This publication takes views from four different firms about how to frame conversations with clients about what they must do after their demise; the appropriate structures, how to communicate with younger family members, and more.

It may be thought that the hardest part of an estate planning conversation is talking about mortality.

But while advisors tell Family Wealth Report that getting over that topic can be uncomfortable, it appears that there is no clear pattern to how wealth planning conversations proceed in the US today. Attitudes are as varied as the US population in general – and that’s a lot of variation. 

“Nearly everyone is uncomfortable thinking about their own mortality, let alone discussing it, which is likely why so many people do not have an estate plan,” David Handler, trusts and estates partner at law firm Kirkland & Ellis told FWR in a recent interview.

“People are more accepting of the mortality of others, such as their parents, and are sometimes the ones encouraging their parents to do an estate plan.”

“People don’t want to discuss uncomfortable topics with their children and potentially create strife in the family. Advisors should include a short explanation in the will or trust for the disparate treatment either to support what was previously communicated or to explain for those clients that don’t communicate,” Handler said. 

“In my experience, people are uncomfortable speaking about death particularly younger generations. Mortality is a difficult topic for so many people to face, and it's a particularly troublesome topic for those that are young and feel immortal,” April Rosenberry, managing director of family office services at EP Wealth Advisors, said.

“To plan effectively for these types of death-related questions, it is important to earn trust from the individual and families to then initiate a meaningful conversation. We start by listening, intently listening, to what is on the mind of an individual or family member. We engage the older generation by understanding their legacy – what is the legacy a parent wishes to leave? 

“And then turning to the younger generation to understand their hopes and dreams. We blend those together and make a recipe surrounding legacy and wishes.  And suddenly, the conversation shifts from something that may have felt heavy or scary to something lighter, hopeful and future-focused,” she said. 

Steve Lockshin, chairman and co-founder of Vanilla, a provider of digital estate planning software, said he could not generalize about people facing their own demise.

“It’s a mixed bag. Some people avoid the topic like the plague, and others are indifferent to the discussion. The discussion of younger people (which I define as 20s and 30s) around legacy/inheritance is nonexistent in my experience,” Lockshin said. “And, unfortunately, when it does come up with old children of wealthy parents, the topic of stewardship is rarely addressed. The focus tends to be on (a) upgrading their lifestyle or spending the money, and (b) how to make more money with the money.”

Sharpening conversations
More than five years ago, the world was rocked by the pandemic, and it sharpened awareness that life is fleeting, and it is unwise to leave a tangled mess of financial affairs for succeeding generations to handle. A rising generation is coming into ownership of tens of trillions of dollars in wealth, some of it in illiquid form – including operating companies – necessitating conversations between generations. Not all dialog is easy. There are ways families can avoid inheritance conflicts, for example where one child runs the business and others want an even split of the money.

“Sometimes there are enough assets to leave the business to one child and other equivalent assets to the others,” Handler said. “When a client is going to treat children unequally, I recommend they disclose and discuss it with their children to avoid surprises, and potential claims that they were influenced by one child. It also gives the children a chance to be heard and possibly change the client’s mind. It is sometimes easier to sell the business and divide the proceeds, especially if the children are not involved in the business.”

Communication is key, said Lockshin.

“There is no substitute for good parenting and good communication. There is a saying that, `What’s fair is not equal and what’s equal is not fair.’ This can come in many forms. For example, college is offered to every child debt-free; one graduates from Harvard, and the other goes to a community college for one semester. Both had the same opportunity but with very different costs. Should they be equalized? I would suggest not,” he said. “When it comes to the family business, employees should be treated as employees and shareholders as shareholders. Said differently, if one child works in the business, they should be compensated as any other non-family member would be compensated, and that may include equity.”

Rosenberry agreed about the communications point. 

“In my experience as a former litigator, I’ve seen firsthand how important clear communication is in avoiding inheritance conflicts. Information is key. Especially when a closely held family business is involved, it’s critical to have things in writing to outline the 'how we got here’ story and involve family members in the planning process.

