Life, Leadership and Legacy: Preparing for Succession
Picture a company dinner. The family business leader stands up to make an announcement and waves off the prepared remarks: “They gave me a speech, but I don’t need to read it.” The leader goes on to introduce a “new” product that launched a year ago and then calls a vice president by the wrong name. No one says a word, but everyone in the room knows something is off. By dessert, the adult child who works in the business is convinced their parent should no longer be in charge. The leader’s spouse is defensive, the non-family executives are unsettled and employees are trading glances across the tables.[i]
Who can forget the scene from Succession (spoiler alert – skip to next paragraph if you haven’t watched this yet - then go watch it later!) when Logan Roy suffered from a pulmonary embolism and died on his jet before naming a clear successor to Waystar RoyCo? The aftermath was very entertaining but certainly not what we would wish for any of our clients.
There is a reason that disability and death of a business owner make headlines, and it is not just to celebrate the leader’s accomplishments. The departure of a leader may send shockwaves through an enterprise, impacting its clients or customers, employees, shareholders, vendors, lenders and the community(s) in which it does business (not to mention the “rubber necking” mess left behind). Thus, planning for both these events - difficult as we know they may be to discuss and plan around - is vital to a business’s continuity, and, for a family-owned business, family peace and harmony. “Failure to plan has consequences.”[ii]
This article [i] presents research as background for why this topic deserves our attention; [ii] discusses mechanisms for managing truly challenging situations through multi-dimensional and collaborative planning; [iii] summarizes the discussion of a multi-disciplinary group of professionals regarding two topical hypothetical case studies; and [iv] provides concrete tips for engaging around these sensitive topics.
Why We Look Away
Most of us have watched some version of a business, and particularly of a family business, get upended because people were unprepared for both the human and technical dimensions of an urgent succession process. Most of us have clients for whom the technical documents are immaculate, but the human preparation is seemingly half-baked, at best.
"Our desire for leadership to protect and support us makes us reluctant to imagine not having leaders or having leaders with diminished capabilities." - Thomas Gimore[iii]
The reluctance to engage in planning that requires candid conversations about disability and death is not unique to our clients. Indeed, it is hard for others to talk about a leader’s potentially diminished capabilities when that leader is a parent, close colleague, fellow shareholder, mentor or friend. It also is easier for advisors to draft around the problem than to name it.
Consider a cautionary extreme and high-profile case. In the fall of 2021, the FBI arrested Andrew Russo, the 87-year-old head of the Colombo Mafia family, after years of disciplined, hands-on leadership gave way to sloppiness. His associates had seen the decline for years, yet he would ignore suggestions that it was time to make room for the next generation. In the end, everyone paid for his mistakes.[iv] While Russo’s industry is different from those of our clients, the dynamic is not - a long-standing leader is no longer operating at full capacity, many around them notice, but practically no one feels that they can say or do anything.
The Numbers Are Not Reassuring – What the Research Shows
Disability is not rare. According to the Centers for Disease Control and Prevention (CDC), 28.7 percent of U.S. adults report some type of disability. The most common type is cognitive: 13.9 percent of adults report serious difficulty concentrating, remembering or making decisions. Mobility follows at 12.2 percent. Note: these are population-wide figures, not figures for business owners. Still, the figures are a useful counter to the assumption that disability is unlikely compared with death.
Insurance companies are paying close attention to these trends, and accordingly, key person coverage is harder to obtain for three main reasons:
Medical advances have converted many former causes of mortality into causes of morbidity - people survive events that once ended their lives and continue to live (and some lead) with diminished capacity.
Disability risk from "gray" matters - cognitive, mental/nervous, substance-related - has increased, and these are precisely the impairments a leader is least likely to self-report.
Pricing has risen notably.
The succession data points in the same direction. The Pulse of Family Business surveys conducted by Family Business Magazine across three waves from October 2024 to October 2025, found a revealing gap.[v] Looking back, 67 percent of respondents rated their last leadership succession as smooth or very smooth, and 73 percent said they had a plan – formal or informal -- in place for that succession. Looking ahead, however, only 59 percent expect their next succession to go smoothly, and only 39 percent have a plan in place or in development. The average expected time to that next transition is only five and a half years.
