BAH HUMBUG! Entrenched Leadership in Media's Digital Transformation

Summary: Even brilliant, seasoned execs can become barriers to digital transformation in streaming, TV, and film - not out of malice, but from a potent mix of success bias, fear of failure, and good old-fashioned institutional drag.

Through empathy and experimentation (think pilot programs, cross-generational teams, and well-aligned incentives), change agents can work with legacy leaders to phase in transformation without blowing everything up. This article includes Disney and Blockbuster as case studies.

What Is Entrenched Leadership?

In the context of business change, entrenched leadership refers to long-standing leaders who are deeply set in their ways and resistant to new approaches. These are the Old Guard executives who have often enjoyed success with traditional models and thus find it hard to pivot. Their leadership style and strategies become immovable fixtures in an organization’s culture. Entrenched leaders tend to stick to what worked in the past, even as the market evolves around them. In media companies, this often means clinging to legacy distribution channels and business models, even when new digital models emerge and prove successful in the general market.

Such leaders aren’t necessarily inept. In fact, many have admirable track records. But their long tenure and prior wins can create a confirmation bias: a belief that the old formula will continue to work. They may downplay disruptive innovations or see them as fads. In industries undergoing digital transformation, entrenched leadership becomes a double-edged sword: their experience is valuable, but their inertia can slow down adaptation.

Organizational debt (barriers to change) often encompasses entrenched leadership and structures perceived as immovable, creating cultural headwinds against change. In short, entrenched leadership is when leaders become stuck in the status quo, obstructing the very reinvention their companies need to survive in the digital age.

Root Causes of Entrenched Leadership

Why do capable executives become entrenched in the first place? There are several root causes:

• Past Success and Legacy Mindset: Ironically, success can breed complacency. If a network executive has dominated broadcast ratings for years, they might assume they can rely on the same strategy indefinitely. For example, Kodak’s leaders famously invented the digital camera but shelved it to protect their film business because they were entrenched in their own historical success and feared that embracing digital would cannibalize their core film sales. Their prior success blinded them to new tech, and clinging to a legacy model caused historic loss of their market share.

  
  

• Fear of Cannibalization and Risk: A huge barrier is the fear of cannibalization, defined here as the idea that a new digital product will undermine existing revenue. Leaders have worried that streaming will eat into cable profits, or online rentals will kill store rentals. In their caution, they chose to preserve the old (short-term safety) at the expense of the new (long-term growth). This “if it ain’t broke, don’t fix it” attitude comes from a place of risk-aversion. They have quarterly targets to hit and shareholders to satisfy, so sticking with the known path feels safer than betting on unproven innovations. This is a particularly sticky challenge when leaders have to educate their investors and risk losing their jobs before the transformation pays off.

  
  

• Organizational Culture and Siloes: Entrenched leadership often sits atop an equally entrenched hierarchy. Large media organizations can be bureaucratic, with siloed divisions and processes built around the old model. Leaders who rose through these ranks may have institutional inertia – the whole company culture reinforces doing things “the way we always have.” Over time, these leaders might view their procedures as gospel, making them less receptive to radical change. When an entire team is accustomed to one playbook, even (sometimes, especially) the leader finds it hard to break the norm.

  
  

• Lack of Digital Acumen: Some legacy media leaders simply don’t have the digital knowledge or talent around them. A film studio CEO who excelled at theatrical releases might not understand algorithms, streaming tech, or data-driven content strategy. This skill gap can lead to denial or dismissal of digital trends. It’s easier to label new tech as a hype or a niche you don’t need, rather than admit you don’t fully grasp it. (This was evident when Blockbuster’s leadership underestimated streaming and dismissed Netflix as a trivial competitor – they didn’t see the tech shift coming partly because it was outside their expertise.)

  
  

• Power and Politics: Longtime leaders often hold considerable sway and may feel threatened by change agents, whether internal digital teams or external consultants. Admitting the need for a new direction can be perceived as admitting their own approach was flawed. Middle managers might reinforce their bosses’ views to stay in favor. These politics create an echo chamber that reinforces the leader’s entrenched stance. It’s easier for everyone to agree “let’s not rock the boat” than to challenge a powerful CEO on a controversial pivot.

  
  

In sum, entrenched leadership usually stems from a mix of psychological comfort, fear of the unknown, structural inertia, and sometimes, a plain lack of digital savvy. 

