In our recent CEO Roundtable on January 27, 2026, we brought together business leaders from diverse industries to discuss one ofthe most challenging aspects of organizational leadership: navigating generational transitions while preserving company culture. The conversation revealed powerful insights that speak directly to the heart of what CultureWise helps organizations achieve - building intentional cultures that transcend individual leaders and sustain themselves across generations.
One participant, leading a fifth-generation auto group in its 112th year of operation, shared a soberin greality that resonates throughout family business literature: the first generation creates it, the second generation grows it, and the third generation often destroys it. This pattern isn't inevitable - it's a symptom of missing systems.
The difference between businesses that thrive across generations and those that falter comes down to one critical factor: whether culture is person-dependent or system-dependent. When culture lives solely in the founder's head or the current leader's personality, it becomes fragile. When it's embedded in shared practices, common language, and repeatable behaviors - exactly what CultureWise fundamentals provide - it becomes resilient.
Multiple roundtable participants emphasized a crucial requirement for next-generation family members: they must work outside the business for a minimum of two to five years before returning in leadership roles. This isn't just about gaining experience- it's about earning credibility.
As this leader explained, their company requires family members to start in base-level roles within the business first, then leave to work for competitors, establishing their own network and proving themselves independently. Another participant from a global logistics company echoed this approach, noting that all owners' children must start outside the business and work their way up from warehouses or truck yards.
This practice demonstrates a fundamental CultureWise principle: Speaking Straight. When family members earn their position rather than inheriting it, the organization can practice honest, direct communication about performance and fit. The alternative - nepotism without credibility - creates an environment where people can't speak truthfully, breeding resentment and undermining the very culture the family wants to preserve.
Perhaps the most powerful theme that emerged was the willingness of successful multi-generational businesses to question the assumption that family members should automatically lead. As one logistics company president stated plainly, he doesn't see his company going to third-generation family ownership unless someone proves themselves to be the best qualified leader.
This leader explained his perspective on serving the 500 families that depend on his company. This shifts the question from asking if a family member is good enough to asking who is the best person to lead the company into the future.
One participant shared his company's difficult but ultimately rewarding journey of recognizing that the oldest sibling, despite being a natural choice by birth order, wasn't the right fit for the CEO role. When they made the tough decision to realign roles based on strengths rather than age or tradition, both the business and the family relationships improved.
This exemplifies another CultureWise fundamental: Getting Clear on Expectations. When roles, responsibilities, and decision rights are clearly defined - separate from family hierarchy - everyone can operate with confidence and clarity.
One participant's story powerfully illustrated the cost of avoiding difficult conversations. After working for 30 years in a family business where the owner was dying of cancer, this leader found herself trying to negotiate a purchase agreement with nephews she had no relationship with while the owner avoided business discussions. The uncertainty nearly caused her to retire rather than continue in limbo.
Now, as the owner of that business, this leader has taken the opposite approach. Though she's ten years from retirement, she's already identified her successor, communicated the plan to all senior leaders, and is actively preparing her replacement by having him attend every significant business meeting - from bank meetings to insurance renewals.
As this leader noted, you can never train early enough. More importantly, she's providing her team with security about the future, ensuring they don't face the uncertainty she experienced.
This approach embodies multiple CultureWise fundamentals working together: Listening Generously to understand what employees need to feel secure, Speaking Straight about succession plans rather than hoping everything works out, and Practicing Accountability by taking concrete steps today to prevent future problems.
One logistics company president raised a challenge that resonates deeply with family businesses and entrepreneurial companies alike: what to do about people who helped build the company but can no longer perform at the level required as the business scales.
This leader explained the dual responsibility leaders face - loyalty to those who helped build the company, balanced against responsibility to all current team members who deserve the best version of the organization.
Another leader described his company's painful but necessary journey over the past two years, moving from viewing their many 20-, 25-, and 30-plus-year employees as a badge of honor to recognizing that some weren't in the right seat or shouldn't be on the bus. With dignity and support, they made changes that ultimately benefited everyone.
This leader reflected on the process, noting that while it was difficult, their only regret was not doing it sooner.
This situation demands Blameless Problem Solving - the ability to address performance gaps without making it personal or assigning fault. These employees served well in their season. The company has changed. Both truths can coexist. The key is handling transitions with respect, support, and clear communication about how the company can honor their contributions without compromising everyone else's future.
One CEO shared how his company implemented the Entrepreneurial Operating System (EOS) to create what he called a people operating system - formal structures for everything from 10-year vision to accountability charts to individual scorecards. Another participant described using third-party coaches to help navigate sibling dynamics and role assignments.
