Estate Planning With Purpose

Mar 20, 2024

I’ve spent the past 20 years performing business valuations for my clients. Often, I find myself helping business owners and their advisors plan for ownership transitions, including what happens to their business after they die.

Estate planning can get deeply technical. Talk with an estate planning professional, and you may find your eyes glazing over with talk of GRATs, CRUTs, discounts, crummy trusts, intentionally defective trusts (yes, really), and so on.

Business owners spend considerable time and money working with professional advisors to get these details right. But, often, important human factors are given scant attention.

In my estate planning valuation practice, I have had the privilege of working with some of the best estate planning attorneys, CPAs, and family business consultants in the country, helping them and their clients implement plans that will preserve the integrity of their families and businesses into the next generation.

I’ve also had a front row seat, as an expert witness in shareholder litigation, to the devastating consequences for families who have overlooked the human and family element of estate and ownership planning.

Here are my biggest estate planning takeaways from two decades of experience:

  1. Values and priorities must be clear from the start.
  2. Only one person can be CEO.
  3. The plan cannot be kept secret.

Values and Priorities

The most effective estate plans I have seen are built on a foundation of clear values and priorities. The process starts with important questions like:

  1. What are your priorities for your wealth?
  2. What role do you want your wealth to play in your children’s future?
  3. What role do you want the business to play in your family’s future?
  4. What role do you want your family to play in your business’s future?

If your main priority is to fund philanthropy during and after your lifetime, your estate plan may look totally different than the family who needs to provide financial security for a special needs child. If you have adult children actively working in the business, your plan may consider different strategies than that of a family whose business is led by non-family executives.

Families with a mix of adult children in the business and other adult children who are thriving, or struggling, outside of the business face a whole other set of challenges.

The important thing is to make sure your estate and succession plan considers the priorities and realities of your family situation.

Only One Person Can Be CEO

Some of the most contentious family shareholder disputes I have witnessed were the result of estate plans that focused on tax planning without consideration of family dynamics. The biggest frequent mistake I have seen is giving equal control of the business to two or more kids. The track record of co-CEOs in business is dismal. Chances are, your family business success was established under the strong leadership of one person (maybe you, your parent, or grandparent). To continue to succeed, the business will need another capable leader, not a committee, and not equal partners. Sure, there are rare exceptions where shared leadership has succeeded, but why bet your family’s future against the odds?

Some families have a next-generation leader who clearly emerges. Other families may have no qualified members, or too many candidates to choose one. These are situations that may require a non-family CEO to step in for the next generation.

In my experience, the same principle is true for ownership. If ownership that had been concentrated with one person is then shared equally among siblings or cousins, conflicts will inevitably emerge. Without a controlling shareholder to settle disputes, litigation is often the only path.

The odds of success and family harmony are much better when everyone knows who is in charge.

The Plan Cannot Be Kept Secret

Family members, particularly adult children, need to know what the plan is for the family’s wealth and business so they can make informed decisions about their future. While a dramatic reading of the will makes for good cinema in the movies, in real life, this is a recipe for disaster.

The nightmare scenario is the family whose kids expected to base their careers and wealth on the family business, only to learn, as adults, that they will be left on their own. Too late to build their own independent wealth, shock, resentment, and a sense of loss can lead otherwise reasonable people to sue family members in a desperate attempt to recover the wealth they had expected. Stories like this are often behind the most contentious family estate litigation.

There should be no surprises when the time finally comes to transfer wealth and business ownership. In many cases, such transfers should be made during the parents’ lifetime under a schedule that has been communicated with the entire family.


Whether you are the founder of your business, or the steward of a multi-generational family business, many of the most important factors that will guide your ownership and wealth planning have nothing to do with money, tax, or business, and everything to do with family. Give these family considerations at least as much attention as you give the tax and other technical factors in your estate planning.