In this episode of Open For Business, hosts Stuart Brown and Norman Kallen talk with organizational psychologist, entrepreneur and family business advisor Lisë Stewart about why succession planning involves far more than choosing the next leader. Drawing on nearly four decades of experience, Lisë explores how communication, governance, leadership development and family dynamics can shape the long-term success of a family business.

Through real-world case studies, she discusses how business owners can prepare the next generation, navigate difficult family conversations and determine the right path forward, whether that means family leadership, professional management, an ESOP or a sale. The conversation offers practical guidance for owners looking to protect both the business and family relationships across generations.

Key Points From This Episode:

[00:00:00] Introduction.

[00:01:04] Stuart introduces Lisë Stewart and her background in organizational psychology, strategic planning, training, and human performance management.

[00:02:24] Lisë discusses returning from sailing in the Caribbean and how she continued working with family businesses while away.

[00:05:29] Why Lisë combines face-to-face and virtual meetings when working with clients.

[00:07:13] The complexity of family businesses and why consultants need to be comfortable with ambiguity and conflict.

[00:08:27] Using “authentic curiosity,” compassion, and powerful questions to build trust with clients.

[00:10:01] Starting with “shallow entry” questions before moving into more emotionally charged family discussions.

[00:12:10] Lessons Lisë learned from starting nine businesses and viewing failure as a learning experience.

[00:14:33] Why succession and exit planning can begin as early as the startup stage.

[00:17:41] How unresolved family issues can distract leaders from what the business actually needs.

[00:20:30] Understanding the difference between genuine entitlement and the fear of living in a successful parent’s shadow.

[00:23:55] The Doyle family’s structured approach to preparing family members for leadership.

[00:26:16] The Fletcher family’s succession risks and the consequences of failing to develop future leaders.

[00:28:14] How the Doyle family created clear boundaries between the retiring father and the next-generation CEO.

[00:28:59] Why advisory boards can be a cost-effective source of outside knowledge and expertise.

[00:32:02] Selecting effective advisory board members, setting term limits, and keeping boards focused on strategy.

[00:34:14] Comparing the Doyle family’s strategic board with the Fletcher family’s ineffective “old boys network.”

[00:37:06] What Lisë believes could happen to the Fletcher business if its current leader suddenly passed away.

[00:38:17] Why succession planning should focus on the long-term success of the business rather than simply naming one successor.

[00:42:23] Alternatives when the next generation does not want or is not prepared to run the family business.

[00:43:34] Helping a family recognize when passing the business to a child could set that child up to fail.

[00:46:49] How the Doyle family addressed compensation, ownership distributions, reinvestment, and expectations before conflict emerged.

[00:50:52] Lisë’s central lesson: deal with emotional issues before emotion becomes the issue.

[00:52:15] Why difficult family conversations may benefit from an experienced professional facilitator.

[00:53:25] Lisë emphasizes that it is never too late to begin addressing succession and family business challenges.

Links:

Lisë Stewart on LinkedIn: https://www.linkedin.com/in/lise-stewart-00bb9b2/

Open for Business show notes, past episodes, and featured resources: stevenslee.com/Open-for-Business

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

Running a business means navigating change, making difficult decisions and constantly looking ahead. Whether you are growing your company, preparing for a transition or planning your next chapter, Open for Business examines the business and personal issues that come with ownership.

Hosted by Stuart Brown and Norman Kallen (business advisors who happen to be attorneys), the podcast features discussions with entrepreneurs, executives, authors and advisors on leadership, company culture, succession planning, private equity, wealth management and more.

In this episode of Open For Business, hosts Stuart Brown and Norman Kallen speak with Bill Wilson, founder of Wilson Creek Winery in Temecula, California, about building and leading a successful multigenerational family business.

Bill shares how an early career setback in finance ultimately led to an unexpected opportunity to purchase land in Southern California’s Temecula wine region with his parents and siblings. He discusses the challenges and rewards of working alongside family members, sharing lessons learned from decades of growing a business together. He highlights the importance of bringing in trusted consultants and advisors who can provide objective, expert guidance when personal relationships make it difficult to maintain a neutral perspective.

Bill also reflects on his family's entrepreneurial journey, the sacrifices required to grow their business, and the values that have helped them navigate change while preserving both the company and the family relationships behind it.