Why We Should Empathize with Entrenched Leaders

It’s easy to paint entrenched leaders as villains blocking progress. However, a more empathetic view reveals that their resistance often comes from very relatable concerns. Understanding their perspective is crucial if you’re a change-maker trying to bring them on board.

First, these leaders carry the weight of responsibility for large, complex businesses. A TV network executive isn’t just responsible for innovation; they’re accountable for hundreds or thousands of jobs and existing revenue streams. Their cautious approach often stems from genuine concern: “If we overhaul our model and it fails, what happens to the company (and everyone in it)?” In the media world, where margins can be thin and failure is public, this pressure is intense.

Also worth considering, entrenched leaders have personal identities tied to their legacy business. A studio head who spent 30 years mastering theatrical film releases might feel a personal loss in shifting focus to streaming. It can feel like abandoning one’s life’s work. There’s an emotional hurdle – grief for the decline of a beloved model – that underlies their resistance. Being empathetic means recognizing that this isn’t just business; it’s personal. The media business has always required great deal of dedication from those who are fortunate enough to succeed in it, and reluctance often comes from a place of pride in what they built and fear that change could erode that legacy.

Another reason to empathize: fear of the unknown. Digital transformation can be intimidating. Imagine being a veteran TV exec suddenly hearing about algorithms, data analytics, direct-to-consumer tech, AI-driven recommendations – it’s like entering a foreign land where your leadership instincts don’t automatically apply. Many entrenched leaders privately worry about looking incompetent or losing their authority in a domain they don’t understand. Rather than expose their discomfort, they may double down on familiar territory. If you’ve ever helped a parent or older relative with technology, you know the mix of fear and pride that can surface – a similar psychology plays out in boardrooms.

Entrenched leaders also face external pressures. They might have boards and investors who are also conservative and reward short-term stability over long-term bold moves. They might have customers in older demographics still demanding traditional services. Balancing these stakeholder expectations with calls for innovation is a tightrope walk. In some cases, leaders fear that aggressive transformation could alienate core audiences, employees, or partners (for example, film studios long depended on theater chains – going direct to streaming could damage those relationships). These are valid concerns to manage.

Finally, empathy is important because to drive change, you need the buy-in of these leaders. If you approach entrenched leadership with hostility or by dismissing them as dinosaurs, you’ll only trigger defensiveness. By contrast, approaching with understanding – acknowledging the challenges and fears they face – opens dialogue. You can then address those fears (with data, pilot programs, etc.) in a collaborative way. As change agents, we should view entrenched leaders not as obstacles to bulldoze, but as partners to educate, learn from, and support. Empathy helps build trust, which is the basis for influencing anyone.

In short, entrenched leaders are usually protective, not obstructionist for its own sake. They are protecting what they know, what has worked, and what feels safe for their people and themselves. By walking a mile in their shoes, we can better frame transformation in terms that resonate with their values (like preserving the company’s legacy by adapting it for the future, rather than destroying what came before). Empathy doesn’t mean excusing stagnation, but it means acknowledging the human side of change. This mindset will make any transformation journey less combative and more constructive.

Strategies for Phasing in Transformation (With Entrenched Leadership in Place)

How can organizations innovate when the top brass is slow to change? The key is a phased, collaborative approach that works with entrenched leadership rather than against them. Here are several strategies content strategy professionals have found effective:

1. Build a Clear Vision and Communicate Early: One reason entrenched leaders balk is uncertainty about where the change leads. Painting a clear vision of the transformed business can alleviate that. Lay out a compelling narrative of why digital transformation is necessary (e.g., changing audience behaviors, new revenue opportunities) and what the end state could look like. Importantly, tie it to the organization’s core mission and OKRs. For instance, frame streaming not as “a tech overhaul” but as “bringing our beloved content to new generations on their terms, with a potential revenue increase of 15%.” A crystal-clear, data-based vision, repeatedly communicated, can start to align even skeptical leaders. If you show hesitation or lack clarity, you’ll “lose the organization,” as former Disney CEO Bob Iger observed of leading major change. So, over-communicate the why and how, until the top brass internalizes the plan.