The common thread in these approaches is the recognition that sustainable culture cannot depend on any single person's judgment or personality. One president emphasized the critical importance of scalable systems, noting that what works informally at 71 employees won't work as the company grows.
A Director of People and Culture, just three weeks into her role at a construction company, observed that without standardization, organizations risk spending more time on administrative tasks rather than serving clients, customers, and employees effectively.
This is precisely where CultureWise fits into the transition challenge. The fundamentals provide a common language and shared behavioral expectations that transcend individual leaders. When Listening Generously, Speaking Straight, Getting Clear on Expectations, Practicing Accountability, and Practicing Blameless Problem Solving become the way everyone in the organization operates - not just the founder's personal style -culture becomes transferable.
An interesting tension emerged around employee communication about succession. One non-family CEO navigating a family business's transition reported getting asked frequently about what happens when he leaves. Another leader noted that her open communication style, including implementing town halls, created more awareness of succession concerns than existed before.
A People and Culture leader made a crucial observation from her corporate background: people want to know, and when they don't know, they speculate. These speculations turn into rumors that can chip away at culture as people get creative with their theories.
The balance lies not in sharing every detail of succession planning, but in providing enough transparency that people feel secure. As one leader demonstrated, communicating clear plans - even when they're years away from execution - prevents the destructive speculation that can undermine culture.
This requires Speaking Straight about what you know, what you don't know, and what you're working on - treating employees as adults who can handle nuanced information rather than children who need protection from uncertainty.
A powerful moment in the conversation came when the facilitator, David Friedman, shared a memory from his own family business. As the fourth of five siblings but the CEO of the company, he realized he was holding back in his leadership because he didn't want his oldest brother to feel bad. Meanwhile, his brother - who was better suited as a number two than a number one - was trying to be more of a number one because he felt he should as the oldest.
When they gave each other permission to play the roles best suited to their strengths, David explained, it freed them up and unlocked significant potential in the company.
One president described a similar approach with her team: sitting back and giving people permission to not know everything, emphasizing that she doesn't expect omniscience from her leaders.
This concept of permission - to not be everything, to not know everything, to play to your strengths rather than fitting a predetermined mold - creates psychological safety. It's the environment where Listening Generously and Speaking Straight can flourish, because people aren't performing roles that don't fit them while pretending everything is fine.
One participant introduced perhaps the most colorful metaphor of the conversation: pigeon management -when the exiting founder swoops in, struts around, craps on everything, and flies away. His challenge is finding specific projects where his father still feels valuable and adds value without directly negatively impacting the team he is now managing.
This leader noted that this transition has taken a decade, but they've reached a point where he needs to help his father slow down without removing his sense of purpose.
This graceful transition requires extraordinary emotional intelligence from all parties. It demands that the next generation Listen Generously to understand the founder's need for continued purpose and contribution. It requires the founder to Get Clear on Expectations about what role they now play. And it necessitates that everyone Practice Accountability to agreed-upon boundaries, even when emotions run high.
Multiple participants emphasized the critical role of third-party facilitators, coaches, and systems in successful transitions. One finance director noted that people often believe outside facilitators more readily than internal voices, even when the internal voice has the same expertise.
One participant shared a humorous but telling anecdote: one of their coaches quit on his brother, declaring him uncoachable. Yet this same brother - described as the best person you could meet as a friend - simply had a different working style that required external structure to navigate productively.
One logistics president captured the necessity of outside input succinctly: there's no way to be the best at what you do if you just live in a tiny bubble thinking that bubble will make you the best version of yourself.
This is why CultureWise works -it provides an external framework with language and practices that help people have conversations they couldn't have otherwise. It gives permission to Speak Straight because you're not creating your own rules; you're following a shared system that applies to everyone equally.
One CEO articulated a challenge echoed across the group: finding the next generation of leaders who want both the rewards and the responsibility. This leader described people who want the engineering expertise and financial success without the burden of leadership, even though he knows they're capable.
Another leader offered a practical approach: when she spots potential leaders getting into firefighting mode or carrying too much burden, she asks a simple question - how do we do this when you're not here? Her focus on cross-training prevents people from becoming indispensable firefighters rather than developing systems that can run without them.
One company founder acknowledged his own limitations candidly: as a sales guy rather than a CEO by trade, he recognizes he could benefit from someone with better skills in certain areas of running the company.
