In the romantic narrative of entrepreneurship, the founder’s vision is sacrosanct—a guiding star that lights the way to success. It’s the story of Steve Jobs and Apple, Elon Musk and Tesla, Richard Branson and Virgin. These visionary leaders are celebrated not just for their business acumen but for the sheer force of their ideas, ideas that propelled their companies into the stratosphere. But what happens when that same vision, once the lifeblood of the business, becomes its ball and chain?

Welcome to the legacy dilemma, where the founder’s original vision, so pivotal in the early days, becomes the company’s burden. It’s a delicate dance between honouring the past and embracing the future, between staying true to what made the company great and evolving to meet new challenges. And as many businesses have discovered, it’s a dance that’s easy to stumble in.

The Weight of Legacy

Consider the cautionary tale of Kodak. For decades, Kodak was synonymous with photography. It was a brand built on the founder’s vision of making photography accessible to the masses—a vision that drove the company’s dominance in the film industry. But as the digital age dawned, Kodak found itself at a crossroads. The company had developed the first digital camera in the 1970s, but the vision of its founder, George Eastman, had become so deeply ingrained that the company couldn’t pivot. The fear of cannibalising its lucrative film business kept Kodak from fully embracing the digital revolution, and the rest, as they say, is history.

Kodak’s story isn’t unique. It’s a narrative that has played out in boardrooms around the world, where the founder’s vision, once the north star, becomes a set of golden handcuffs. The very principles that brought the company success become the barriers to its evolution. It’s the legacy dilemma in action, where the company’s past holds it hostage, preventing it from adapting to the future.

The Visionary Trap

The trouble with a founder’s vision is that it’s often both a blessing and a curse. On the one hand, it provides clarity and direction, rallying employees and stakeholders around a common goal. On the other hand, it can create blind spots, locking the company into a particular way of thinking, even when the market signals a need for change.

Let’s take a look at Yahoo, once a darling of the early internet era. Founded with the vision of being the go-to web portal, Yahoo became a giant in the dot-com boom. But as the internet evolved, so too did user behaviour. Search engines, social media, and mobile apps started to erode Yahoo’s relevance, yet the company clung to its original vision, attempting to be all things to all users. It was a strategy that led to bloated services, missed opportunities, and eventually, a diminished brand.

The lesson here is clear: a founder’s vision can be a powerful tool, but it can also become a trap. The very clarity that drives early success can become rigidity, preventing the company from seeing the broader picture, from recognising that sometimes, the best way to honour the founder’s legacy is to let it evolve.

When to Hold On and When to Let Go

So, how does a company navigate the legacy dilemma? The first step is recognising when the founder’s vision is no longer serving the business. This doesn’t mean abandoning the core values or mission, but rather reassessing how those principles are applied in a changing landscape.

One company that has managed this balance effectively is IBM. Founded in 1911, IBM was for decades synonymous with mainframe computers and hardware. But as the technology landscape shifted towards software and services, IBM faced the prospect of becoming obsolete. Instead of clinging to its hardware roots, IBM redefined itself, pivoting towards consulting and cloud services while still leveraging its expertise in computing. It was a bold move that allowed IBM to stay relevant while respecting its legacy.

The key to IBM’s success was its willingness to evolve, to reinterpret the founder’s vision in a way that resonated with modern needs. It’s a delicate balance—holding onto the essence of what made the company great while letting go of the aspects that no longer serve it.

The Role of Leadership

Navigating the legacy dilemma requires strong leadership, leaders who can honour the past while steering the company towards the future. This often means making tough decisions, challenging the status quo, and sometimes, going against the very principles that were once seen as sacred.

One example of such leadership is Satya Nadella at Microsoft. When Nadella took the helm in 2014, Microsoft was still largely driven by the vision of its co-founder, Bill Gates—a vision that prioritised Windows and Office above all else. But the market was shifting, and Nadella recognised that clinging to the old model would limit Microsoft’s growth. He shifted the company’s focus towards cloud computing, open-source software, and collaboration tools, effectively reinventing Microsoft for the modern era. The result? Microsoft is now one of the most valuable companies in the world, a testament to Nadella’s ability to evolve the founder’s vision without losing its core identity.

The Perils of Over-Adaptation

Of course, there’s a flip side to this dilemma—when companies swing too far in the opposite direction, abandoning their legacy entirely in the rush to innovate. This can lead to a loss of identity, alienating loyal customers and diluting the brand’s essence.

Take the case of Gap Inc., which in its quest to stay trendy and relevant, moved away from the classic, American-casual style that had originally defined the brand. In doing so, Gap lost touch with its core customers, and the brand has struggled to regain its footing ever since. It’s a stark reminder that while adaptation is crucial, it must be done thoughtfully, with an eye towards preserving the brand’s soul.

Embracing a Legacy with Flexibility

The solution to the legacy dilemma lies in finding a middle ground—one where the founder’s vision is respected but not worshipped, where the company’s core values serve as a foundation rather than a cage. This requires a culture of flexibility, where innovation is encouraged, and where questioning the status quo is seen as a strength, not a threat.

For companies grappling with this dilemma, the goal should be to embrace the legacy while allowing it to breathe, to evolve with the times. It’s about recognising that a strong legacy doesn’t mean rigidity, but rather a clear sense of identity that can adapt to new challenges and opportunities.

Conclusion: The Art of Balancing Legacy and Innovation

In the end, the legacy dilemma is about more than just business strategy; it’s about the tension between tradition and progress, between the past and the future. For companies, the challenge is to navigate this tension with wisdom and foresight, to honour the founder’s vision while recognising when it’s time to chart a new course.

It’s a delicate dance, one that requires both reverence and boldness, a willingness to look back with pride while forging ahead with courage. Because in the ever-changing world of business, the companies that thrive are not those that cling rigidly to their past, but those that use their legacy as a springboard to embrace the future.