2. Start Small with Pilot Projects and Quick Wins: Rather than pushing a giant all-or-nothing transformation (which can spook leadership and everyone else), start with incremental changes that demonstrate value. Identify a low-risk project where digital can make an impact – for example, a niche streaming app for a subset of content, or a trial of releasing one film online alongside theaters. By running a pilot, you contain the risk and cost. If it fails, it’s not catastrophic; if it succeeds, you now have a concrete proof of concept. Quick wins build credibility and earn trust. They give entrenched leaders real-world data to get behind. Many companies find that a phased rollout – testing new ideas in a controlled way – converts skeptics into supporters over time. Essentially, you’re de-risking the transformation by breaking it into digestible steps. Bonus points if you're able to solve a problems entrenched leaders face while you're at it.

3. Leverage Internal Champions and Cross-Generational Teams: Within any large media company, there are usually pockets of forward-thinkers – younger managers or digitally savvy staff who are eager to put their stamp on the company. Empower these people to lead from within, but pair them with experienced veterans in cross-functional teams. This blends fresh ideas with institutional knowledge. When an entrenched leader sees their own trusted lieutenants driving a project (instead of outside consultants or the IT department), it feels less like an alien invasion. Encourage mentorship swaps: tech teams educate senior leaders on new tools, while senior folks impart business context. This inclusive approach can soften a leader’s resistance because they see familiar faces involved and shared ownership of the change.

4. Align Transformation with Existing Goals: Find ways that digital initiatives support the company’s current objectives rather than seeming like a detour. For example, if a broadcaster’s goal is increasing audience engagement, show how a new streaming platform can boost total viewership minutes (perhaps combining linear and digital metrics). If revenue growth is a goal, present the business case for how an automated FAST service can open international markets or new ad streams. By linking the transformation to metrics the leadership already cares about, you make it a means to their ends rather than a conflicting agenda. This reduces pushback since you’re not asking them to abandon their focus – you’re enhancing it. Frame digital projects as solving problems the company already prioritizes. That way, leaders feel you are helping them achieve their goals, not imposing yours.

5. Education and External Perspectives: Sometimes leaders resist simply because they don’t know what they don’t know. Gentle education can go a long way. Arrange private demos of new technology or processes for the C-suite. Share case studies of competitors or industry peers who successfully transformed – seeing rivals do it can be motivating (nobody wants to be left behind). Even bringing in an outside advisor or industry veteran who successfully led a transformation elsewhere can influence entrenched leaders. Hearing it from a fellow executive who speaks their language resonates. The idea is not to confront, but to expose them to new information in a respectful way. Over time, this can shift mindsets. Many enlightened media CEOs have had their aha moments after visiting Silicon Valley companies or hearing a compelling outsider talk about the future of media.

6. Maintain Core Business Stability During Transition: One legitimate worry of entrenched leaders is that in chasing the new, you might drop the ball on the core business that pays the bills today. A strategy to address this is the two-speed (or dual) transformation model: continue to execute and even reinforce the core operations while parallelly developing the new. You might even set up a separate “digital unit” or taskforce that is somewhat insulated from the main business, so it can innovate quickly, while the main business unit remains focused on current operations. Assure leadership that the legacy business will not be discarded or disrupted overnight. In fact, provide data on how it will be augmented or at least maintained during the transition (for example, “We’ll keep running the cable channel as-is for now, but we’ll gradually build the streaming library on the side”). Showing a roadmap of gradual transition – with key decision gates to assess progress – can comfort leaders that you’re not betting the farm in one go. It’s a bit like remodeling a plane while flying: you ensure the plane keeps flying, changing one piece at a time.

Throughout all these strategies, patience and consistent engagement are vital. You’re effectively turning an aircraft carrier, not a speedboat. It requires persistent effort, reassurance, and adaptation based on feedback. By phasing in changes thoughtfully, you give entrenched leaders the time to adjust their thinking and see evidence of success. Many will eventually become champions of the transformation once they feel confident it’s working. And if they don’t, then the next section comes into play.

When Is It Time to Change the Leadership?

Sometimes, despite best efforts, the existing leadership just cannot or will not pivot. It’s a difficult scenario, but one that companies must face honestly and with courage. When is it time to replace the leader for the good of the organization’s future? 

Here are some signs and considerations:

• Chronic Pattern of Missed Opportunities: If your company has a history of missing the boat on new trends because leadership said “no” or delayed action, it’s a red flag. One missed opportunity can be a lesson learned; a consistent pattern suggests the leader is unable to evolve. For instance, if a TV network passed on launching a streaming app year after year and lost audience to Netflix/Amazon, that indicates entrenched leadership at the top. When you can directly tie lost market share or competitive disadvantage to leadership inaction, it’s a strong case that change is needed at the helm.