This self-awareness - knowing what you don't know and being willing to bring in people better than yourself - is crucial for sustainable growth. It requires Practicing Accountability to the organization's needs rather than to ego, and Speaking Straight about gaps in leadership capacity.
When asked about their biggest leadership transition challenges, the responses varied in specifics but shared a common theme:
One leader worried about whether her successor can hire the right support. Another focused on ensuring value system alignment when inevitable challenges arise. A third emphasized having tough conversations with people who can't scale to the next level. One highlighted the need to build bench strength. As one CEO summed it up: it all comes down to people.
A People and Culture Director zeroed in on culture: maintaining the culture that the team has worked hard to build over the years while taking what the founders created and evolving it in the right ways.
This is the heart of the matter. Leadership transitions aren't primarily about financial structures or legal documents. They're about people - their relationships, their capabilities, their fears, their aspirations, and the culture that binds them together or fails to.
What emerged from this roundtable is a clear picture of why intentional culture work matters so much in leadership transitions. When culture is:
Named and defined through clear fundamentals rather than implicit in the founder's personality
Practiced daily and reinforcement rather than hoped for
Applied universally to everyone from the CEO to the newest hire
Used as a decision-making framework for tough choices about roles, performance, and succession
...then it becomes the stable foundation that allows leadership transitions to succeed.
CultureWise provides the common language that one CEO sought through EOS, the communication framework that another leader is using to prepare her successor, the behavioral standards that allow difficult conversations about scaling, and the cultural continuity that organizations are working to preserve through transitions.
When everyone in the organization knows what it means to Listen Generously, they can hear difficult feedback about succession readiness. When Speaking Straight is the norm, conversations about who's ready and who's not become possible. When Getting Clear on Expectations is standard practice, role confusion between generations dissolves. When Practicing Accountability is built in, both founders and successors can hold themselves and each other to transition commitments. And when Practicing Blameless Problem Solving is the approach, difficult decisions about legacy employees or family member fit become about finding the right solution rather than assigning blame.
If you're navigating a leadership transition - whether imminent or years away - the insights from this roundtable point to clear action steps:
Start earlier than feels necessary. As one leader demonstrated, beginning succession planning ten years before retirement isn't too early - it's wise.
Require credibility, not just capability. Next-generation leaders must earn their position through outside experience and internal performance, not family connection alone.
Ask the right question. Not is this person good, but who is the best person to lead this company into the future.
Have the hard conversations now. Avoiding difficult discussions about fit, performance, or role creates problems that compound over time.
Build systems, not dependencies. Whether through EOS, coaching, or CultureWise fundamentals, create structures that outlast individual leaders.
Communicate transparently. People deserve enough information to feel secure about the future, even when details aren't final.
Honor legacy without being bound by it. Respect what founders built while making decisions based on what the current and future organization needs.
Seek outside perspective.Whether coaches, peer groups, or cultural frameworks, external input breaks through the limitations of internal perspective.
Most importantly, recognize that successful transitions don't happen by accident. They require intentional effort, difficult conversations, clear systems, and a culture strong enough tocarry the organization from one generation to the next.
This is exactly what CultureWise provides: a proven framework for building that kind of culture. Not a culture that depends on any single leader's personality or presence, but one that lives in shared practices, common language, and daily behaviors that anyone can learn and everyone can practice.
As these CEOs demonstrated, the businesses that successfully navigate generational transitions are those that invest in culture as intentionally as they invest in strategy, systems, and succession planning. Because in the end, culture is what connects all three.
If the challenges discussed in this roundtable resonate with you - whether you're planning a leadership transition, struggling with generational dynamics, or simply want to ensure your culture outlasts your tenure - CultureWise can help.
Our proven framework gives you the tools to create a culture that isn't dependent on any single leader's personality. Instead, you'll build shared practices, common language, and daily behaviors that anyone can learn and everyone can practice.
Don't wait for a crisis to start planning. Don't let your culture remain implicit and fragile. Take the first step toward building a culture by design - one that will carry your organization successfully from one generation to the next.
Contact CultureWise today to learn how we can help you transform your culture from person-dependent to system-dependent, ensuring your legacy lives on through intentional, transferable practices.
About This Roundtable
This CEO Roundtable brought together leaders from diverse industries including automotive, logistics, construction, manufacturing, staffing, and real estate development. Participants ranged from second-generation family businesses to fifth-generation enterprises, from companies with 25 employees to those with 500, providing a rich cross-sectionof perspectives on the universal challenges of leadership transition andculture preservation.