Plans matter, even imperfect ones. Among respondents with no plan, 47 percent expected their next succession to unfold seamlessly. But with just an informal or “handshake” plan, that rose to roughly 69 percent. With the gold standard, a formal written plan, that number reached 85 percent. The survey also found that 57 percent of families gave potential successors leadership development opportunities. While family enterprises seem to be committed to investing in the people, by and large, they are not writing down the plan.[vi]
The research shows that family businesses with ANY succession plan (even if it is not formal or written) have far greater success at continuing after the enterprise leader’s departure than those with no plan. Succession plans should do not just focus on death, as the title of this article implies; they should also focus on incapacity as well since our longer life expectancies make disability planning more important than ever. It is the succession plan plus the estate planning documents in combination that create a security net – we will talk more about that below.
The Human Side of Planning
Death as an event gets the documents (wills, trusts, buy-sell agreements, life insurance policies, and more) – and the technical correctness. What is often given short shrift is the human or psychological side of “what happens the day after a leader’s disability or death?” because in the leader’s and others’ minds, it is often hard to conceive of that day.
The practical implication: the scenario for which our clients, their families and enterprises are least insured, least documented and least prepared is a slow, possibly contested, partial decline - not a completely debilitating incapacity.
Estate planners know the death scenario well. Even so, the consequences of a sudden departure of a founder that happens without succession planning in place may ripple through multiple aspects of the lives of every stakeholder for years. It is like an earthquake, the initial impact may be tremendous, but the aftershocks continue to leave people shaken, potentially impacting decision-making, making business partners nervous, reducing the value of the business and generally causing challenge all around.
Disability and death carry the same risks, but disability adds one more: the leader may still be in the chair. Death is a clear event. Disability often arrives gradually and may be disputed. The person experiencing it may be (but is not always) the last to recognize it, and that person often still holds the authority, may still own much of the business and likely has some of the family’s deference too.
Two Case Studies: Opportunity Costs and Using the “Hive Mindset” of Advising
As noted above, the hypothetical scenario described at the beginning of this article was one of two presented at a session at the 2026 Purposeful Planning Institute Rendezvous conference. In that instance, a leader who had experienced decline was still in the business.
The second scenario was about a family-owned enterprise that was considering how to prepare for leadership and ownership transitions across generations. Family members had different levels of experience, interest and involvement with the enterprise. Some were still determining if or how they wished to participate in the future. Conference participants debated two broad paths for the family: [i] devote meaningful time, energy and expense to long-term planning; or [ii] prioritize the immediate needs of maintaining and growing the business.
Participants in the session came from multiple disciplines, different geographies, and different lived experiences. Together, the group worked through the two case studies and applied their collective wisdom to the challenges. Lessons learned are summarized below.
Hive Mind Lesson 1: For clients who do not see the significance of planning, it is important to name the business risk of stasis. Boards and co-owners generally respond to risk framing when family framing stalls. Planning requires time, attention and investment. That time and attention on planning may reduce focus and resources available for the short-term activities of the enterprise, which may reduce analysis of, and investment in, growth or other opportunities. However, deferred planning also carries meaningful opportunity costs.
While either choice (engaging in planning or not engaging) may affect business opportunities, leadership development and family participation in the enterprise, the options need to be raised, with discussion of the tradeoffs, with all family members, not just those involved in the business. If attention is going to be devoted to one child’s growth in a leadership role, that effort should be intentional, transparent and revisited over time.
Hive Mind Lesson 2: Collaboration is often the key to success, in both training the next generation and in drafting any kind of written plan. That may mean that the plan is revisited from time to time, allowing input from younger generations of family members who may not have had the wherewithal to participate when the initial plan was created. This includes having rising generations contribute to the development of the family’s purpose, governance and succession policies. Having broad participation will strengthen understanding and allow everyone to feel heard and valued, which will increase long-term buy-in.