“For some families, ongoing wealth governance meetings facilitate estate planning information discussions. For other families, parents may leave detailed distributions within their trust or other estate planning documents. Sometimes, the most fair and peaceful solution is to sell a business rather than perpetuate tension between co-owners or misaligned expectations around 'sweat equity’,” she said. 

“One of the most touching and consistent concerns we hear from clients that are parents is the desire to treat their children fairly and equally. That’s not always easy, particularly when different types of non-liquid assets are involved or when one child is actively working in the family-owned business and others are not. In those cases, we look at equalizing payments or strategies such as lifetime gifts of certain asset types, or `true-up’ or tailored distributions upon death to help balance the scales as closely as possible,” she said. 

Daunting
Another challenge is that estate planning is complex and comes freighted with arcane jargon. A related point is that laws change, often rapidly and keeping pace is demanding. 

“Don’t overload clients with bulletins they won’t understand. Reach out with practical information about actions they should consider taking or changes they should consider,” Handler continued. 

In surmounting the natural desire to delay and prevaricate, Robert Stern, vice president and echelon wealth strategist at RBC Wealth Management-US, said his firm favors a gradualist approach. 

“The aphorism `How do you eat an elephant? One bite at a time’ informs the approach we take with navigating sophisticated estate planning. Clients are more responsive to an experience that breaks down a very complicated process into manageable steps,” Stern said. “We also begin the conversation about wealth transfer with questions to understand the clients’ goals, and fears, which helps us connect clients with what is most important to accomplish, or to avoid. Another important element in helping clients to act is to make sure our clients understand the strategies. Using plain English instead of legalese helps demystify the process, putting clients at ease.”

Handler gave his own swerve on this point. 

“Explain the impact of not having an estate plan, that the assets may not pass to who they want, and how much could be lost to taxes in some cases. Don’t constantly say `When you die…’– focus on the allocation of assets, how they will pass, and under what terms. Focus on lifetime planning and how it can benefit children and grandchildren now,” he said.

Lockshin said that while good parenting and communication are essential components for the successful transfer of wealth, people often procrastinate for a host of reasons.  

“Advisors can help clients by making this topic one of frequent discussion and should have a checklist or playbook of the important planning tasks to accomplish and work hard to accomplish these,” he said. 

Rosbenberry explained her approach.

“Estate planning can feel overwhelming given the layers of complexity that come from federal tax laws, state probate and other laws, and even certain state estate-taxes. The interlocking cause-and-effect between different planning choices can make it hard for families to know where to start. It’s no surprise that many people experience a mental barrier to entry and even decision paralysis,” she said. 

“That’s why we approach every process with a conversation with simplicity and compassion in mind. We start by listening; we seek to understand what overall estate outcome the client hopes for and what their biggest concern might be. From there, we begin to narrow our focus on answering those initial, key concerns quickly and clearly,” she said. 

Structures and tools
There is a wide array of trusts, life insurance structures and other ways of protecting and transferring assets. What’s the best approach to showing clients how these work?

“In working with clients on their planning, it is critically important always to tie strategies to their desired outcomes. Clients' wealth generally goes to one or more of four places: clients spend the money on their own lifestyles, they give it to people they love, to causes about which they are passionate, or lose it to taxes,” Stern said. “We take clients on a guided journey of self-discovery to uncover which of those potential outcomes align with their wishes and which they would like to avoid.”

“Communicating in plain English about what happens to a client's wealth if nothing is done versus the benefits realized from implementing one or more strategies can be highly motivating. We also view this as an ongoing process, not a transaction. To us, that means meeting with a client and their other professional advisors to bring an ongoing team approach to meeting the clients’ needs both today and in the future,” Stern said. 

As for Handler, he cautioned against the idea of overloading clients with solution ideas that might not be needed. 

“An advisor’s goal should not be to educate clients on every solution available in the marketplace. Instead, it should be to understand their goals, suggest the tools and structures available to meet those goals and explain the structures in words they understand. There is no need to go into all the alternatives that are not under consideration,” Handler said. 

