By Hilla Talati and Henri-Lee Stalk, J.D., Ph.D.
You carry meaningful responsibility within the family enterprise, even as the influence and guidance of the older generation continues to shape the path forward. As part of the “Now Generation,” you’re stepping into leadership at the intersection of tradition and change, navigating complex dynamics while helping shape the future of your family business.
Leading a family business can be incredibly rewarding, but it also comes with unique challenges that arise from owning assets together as a family. Your family needs to stay connected across generations, live out its values, revisit its mission regularly, and build both business skills and resilience to ensure continuity and maintain family control over time. Increasingly, it’s your generation that’s called on to lead by example in these efforts.
At the same time, decision-making in a family business can be slowed down by the need for consensus, the desire to maintain family harmony, reluctance to move beyond the founder’s original approach, or uncertainty about what future leadership will look like.
What’s often overlooked is that succession isn’t an event; it’s a process. Successful transitions require time, structure, and a genuine commitment to developing the necessary skills. For many families, this process unfolds over 15 to 20 years.
Without a clear plan for succession, it’s easy to feel unsure about how to grow and move forward. Whether you’re in a senior role or not, it can be frustrating when your family system lacks urgency or clarity around leadership development.
What can you do independently to build your capabilities and prepare for leadership?
Every family is different, but the stories that follow highlight the real challenges faced by Now Gen leaders and the practical strategies they’ve used to navigate transitions, manage family dynamics, and help move their businesses ahead.
Alex’s journey in leading a team of siblings while taking over from his father
Alex let out a sigh. It had been a long day. At 40, he’d been named the designated successor to his father as CEO just a year earlier, even though he was the third of four siblings, all of whom held executive roles in the business. He had worked side by side with his father over the past fifteen years to help build the company. His siblings agreed that Alex had played a critical role in attracting new customers and strengthening both the family and business brand. Still, there were days when it felt like nothing he did was good enough in his father’s eyes.
Earlier that day, he’d clashed with his older sister, who headed production, about whether to prioritize certain rush orders for key customers. And he’d also had a tense conversation with another sibling about bringing their son in as a post-college intern. That discussion was tricky, partly because his nephew’s behavior didn’t always reflect the family’s values, and partly because there was no formal internship program in place. That meant yet another responsibility would fall to Alex.
He knew he was still figuring out his leadership style and that his father’s top-down approach, focused on spotting mistakes, wouldn’t work with a team of siblings. He also found it difficult to manage his father’s emotional attachment to the business and fear of becoming irrelevant. This made it hard to have open conversations about the areas Alex needed to develop in to truly earn his father’s confidence as CEO. At times, Alex wondered: Is this really worth it? Would I be better off doing something on my own?
Realizing he needed guidance and a confidential sounding board, Alex turned to a leadership coach to help him work through the challenges he was facing.
Together, they identified key skills Alex could strengthen to collaborate more effectively with his siblings and his father and the steps he could take to manage the complex dynamics of the growing family enterprise.
1. Developing a servant leadership style
Alex decided to focus on being a servant leader by spending more time really listening to his siblings and understanding what they needed to succeed as leaders in the business. He made a point to recognize their efforts and ask for their input on problems, even on things outside their usual roles. Together, they created a Sibling Working Group that met every two weeks to talk about future ownership and business issues, both strategic and operational. By working through challenges together and being open to and prioritizing different ideas, Alex helped build a stronger sense of ownership and teamwork among them. Over time, his siblings started to see him less as a boss giving orders and more as a trusted partner managing the business with them.
2. Building an Empathetic and Collaborative Partnership with the Senior Generation
Alex realized he didn’t, and wasn’t expected to, have all the answers. But he still found it hard when his father often pointed out what wasn’t working or needed fixing, frequently reminding him that mistakes could put his retirement and the family’s financial security at risk. Over time, Alex understood that his father’s criticisms came from deeper fears: worries about whether Alex and his siblings could work well together, his own struggle to let go of control, and facing his own mortality. This understanding helped Alex respond with more empathy when his father criticized him. Wanting to build a stronger partnership, Alex changed his approach to focus on understanding his father’s motivations, fears, and hopes, instead of brushing off concerns or rushing to fix things. He started having regular informal breakfasts with his father to keep conversations going, rather than waiting for formal meetings. Alex also made a point to recognize and respect the legacy his father had built before suggesting any big changes. By involving his father in important decisions, they were able to agree on when decisions would be made together and when Alex and his siblings could make their own choices, learning from both successes and mistakes along the way. In addition, Alex and his family began working on a shareholder agreement to clearly outline how ownership would transfer between generations and to protect the financial interests of the senior family members who had invested in the business.