Conversations about the future often reveal prior decisions made in ways that do not serve the enterprise any longer. The planning process should include revisiting outdated arrangements, past ownership decisions and informal succession expectations, e.g., a plan drafted 20 years ago that is now outdated, a decision to allow a non-family executive to retain equity in the business and now that person no longer works in the company, an off-handed comment that a next gen might be “the one.”
Open discussions and expectations about required credentials, education, outside work experience or current involvement for enterprise employment or leadership will lead to alignment and understanding, whereas future leader selection based on assumptions or unknown requirements may lead to resentment and disillusionment.
Hive Mind Lesson 3: As a family and a family-enterprise grow, and the ownership structure becomes more complex, family meetings may provide a regular place for communications, education and share decision-making. Throughout the process, advisors should approach reluctance with curiosity and empathy, recognizing that succession and governance can be difficult, time-consuming and emotionally risky, particularly when the family and the enterprise have competing draws on their time and focus. We also have to remember, will it really be a success if the enterprise succeeds at the expense of the family?
N.B.: Some of the most productive conversations may occur away from the business in a setting that gives the family space to speak candidly. Maybe a family vacation or when the family gathers for a celebration.
Family meetings are one key component, and another idea for our clients to consider is launching a family council to help the family focus on its governance, including procedures on how conflicts will be resolved and employment requirements for family members.[vii] Research shows that even poorly functioning family councils increase family members' sense of engagement (and may increase an enterprise’s chances of continuing successfully).
Hive Mind Lesson 4: Any sort of process should start with thoughtful questions and conversations with the leader and the leader’s spouse (or partner) about what matters most to them, the purpose of the wealth they have built and how they envision the next phase of their lives. It is important to remember that a transition process should not just be about what the leader is leaving. Often, as advisors, we need to paint the picture of what could be, what the leader may be moving towards. Help the leader find a dignified path forward by connecting a reduced business role with a new purpose, including opportunities to preserve the family’s history, the story behind the enterprise (the successes and failures) and articulate hopes for the future through a memoir, recording or other similar legacy project. Nobody steps away from identity (that has been built for as long a time as the leader has built the business) into a void. Let a leader who may be stepping back see that stepping back is in fact moving toward something, not just losing something. Once the leader and the leader’s spouse can envision their future in positive terms, we can ask, "How can we start building a plan?"
Once it becomes apparent that help is needed, the family (together with the attorney, wealth advisor, accountant or any other professional who helped them see the importance of a plan) may begin by building a short list of firms to help determine what is next and involve each family member interested in the vetting. This practice builds buy-in and it educates people like next gens or spouses who may not have been as involved historically in the work of the family enterprise.
Hive Mind Lesson 5: Families may normalize periodic assessment medical or capacity assessments before concerns arise, such as requiring an annual medical evaluation for those over a certain age. Instituting a practice like this before it is needed removes any potential for feeling targeted. Be prepared for conversations to become harder if decline is already underway.
What to Consider Carrying into Your Practice
First and foremost, this may sound obvious but it is worth reminding our clients: disability and death happen, whether or not there is a plan.
Three less obvious takeaways deserve repetition with clients and colleagues alike:
Planning before a crisis protects three things at once: family relationships, the individual's dignity, and the business. After a crisis, one is usually choosing among those three things.
Do not go it alone. No single professional can successfully do this effective planning alone. The value in the session held at Purposeful Planning Institute and in advising clients in succession planning comes from the cross-disciplinary "hive mind" - attorneys, wealth advisors, insurance professionals, therapists, coaches and family-enterprise consultants each seeing a different facet of the same problem. Leaning on one another across professions helps us to best serve our clients’ needs in this area.
Any planning is generally good planning, but estate planning and succession planning must be combined. One without the other is incomplete. A flawless estate plan attached to an unplanned leadership transition and governance plan still can produce challenges such as a fractured family or even in certain cases, a distressed sale. It is so important to understand that estate planning – using techniques to pass on ownership in a tax efficient manner – is one important part of the business succession plan, but it is incomplete without focusing on the human side of planning that answers - who will take over?