• Active Sabotage or Stonewalling: In some cases, leaders not only passively resist but actively block transformation. If a CEO or division head continually vetoes digital initiatives even after evidence of their potential success, they may be too entrenched to move forward with. This might manifest as budget refusals for tech upgrades, killing innovative projects, or sidelining progressive talent. If you’ve observed promising internal innovators leaving the company out of frustration, that’s a sign the leadership is stifling progress. At a certain point, working around a roadblock is impossible if the roadblock is the chief decision-maker.

• External Industry Shifts Reaching a Tipping Point: Sometimes the world forces the issue. If the market environment has changed so dramatically that sticking to the old ways is almost certainly going to lead to failure, and the current leadership still resists necessary moves, a change becomes urgent. A classic example: when streaming subscriptions surpassed cable subscriptions globally, any network CEO still solely focused on cable was arguably risking irrelevance. Boards will look at these macro trends and decide if the current leader is the right person for the next era. When the writing is on the wall for the industry and the leader remains in denial, it’s time to consider new leadership that can adapt to the new world.

• New Vision Needed (Restarting the Clock): Digital transformation often requires a multi-year vision and commitment. If an entrenched leader has lost credibility with the troops or stakeholders on this front, a new leader can re-energize the organization with a fresh vision. Sometimes a leadership change is symbolic as much as practical. It signals to employees, investors, and partners that the company is truly turning a page. For example, tech companies have famously brought in new CEOs when they needed to reinvent (think of Microsoft bringing in Satya Nadella to drive a cloud-first strategy after a period of stagnation). In media, we saw AT&T install a new CEO at WarnerMedia (Jason Kilar, formerly of Hulu) specifically to push streaming, indicating the old guard wasn’t moving fast enough. A new leader can break from the legacy mindset and champion the transformation without the baggage of “the way it's always been done.”

• The Cost of Doing Nothing Exceeds the Cost of Change (Listen Up, Hollywood): Ultimately, boards and owners have to weigh the pain of changing leadership against the pain of staying the course. If keeping an entrenched leader is clearly more dangerous (declining revenues, talent exodus, shrinking audience, innovation deadlock) than the disruption of a leadership shake-up, that’s the tipping point. It’s often said that companies change when the cost of not changing becomes intolerable. If all the data screams that a pivot is needed and the current leadership can’t execute it, the organization must find leaders who can. This might mean recruiting an outsider with digital expertise or elevating an internal change agent to the top role.

Changing leadership is never a decision to take lightly. Leaders embody a lot of tacit knowledge and relationships that are valuable. It can also jolt an organization culturally. Therefore, it should be the last resort when other methods have failed to produce movement. But in a fast-evolving digital and AI landscape, clinging to an entrenched leader out of loyalty or inertia will sink the ship. A new leader with the right mindset can be the catalyst that unlocks a stalled transformation.

It’s worth noting that changing leadership doesn’t always mean firing anyone outright. It could be restructuring leadership teams – adding a Chief Digital Officer or empowering a new generation of leaders in key roles. In some cases it means the existing leader recognizes their own limitations and brings in deputies who complement their gaps (that’s a best-case scenario). However, if the top leader fundamentally cannot embrace the new direction, a clean break is sometimes needed. The media industry’s history is full of examples where a change at the top preceded a successful pivot – and sadly, examples where a refusal to change leadership led to decline.

Next, let’s look at two concrete case studies in the media/entertainment world: one illustrating a failure to transform due to entrenched leadership, and one showing a successful transformation that overcame legacy resistance.

Case Study: Blockbuster – How Entrenched Leadership Doomed a Giant

Blockbuster’s story is a cautionary tale of an industry giant that fell victim to entrenched leadership in the face of digital disruption. In the late 1990s, Blockbuster Video was the titan of movie rentals, with thousands of stores across the U.S. and beyond. Its CEO and executive team were extremely successful executing the retail store model – so successful that they failed to see the world changing around them.

The first alarm came in the form of a little startup called Netflix. In 2000, Netflix’s founders approached Blockbuster’s leadership with an offer to sell Netflix for $50 million, just enough to get them out of debt at the time. Famously, Blockbuster’s CEO, John Antioco, laughed off the proposal. He regarded Netflix as a niche DVD-by-mail service, one that catered to a small segment of movie buffs and early tech adopters. In his view, it posed no real threat to Blockbuster’s brick-and-mortar empire. This wasn’t just a one-time lapse in judgment – it reflected a deeper mindset. The leadership was entrenched in the belief that physical stores and late fees (which were a huge part of Blockbuster’s revenue) would continue to dominate. They were blinded by their past success and underestimated how quickly digital streaming would alter customer habits.

