Every family business carries history. It shows up in the stories of how the business began, in the way decisions are made, and in the expectations passed from one generation to the next.
Handled well, that history can be a powerful force. It provides a foundation of values, identity and resilience that gives the business strength. But it can also feel heavy. When the past overshadows the need to adapt, history risks becoming a burden rather than a source of advantage.
When history helps and when it holds you back
At TWYD we see both sides. Pride in tradition and continuity can give families cohesion and purpose across generations. It offers a sense of belonging that is difficult to replicate in non-family businesses. The business becomes more than a place of work: it is part of the family’s identity, rooted in memory, values and shared experience.
Yet history can also create constraints. Emotional ties to “how things were done in the past” can limit the willingness to explore new opportunities. Leadership may stay in place longer than is healthy because of loyalty to past contributions. A family’s attachment to a name, a product or a way of operating can sometimes cloud objectivity at precisely the moment when clear decisions are needed.
This is not about choosing between tradition and progress. It is about recognising when history is helping to propel the business forward, and when it is quietly holding it back.
Learning from defining moments
Every family business has defining moments that become part of its story. These may be triumphs, weathering an economic downturn, securing a transformative contract, passing the reins successfully to a new generation. They may also be struggles, missed opportunities, conflicts between family members, or an appointment that did not work out.
These moments matter because they form the lens through which future decisions are judged. A family that remembers the risk of over-expansion a generation ago may be overly cautious today. A family that recalls a bold diversification that paid off may be more willing to take a chance again.
The challenge is that history is not neutral. It is retold, reinterpreted and reshaped over time. What one generation sees as a proud achievement, another may see as an outdated story. What one group recalls as a painful misstep, another may barely remember. That is why history cannot be treated simply as fact. It is a living narrative that shapes attitudes, trust and decision-making.
The role of storytelling
Storytelling is one of the most effective ways to keep history constructive. Done well, it passes on values, builds belonging and connects the rising generation to the family’s purpose. Stories of resilience – a founder taking risks to secure the future, or a family uniting to protect jobs during a crisis can inspire commitment for decades.
But stories can also trap. “We’ve always done it this way” is rarely the beginning of innovation. Old conflicts, if continually rehearsed in family stories, can fester and limit trust. Even stories of success can become obstacles if they stop a family recognising that a new context requires a new approach.
Families that thrive over generations tend to be those that take control of their own story acknowledging the past but also being deliberate about how it is told and what it means for the future.
Carrying history well
For many families, the real challenge is not whether history matters, but how it is carried. The past can steady a business or weigh it down. It can be a guide or a distraction. The difference lies in whether history is consciously recognised, reflected on and used as a source of strength, or left unmanaged to distort decisions and relationships.
At TWYD we see time and again that history is often the silent player in leadership moments. A succession plan derailed by unresolved conflicts from decades earlier. A board held back by stories of what happened to a previous generation when it tried to professionalise. A family struggling to bring in external executives because of unspoken comparisons to a long-serving leader from the past.
Making these dynamics visible is often the first step to moving forward.
A historian’s eye
This is where Oliver Denton, our Associate Partner, brings something different. Alongside his business expertise, Oliver is also a trained historian. He understands that history is not just a record of events, but a living force that shapes how families see themselves and their choices.
In practice this means asking families not only “what happened?” but also “how do you remember it?” and “what does it mean to you today?” Those questions can uncover assumptions, loyalties and fears that influence decisions more than financial data or strategy slides ever could.
Oliver’s dual perspective as both historian and advisor allows TWYD to guide families in carrying their history well, not as a burden, but as a source of clarity and confidence for the next chapter.