Our clients likely will not raise these topics, but we can normalize them - treating death and disability as ordinary, even expected, events in the lifecycle of a business and family, alongside every other scenario for which we plan.
For estate planning professionals, the practical next step is modest. At your next review with a business-owning client, ask the disability or sudden death question directly: if you could no longer lead the business next month, who would decide, how would they know, and what would happen? The answer, or the silence that follows, will tell you where the real planning work begins.[viii]
Megan Helzner is a Principal at CFAR and brings nearly 20 years of industry experience in operations and consulting to her clients in family businesses, family offices, family foundations, professional services firms, as well as nonprofit organizations and philanthropic foundations. She has worked with and inside nationally recognized nonprofit organizations and with notable family enterprises across the United States. Megan focuses on succession planning, corporate and family governance, strategic planning, and leadership development. Her approach seeks to balance rigor with efficiency, practical solutions with research and theory, and curiosity with expertise. Megan has spoken and moderated at conferences of the Family Firm Institute, the Smithsonian, Family Business Magazine, and the Private Directors Association, and as a guest on podcasts about business and philanthropy. She is involved in her local community as a member of LEADERSHIP Philadelphia and The Forum of Executive Women.
Kim V. Heyman is a Director in the Wealth Planning Group at Pathstone, a multi-family family office. Kim focuses on advising ultra-high-net-worth individuals and families on legacy, wealth and philanthropic planning. Before joining Pathstone, Kim had over 20 years of experience advising ultra-high-net-worth families on estate, gift and generation-skipping transfer tax issues, philanthropic structures and special needs planning, most recently (before Pathstone) as a partner in a boutique trusts and estates law firm. She has authored articles and spoken locally and nationally on estate planning, charitable planning and trust and estate administration topics. She sits on the Board of the PEPC. In addition, Kim is Vice Chair of the Strategy & Administration Group (previously the Non-Tax Planning Group), and was previously the Co-Chair of the Fiduciary Administration Committee and the Co-Chair of the Emotional and Psychological Issues in Estate Planning Committee, of the American Bar Association’s Real Property, Trust and Estate Law Section.
[i] This hypothetical scenario was the centerpiece of “Life, Legacy, and Leadership: Preparing for the Business Owner’s Disability or Death,” a session we facilitated at the Purposeful Planning Institute’s 2026 Rendezvous conference in Boulder, Colorado. Audience members included attorneys, wealth advisors, insurance professionals, family business consultants, and others who work with enterprising families. This article shares some of the research we shared at the conference and, more importantly, what the room concluded together.
[ii] Patricia Annino, “Planning for the Sudden Death of a Family Business Leader,” 14 June 2022, FFI Practitioner.
[iii] Thomas Gimore, one of the founders of the Center for Applied Research (CFAR) in his book, Making a Leadership Change: How Organizations and Leaders Can Handle Leadership Transitions Successfully.
[iv] Ana Resende and Dennis Jaffe, “When the Head of a Family Business Is Impaired – and Won’t Step Down.” 21 April 2022, Harvard Business Review. https://hbr.org/2022/04/when-the-head-of-a-family-business-is-impaired-and-wont-step-down
[v] The Pulse of Family Business surveys, October 2024 (n = 344), March 2025 (n = 386), and October 2025 (n = 291). Family Business Magazine with Brightstar Capital Partners.
[vi] The same research suggests that while boards have little direct effect on succession outcomes, they make it more likely that a plan exists in the first place.
[vii] A family council governs the family - not the operating business. It is generally comprised of a representative group of family members whose goal is to organize and manage the family’s shared work. At its best, it creates a regular forum for communication, education, policy development, next-generation engagement and decisions about matters affecting the family as a whole, while serving as a connector between the broader family and those that govern the family’s businesses, investments, trusts, philanthropic vehicles and other shared enterprises.
[viii] We drafted our PowerPoint presentation for the Purposeful Planning Institute Rendezvous conference with original research and writing, including the summary of the attendees’ participation. We used AI to convert our PowerPoint into an initial draft of this article.