As the 2000s progressed, signs of change grew. Netflix moved from mailing DVDs to streaming online video, capitalizing on faster internet speeds. Customers were flocking to the convenience of movies delivered to their mailbox or streamed on their laptop, rather than schlepping to a store and worrying about return deadlines. Blockbuster’s entrenched leadership responded slowly and half-heartedly. They did launch an online DVD rental service in 2004, but years too late – Netflix had already seized the market. When Blockbuster finally removed the hated late fees (after realizing how much goodwill they were losing), it backfired by creating a massive revenue shortfall with nothing to fill the gap.

Internal culture at Blockbuster mirrored its leadership’s stance – there was cultural inertia against change. Many employees and middle managers were also invested in the store-centric mindset. After all, the entire company’s processes, metrics, and incentives were built around retail locations. Shifting to digital meant not only new technology but a wholesale change in how success was measured (store revenue vs. subscriptions) and what skills were needed. Blockbuster’s top team simply didn’t push hard or fast enough to retrain and refocus the organization.

A dramatic twist in Blockbuster’s saga was the influence of activist investor Carl Icahn in the mid-2000s. Icahn pressured Blockbuster to cut costs and he ousted Antioco in 2007, installing new executives who also unfortunately lacked digital vision. The leadership shuffle, rather than empowering a digital pivot, resulted in even less experienced strategists at the helm regarding online transformation. It was a case of the wrong leadership change at the wrong time – new leaders, but still entrenched in old thinking (focused on immediate profitability vs. long-term tech investment).

Ultimately, the entrenched leadership’s refusal to truly embrace the streaming future led to Blockbuster’s downfall. By the time they recognized the magnitude of the shift, it was far too late. Netflix had locked in millions of subscribers and become synonymous with convenient home entertainment. Blockbuster’s late attempts – a partnership with Enron for on-demand video that fizzled, and a last-ditch plan to leverage kiosks – couldn’t move the needle. The company that once dominated Friday night movie rentals filed for bankruptcy in 2010, essentially undone by the very innovation it had scoffed at a decade earlier.

The tale of Blockbuster illustrates how entrenched leadership’s short-sightedness and resistance to change can sink even a market leader. Key lessons from this failure include: Never underestimate new technology or changing consumer preferences, don’t let lucrative legacy revenue streams cloud your strategic vision, and ensure that if you do change leadership, you replace it with forward-looking talent. Blockbuster’s leaders clung to their business model until it collapsed – a sobering reminder that in the digital age, yesterday’s success can quickly become tomorrow’s albatross.

As media technology continues to increase its speed of evolution, there will be so many more stories like this coming soon.

Case Study: Disney Transformed a Legacy Media Empire (Despite Resistance)

Disney’s evolution into a streaming powerhouse shows how a legacy media giant can successfully transform by combining bold leadership vision with respect for its heritage. The Walt Disney Company is nearly a century old, with a storied history in film and television. As of a decade ago, Disney was the epitome of a traditional media powerhouse – blockbuster movies in theaters, channels on cable TV (Disney Channel, ESPN, ABC), and a goldmine of DVD sales and licensing deals. Entrenched thinking could have been a huge obstacle here – after all, why upend a model that had worked brilliantly for decades? Yet, Disney managed to execute one of the most impressive digital pivots in the industry, launching Disney+ and reorienting for the streaming era. How did this happen?

In the mid-2010s, Disney’s leadership under then-CEO Bob Iger began to confront the writing on the wall: streaming was the future of content distribution. Internally, there were surely hesitations. Disney had extremely lucrative arrangements in the existing system – for instance, Netflix was paying hundreds of millions to license Disney films to stream on Netflix (easy money for Disney), and the company had an entire ecosystem built around theatrical releases and cable broadcasters. Early on, some Disney insiders were concerned: Would a Disney streaming service cannibalize box office revenue or upset cable partners? These were the kinds of legacy resistance questions that come naturally from an entrenched mindset.

