How to Pass Down Values, Not Just Wealth | Dan Pascone with Ashish Khanna | Ep #56

Most executives treat estate planning as finished once the will, trust, and beneficiary forms are signed. Ashish Khanna, a former estate attorney turned wealth advisor, explains why that's only half the job: the research on family wealth transfers points to human factors, not technical ones, as the reason money and meaning don't survive the handoff. The fix isn't another document. It's a handful of specific conversations, started on purpose.

Ashish Khanna spent years practicing estate law before moving into wealth advising, and the shift came from a pattern he kept seeing. Families would come in with a fully executed estate plan and still fall apart once the money actually changed hands. A trust told everyone where the assets would go. It never told them why.

Research from the Williams Group, a firm that studies why family wealth transfers succeed or fail, backs this up with numbers Ashish cites often: about 60% of failed transfers trace back to a breakdown in family trust and communication, another 25% to heirs who weren't prepared to receive or manage the money, and 10% to families with no shared sense of purpose for the wealth. Add it up and roughly 95% of the failure is a human problem, not an investment or legal one. The Williams Group's own research is worth a look if you want the full breakdown.

Across the families Ashish has advised, the same four patterns show up again and again, even in families who did everything a good estate attorney would tell them to do:

1. The silence pact: money is treated as too private or too awkward to discuss, so nobody brings it up until a crisis forces the conversation.
2. The information asymmetry problem: one generation knows the full picture and the next generation knows almost nothing, which leaves heirs guessing at decisions they eventually have to make themselves.
3. The illusion of documentation: a signed will and trust get mistaken for family readiness, when the legal paperwork and the family's actual ability to handle the transition are two different things.
4. Assumptions replace conversations: without real discussion, each family member fills in the gaps with their own story, and those stories rarely match, especially once grief is involved.

Any one of these can derail a transfer. Most families we see are dealing with two or three at once.

Ashish points to a moment early in his law career that changed how he thought about this work. A client's husband got seriously ill, and his wife sat across the desk and asked the only question that mattered to her: are we going to be okay? Ashish had drafted a technically sound will for that family. It couldn't answer her question. That gap, between a legally correct plan and a family that actually feels secure, is what pulled him out of law and into advising.

It's also why wills and trusts get treated as the finish line when they're really the starting point. The documents move assets. They don't transmit judgment, context, or the reasoning behind a decision, and that reasoning is usually what the next generation needs most.

When Ashish takes on a new family, he doesn't start with account statements. He starts by mapping what he calls the family's human and intellectual capital: who's in the family, how are they actually doing, what's the dynamic between siblings or between parents and adult children, and what does everyone assume the wealth is supposed to accomplish.

That mapping usually surfaces the real risks long before a spreadsheet would. A sibling rivalry that's been simmering for a decade, an adult child who has never had to manage money, a parent who assumes everyone already knows the plan: those are the things that break a transfer, and none of them show up on a balance sheet.

None of this requires a perfect script. Ashish's advice is to start smaller than you think you need to:

• Schedule one conversation this month built around a single question: what do we want this wealth to do for our family?
• Share the reasoning behind your plan before you share the exact numbers. Heirs need the why more than they need the dollar figure on day one.
• Put a family meeting on the calendar once a year, even if the first one is short and a little awkward.
• Bring your advisors into that conversation once trust is established, instead of leaving them to explain the plan after you're gone.

The goal isn't a perfectly polished family communication plan. It's replacing assumptions with an actual conversation, which is exactly the gap our guide to talking with your kids about money walks through in more detail.

There's one piece of this that's pure mechanics, not communication, and it trips up even families who've done the harder work. Beneficiary designations on retirement accounts, life insurance policies, and certain other assets override what's written in your will or trust. If you named a beneficiary in 2009 and haven't looked at it since, that outdated form controls the outcome, not your current estate plan.

This is a five-minute check with an outsized payoff: pull up your 401(k), IRA, and life insurance beneficiary forms and confirm they still reflect your actual wishes, especially after a marriage, divorce, birth, or death in the family. Our breakdown of what actually controls your money covers where wills, trusts, and beneficiary forms each carry legal weight, and where they don't.

Here's the piece most high earners get backward: they treat the illusion of documentation as a paperwork risk instead of a family risk. They assume that once the estate plan is signed, the hard part is over. In Ashish's experience, signing the documents is usually the easy part. The hard part, and the part that actually determines whether the wealth survives intact, is whether the family has had the conversations that make the documents make sense to everyone who has to live with them.

Put another way: a complete estate plan and a prepared family are two separate projects. Most planning processes only do the first one.

[VERIFY: composite, anonymized example] Take a couple we'll call Mark and Renee, both in their early 50s. Mark is a division president with a base salary north of $400,000 plus annual equity grants, and the couple has a properly drafted trust, updated wills, and a $3 million portfolio split across retirement and brokerage accounts. On paper, their planning is done.

What isn't done: their two adult children have never seen the trust, don't know there's a succession plan attached to it, and have never discussed what their parents expect them to do with an inheritance. When Mark and Renee finally sat down with their kids using Ashish's approach, the biggest surprise wasn't a number. It was learning their older daughter had been quietly avoiding her own retirement saving, assuming the inheritance would take care of it, a silence pact neither generation realized they were keeping.

This conversation is for corporate executives and business owners in their 40s and 50s who've done the technical work, the will, the trust, the beneficiary forms, and want the family side of the plan to actually hold up. If your estate plan is signed but you and your family haven't talked about what it means, this is the gap worth closing next.

A signed estate plan is a good start, not a finish line. If you want help turning your will, trust, and beneficiary designations into a family conversation that actually holds up, a Free Wealth Strategy Call with Tailored Wealth is a low-pressure place to start.