BY Jane Warner Senior Wealth Planning Strategist,
Bank of the West

Feb 22nd 2023

Financial PerspectivesInvestment

Why Can’t We All Just Get Along? How to Overcome Family Dynamics in Legacy Planning

Feb 22nd 2023

In the final stages of what seemed like a successful legacy planning process for a large family business, I learned something surprising: Nobody was happy with it. It was baffling. We’d addressed all the financial issues involved, but no one liked the proposed solutions. After some in-depth discussions about family dynamics, we figured it out.

They were never going to agree on an outcome: Two people involved were not getting along and that was creating a roadblock to agreement.

For family businesses, what’s personal is also business, and what’s business also gets personal. And given all the sensitive issues that can come up during legacy planning—which is estate planning that includes your financial and non-financial goals for your family and business—it’s no wonder I see difficult situations all the time in my work advising families on the process.

For family businesses, what’s personal is also business, and what’s business also gets personal.

The business is often a family’s biggest asset, so how it could evolve (or resist evolving) when leadership changes is already a contentious conversation. New leaders always bring new values, philosophies, and ideas with them. Throw complicated family dynamics into the mix, and it’s easy to see why only a third1 of US family businesses have managed to get a proper succession plan in place.

Your family can defy those odds. By being proactive about resolving family conflicts and improving communication, business-owning families can set themselves—and their business—up for success with a strong, clear legacy plan.

Here are a few key strategies to keep in mind:

5 Strategies for Overcoming Conflict in a Legacy Planning

  1. Stop Dragging Your Feet

    Think you’ve got plenty of time left before you need to start your business succession plan? Your kids likely disagree. Nearly six in 10 next-gen leaders say that the current generation’s hesitance to retire is a problem, according to PWC.2 And if they’re feeling anxious and unprepared, you’re putting your legacy at risk. Research shows 25 percent3 of failed family business transitions happen because of an ill-prepared heir.

    Ideally, your legacy plan will be in place well before it is implemented—whether that is months or years in advance depends on a lot of factors. Many families I work with only put off these discussions because they know they’re going to involve disagreements. And who wants to argue with family? But even if it won’t go into effect for five or 10 years, starting your legacy plan now gives both generations more time to address potential issues and get on board.

    Plus, an early start will become invaluable if an illness, injury—or just the sudden urge for an extended vacation—prompts an unexpectedly early transition.

  2. Start with Values, Not Vested Interests

    Before asking, “Who’s going to be the boss?” ask, “What are we about?” It’s easy to assume that everyone shares the same ideas about company culture and values in a family business. But you can avoid other misassumptions down the road by making sure you’re all starting with the same idea of what your business is all about. A 2021 survey4 found family businesses with written values were better prepared for succession than those without.

  1. Relearn How to Listen

    Start getting down to business—by brushing up on your active listening skills. Fewer than one in three business-owning families5 say that their family’s listening skills are good, and just over a quarter rate them as average. The reasons they tend to talk past each other are as obvious as they are hard to shake: Older generations believe that they know best based on decades of experience; younger generations believe they know better based on today’s markets and future-facing ideas. Often, they’re both partly right.

    Don’t hesitate to bring in a conversation facilitator6 to help with tricky topics and ensure everyone is heard. It’s not a judgment on your family closeness. It’s a sign of love and respect that you want to keep things civil, fair, and well-communicated.

    Another strategy to try: round table, a discussion method that encourages active listening. Everyone at the table is given a specific amount of time to express themselves, and no one else speaks during that time.

  1. Bond Over Giving Back

    Your legacy plan will cover more than just your business, which is an opportunity to find common ground. Philanthropy can be a shared goal across generations, even if they feel passionate about different causes or charities. A Blackbaud study7 found that Baby Boomers like giving to local social services organizations and religious institutions, while Gen Z prioritized giving to benefit children and animals. Get involved in intergenerational compromise by finding ways to agree on how to give.

    Does the long-running family foundation feel more like a hassle than a privilege for the younger generation? Giving in a different way, like through a donor-advised fund, could allow your family to move forward with multiple giving priorities and less time commitment. This type of win-win can help both generations realize consensus is possible and motivate everyone to bring the same open-mindedness to the business succession planning table.

  1. Lean into Letting Go

    A family business I once worked with had some of the traditional dynamics we’ve been talking about: The dad and founder of a manufacturing company was hesitant to let go of the old way of doing things. The son had a big idea to innovate. Ultimately, the son was given some latitude to invest in his vision—and grew the company 24 times its original size.

    Now, I know that isn’t going to happen every time. Sometimes, the next generation is going to fail. But experts tell us that the way to build resilience in the next generation of family business owners is to give them room to fail.8

    To a parent and someone who spent their life building a business they love, it can sound like utter madness. But then, when I ask a founder to tell me some of the biggest lessons they learned over the course of growing their business, so many stories are about risks, failures, and near misses. Understanding how valuable those learning experiences were for them helps leaders realize how important it is to give the next generation the chance to learn by doing as well.

When entering tough legacy planning conversations, keep in mind that the transition is going to happen no matter what—with the conflict behind you or unresolved.

When developing a legacy plan, both generations are generally happier in the end when compromise drives the process. For the younger generation, this means accepting institutional wisdom. For the older generation, it means letting go of the instinct to micromanage.

When entering tough legacy planning conversations, keep in mind that the transition is going to happen no matter what—with the conflict behind you or unresolved. Everyone can agree the former is best. Most clients I work with feel grateful to have spent their lives running a family business. That’s why it’s so sad to know that many family businesses don’t survive past the second or third generation.

Doing the work of legacy planning isn’t easy, but if you’re thinking of exploring your options, a good place to begin is to reach out to a wealth advisor to learn more or start the process.

Author image

Jane Warner Senior Wealth Planning Strategist,
Bank of the West

Jane Warner has over 15 years of experience working with high and ultra high-net-worth individuals and families on the wealth planning process. She's also a specialist in business succession, estate plan coordination, and family dynamics solutions. Jane has spoken at events across the country on wealth transfer and business planning.

Footnotes small arrow indicator

1. PwC, “2021 Family Business Survey: US Findings,”

2. PwC, “PwC’s Global NextGen Survey 2022,” March, 2022,

3. Journal of Business Venturing, “Correlates of success in family business transitions,” September 1997,

4. PwC, ” 2021 Global Family Business Survey,”

5. Family Enterprise Foundation, “Alchemy and the Family Enterprise,” June 2022,

6. Harvard Business Review, “Avoiding Conflict Will Only Hurt Your Family Business,” October 2022,

7. Blackbaud, “The Next Generation of American Giving,” April, 2018,

8. Harvard Business Review, “How Parents Can Promote Resilience in the Family Business,” October 2022,

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