3. Investing in His and Others’ Learning
While talking with his coach about how the business and his role had changed over time, Alex realized he had never had any formal education related to his position or the wider business world. Since he had jumped in early to help his father build the company from scratch, most of his learning came from on-the-job experience. While valuable, this hands-on learning left gaps in his understanding of business operations and best practices, gaps he knew he and his siblings shared. Alex also wished he had a larger network of peers to turn to when facing tough business challenges. Reflecting on this, he saw a chance to support the next generation. For example, his nephew could really benefit from structured guidance to fit into the company culture and develop skills needed for long-term success in the family business. With his coach, Alex explored part-time, flexible learning programs that would help him improve his business skills and grow his professional network while still handling his busy job. He also asked trusted family executives to help design a structured internship for his nephew. This involved talking directly with his nephew to understand his interests, set personal development goals, and identify key behaviors that would show progress. To support his nephew further, Alex assigned him a mentor within the company, a senior family member who could coach him during the internship, and help him adjust to the company culture. Alex also worked with his siblings to figure out what areas they wanted to focus on for their own learning and growth, knowing that expanding their knowledge would not only boost their confidence but also make the family business more competitive overall.
4. Creating a Family Community and Ensuring Every Family Member Matters
The family had grown to ten third-generation members who, over time, would enter a business world very different from that of Alex and his father. With advice from his coach and input from his siblings and their spouses, Alex helped the family focus on building stronger connections across the different branches by starting monthly informal dinners. These gatherings gave the next generation a chance to build relationships, better understand their shared values, and learn more about the family business legacy. They also gave Alex’s nephew time to connect with his younger cousins and share what he was learning. Input from spouses and third-generation members helped the family rethink their approach to employee wellness, environmental sustainability, and philanthropy. These areas were important to the family as a whole, but were often overlooked amid the daily demands of running the company.
Aisha’s journey in shaping the future with her cousins
Aisha, recently turned 50, had led a family business division for ten years alongside two cousins. Although her father and uncles had stepped back from daily operations, they remained involved by attending the office and executive meetings. Their presence often limited open discussions, and major decisions still required their approval, slowing the second generation’s development as a cohesive leadership team.
While Aisha’s division performed well, she was concerned about the cousin’s struggling division facing rising input costs, price increases, customer loss, and unfavorable regulations. She questioned whether the family should continue investing in that business line. When Aisha raised her concerns with her father, he was reluctant to challenge his brother, who had built that division, fearing it would create discord between branches. The senior generation had maintained peace by keeping businesses siloed and avoiding interference. Without clear structures to address such issues, leadership remained unclear, leaving Aisha uncertain about how to proceed.
To navigate these challenges, Aisha decided to take a purposeful approach, implementing several key strategies to foster open communication, strengthen governance, and drive informed decision-making within the family business and across generations.
5. Modelling Direct Communication Across Family Members
Aisha knew that, eventually, she and her cousins would be running the family business without the senior generation’s guidance, and that building trust and growing the business would be difficult if they didn’t communicate openly. Even though her father had some reservations, Aisha chose to be upfront about the “Now Generation’s” concerns. She calmly shared the facts about the division’s performance and listened carefully to her cousins’ views. They all agreed they were worried about the underperforming division and felt these issues needed to be raised with the senior generation upfront. Aisha also learned that her cousin running that division was anxious about how things were going but didn’t know how to bring it up with her father. Together, the cousins acknowledged these concerns, reaffirmed their commitment to the business and to supporting each other, and agreed to develop a clear plan to raise the issue constructively with the senior generation.
6. Establishing Collaborative Governance for Now Gen
The three cousins began holding informal monthly dinners to openly discuss their businesses, challenges, and concerns. Over time, these gatherings helped them build the confidence and unity needed to collaborate effectively on a portfolio review, allowing them to jointly decide where to focus investments and efforts going forward. Occasionally, they invited family members not actively involved in the business to ensure the review addressed any overlooked questions relevant to the ownership group and to test their proposed approach to managing the division’s challenges ahead of their presentation to the senior generation.
7. Presenting Data-Driven Analysis to Mitigate Fear of Conflict
To encourage open and honest discussions, Aisha and her cousins put together a fact-based analysis of market trends, customer behavior, and regulations. They held a portfolio review meeting to help ease the senior generation’s fears of conflict and avoidance, creating a space for constructive, forward-looking talks. This helped the family make clear and transparent decisions about the business unit. Aisha’s father and uncles supported their efforts and were glad to see the cousins working together. Although the family is still careful about final decisions, they now have a clear, objective way to evaluate how investments impact the division. Through this process, Aisha and her cousins have built positive momentum in openly tackling the challenges facing their family business. They’ve strengthened their relationships and are starting to change how their family communicates.
Succession in family businesses is a long and often challenging journey that takes time, clear communication, and ongoing leadership development across generations. As part of the “Now Generation,” you’re balancing the legacy of the senior generation with the need to bring fresh ideas and greater transparency to meet changing business demands. It’s not always an easy path, it requires resilience, support from those around you, and attention to your own well-being.
When you’re unsure of your next steps, focus on three things: keeping conversations open among family members, encouraging collaborative decision-making across generations and with trusted non-family advisors, and deliberately investing in your own growth as well as that of your family. These efforts help strengthen family relationships and support the business’s long-term success. With patience and steady commitment, your generation can step into leadership with confidence and carry the family legacy forward.
Ultimately, moving from the “Now Generation” to senior leadership means taking ownership of your development. Growth isn’t always comfortable, but that discomfort often signals real progress. Succession isn’t something that just happens to you, it’s something your generation plans and builds together. The more intentional you are about how you grow, communicate, and lead together, the stronger and more confident your leadership will become.