Rosenberry explained her approach to the tools of the trade.

To walk families through the complexities, we always start with a conversation and questions such as: `What’s your concern around a particular asset?’ `What’s the lifetime goal of this asset?’ `And how do you envision your beneficiaries interacting with this asset after you pass?’ For example, perhaps the questions may be `Is this a keepsake piece of real estate you want your family to gather in during the holidays for years to come?’ or `Is this a startup company that you see as a revenue generator that could be spun off in the years to come?’

“Depending on the clients’ answers, we collaborate internally on the overall planning and then with estate planning attorneys and CPAs to align the clients’ wishes with the most tax-efficient and effective structures for their situation. We never let the tax tail wag the dog so to speak. Instead, we take a methodical, meaningful approach, peeling back the layers of intertwined decisions, exploring options, and finding the right fit. It’s about clarity, simplicity, and honoring the client’s vision,” she said. 

Philanthropy
Philanthropy arises in conversations with HNW clients – and that can be particularly the case in the customary “Giving Season” around Thanksgiving in the US. 

“It is as high up on the agenda as the client wants it. I ask if they have charitable goals during life and/or at death and then explain the benefits and options to achieve them,” Handler said. “I am careful not to make clients feel badly if they want to leave all their assets to their family rather than charity.”

Stern said philanthropy and impact are important conversation points. 

“Using wealth to make an impact and build a legacy is a critical planning topic for many affluent families. When meeting with clients, asking them to prioritize the recipients of their wealth helps to define the path of conversation,” he said. “Where clients feel strongly about philanthropic impact, we often move that element of planning to the top of the list of goals and focus on those strategies. That might mean helping clients think through establishing their own charitable foundations if they want to run a charity, or leveraging a donor advised [fund].”

Advice squeeze
There is a shortage of advice available in the US in general on such topics, Handler said.

Many of those with qualifications work as internal advisors at asset managers, for example, he said. “There are former practicing attorneys that are not giving legal advice any longer,” he said. “In the financial services industry, everyone wants to go upstream in terms of client wealth – that is where the fees are.”

In the US, there are about 600,000 households with a net worth of $20 million or more; given the current size of the qualified legal profession, there are not nearly enough attorneys to serve them, he said.

“I see what malpractice could be [such as poor advice and lack of advice at all] on a routine basis,” Handler continued. “We have had cases where we have had to undo the estate planning structures put in place by prior counsel.”

Technology
Technology is an ever-present topic in wealth management, and estate planning is no exception. 

“Technology is rapidly transforming estate planning from a reactive (and sometimes unpleasant) experience into a proactive and progressive one,” Lockshin said. “AI enables the near-instantaneous understanding of someone's documents, auto-generating diagrams, and providing a layperson's explanation of an estate plan.”

“Intertwining balance sheet information with an estate plan now allows for contemporaneous planning suggestions and calculators. Document generation tools have democratized and modernized the creation of essential estate planning documents. What has historically been an antiquated process is quickly becoming simplified and accessible to everyone,” he added.

Handler said that AI has its uses within certain limits.

“AI cannot currently draft the complex trusts that we use, but AI can help produce summaries, explanations, charts, and illustrations. For simple estates without tax issues, AI could likely produce a decent will, but I would not sign one that has not been reviewed by an attorney,” he added.

Finally, this news service asked Rosenberry about the impact of the recent One Big Beautiful Bill Act legislation that has, at least for the moment, ended speculation about gift and estate tax thresholds.

“We were in an estate tax limbo for the past few years, with an anticipated estate tax exemption on the horizon. However, with the clarity offered by the One Big Beautiful Bill about the estate tax exemption as of 2026 (what I call a 'sunrise’), we’re seeing a noticeable shift in how families approach estate planning. 

With certainty around the federal estate tax exemption, many clients in the high net worth and ultra-high net worth space are more inclined to take action in the coming year to lock-in the estate exemption and put that part of their advanced estate planning into motion for the 12 months beginning in 2026,” she added.