, you're not scrambling around trying to figure out where anything is.
Right. And I think there's something else going on here too. When you ask those kinds of practical, helpful questions, you're showing your parents that you're thinking about this responsibly. You're not asking 'how much will I get?' You're asking 'how can I help when you need me to?'
That's such a different energy. But I have to say, even with all this good advice, this still sounds really hard to me. Like, intellectually I get it, but emotionally it still feels like such a difficult conversation to start.
Ian mentions something that I think helps with that. He says having a neutral third party in the room can make a huge difference. Families often say things to an advisor that are hard to say to each other.
Oh, that's interesting. So instead of trying to navigate all of this family dynamics on your own, you bring in someone who can guide the conversation?
Right. It takes the pressure off any one person to be the one who started it. Ian mentions that's part of what our team does in inheritance planning meetings. And they have something called a BeneficiaryBox that helps organize all this information afterward, so everything the family needs lives in one place instead of just in someone's head.
That makes so much sense. Because even if you have a great conversation, if all that information is still scattered around or just in one person's memory, you haven't really solved the problem.
Exactly. The conversation is the first step, but then you need systems to keep track of what you learned and make sure it stays current.
I keep coming back to something Ian said earlier though. He mentioned that from the conversations our advisors have, the silence between family members is the single most common thing standing between a family and a smooth handoff. Not the legal complexity, not the tax issues, just the fact that nobody's talking.
It really makes you think about how many families are out there right now where everyone loves each other and everyone wants to do the right thing, but they're all just waiting for someone else to bring it up first.
And meanwhile, opportunities are passing by. The parent could be sharing wisdom and explaining their thinking while they're sharp and healthy. The adult children could be learning what they need to know to be helpful. Instead, everyone's just hoping it will somehow work itself out.
And Ian's point is that it usually doesn't work itself out. These conversations don't just happen naturally for most families. Someone has to decide to make them happen.
So whether you're 45 and thinking about your aging parents, or you're 70 and thinking about your adult children, the message is pretty much the same: have the conversation now, start with care instead of money, and focus on being helpful rather than being informed.
That's a great summary. And remember, this is part two of Ian's series on Passing It On. He mentioned that next he's going to talk about what to actually do when you're the one who inherits. So this conversation we're talking about today is really setting the stage for that transition to go smoothly.
I think what I appreciate most about Ian's approach here is that he's not pretending this is easy. He's honest about it being personal and difficult and uncomfortable. But he's also clear that the discomfort of having the conversation now is nothing compared to the problems you create by not having it.
And he gives you really practical ways to start. You don't have to figure out the perfect words. You just need to find a natural opening and be willing to take that first step.
You know, if you're listening to this and thinking about your own family, maybe this is your sign to stop waiting for the perfect moment and just find a good enough moment. The conversation you have won't be perfect, but it'll be so much better than the conversation you don't have.
And if you want help getting that conversation started, or if you want someone to guide it so it doesn't all fall on your shoulders, that's exactly the kind of thing our team can help with.
If you'd like to talk with one of our advisors about opening this conversation in your own family, you can reach the team at American Retirement Advisors at 602-281-3898. Sometimes the hardest part really is just knowing you're not navigating this alone.