Bob Iger addressed these concerns by making a compelling case that the risk of not transforming was greater. He often stated that reinvention was not optional: “the world is not staying the same,” and Disney needed to “consider what tomorrow will bring and perform well tomorrow”. One pivotal moment came in 2017, when Disney announced it would end its licensing deal with Netflix and pull its movies to prepare for its own streaming service. This was a bold and somewhat controversial move – it meant sacrificing short-term revenue and stepping on the toes of what was then the king of streaming. Iger’s decision exemplified overcoming the fear of cannibalization: he was willing to cannibalize Disney’s traditional revenue streams in order to build a direct relationship with consumers. It took foresight and nerve to convince Disney’s board and stakeholders that this was the right path.

Disney didn’t dive into streaming blindly. They methodically acquired technology and content to bolster their transformation. In 2017, Disney bought a majority stake in BAMTech, a streaming tech platform, to serve as the backbone of Disney+. They also continued investing in must-have content - acquiring key franchises (Marvel, Star Wars via Lucasfilm, etc.) in the years prior, ensuring that when Disney+ launched, it would have an unrivaled library. This dual approach of tech + content was crucial. It showed even skeptics within Disney that the company was going all-in to make sure the new venture succeeded.

Of course, not everyone inside Disney was immediately on board. There were reports of internal debates: How much resource to allocate to Disney+ versus traditional businesses? How to price it without undermining other channels? To ease the transition, Disney structured itself to allow both old and new models to coexist for a while. They continued theatrical releases and linear TV content, but also gave Disney+ top priority in long-term planning. Crucially, Iger and his team communicated a clear vision: Disney+ was to be the future streaming hub of Disney content globally, an ecosystem binding together Disney, Pixar, Marvel, Star Wars, and more. He was, by all accounts, extremely clear with his organization about why this mattered. He noted that in big change, “there’s built-in resistance in any organization…

You need to be incredibly clear about what you want to accomplish and why it is important… If you show any hesitation…you lose the organization.” This top-down clarity helped align Disney’s many divisions.

The result? Disney+ launched in November 2019 to great fanfare, and within about 16 months it amassed over 100 million subscribers globally, a feat that took Netflix a decade to achieve. By 2023, Disney’s combined direct-to-consumer platforms (Disney+, Hulu, and ESPN+) topped 200 million subscriptions, putting the company neck-and-neck with Netflix in the streaming wars. This rapid success validated the transformation. Any remaining internal resistance largely melted away as Disney+ proved its worth, not only as a new revenue stream but as a strategic platform for the entire company.

It’s worth noting that Disney’s transformation wasn’t without hiccups. After Bob Iger stepped down in 2020 (only to return in 2022), there were tensions under his successor around balancing streaming growth with profitability – a common challenge as legacy media tries to replace old revenue with new. However, by having made the big leap, Disney can now adjust and refine its strategy from a position of participation, rather than sitting on the sidelines. The company’s willingness to disrupt itself has generally earned praise. One media analyst observed that Disney’s shift was so significant because it allowed Disney to transform from a company about products and characters to one that sells entertainment ecosystems.

Disney’s successful pivot underscores a few important points about overcoming entrenched leadership:

• It often takes strong, visionary leadership to drive the change – Iger himself was not entrenched in the old ways; he was forward-looking and able to rally others. In a sense, Disney was fortunate to have a leader who championed the new direction from the top. This highlights how bringing in or empowering a transformation-minded leader can make all the difference.

• The company didn’t discard its legacy strengths, it brought them along into the new format. Disney’s rich content library and brand were legacies, but instead of those being a ball and chain, they became the crown jewels of the streaming service. For European context, we see a similar pattern with the BBC: a very legacy institution that succeeded in digital by leveraging its strengths (the BBC iPlayer in the UK, launched way back in 2007, was one of the first broadcaster VOD services and is now core to BBC’s reach, delivering billions of streams per year). In both cases, the legacy content/quality was married to new distribution.

• Disney managed internal resistance by phasing the transformation. They didn’t shut down TV channels on day one or stop all DVDs immediately; instead, they gradually reallocated focus. This gave traditional parts of the business time to adapt. Empathy was evident in how Iger handled the team – he often spoke about maintaining Disney’s storytelling values (something the old guard cared deeply about) while updating the delivery mechanism.

The Disney case shows that entrenched legacy need not be an anchor if the leadership can articulate a new vision and be willing to take calculated risks. It stands in contrast to Blockbuster - where Blockbuster laughed and ignored the future, Disney embraced disruption, even at short-term cost. Not every media company has Disney’s resources, of course, but the principles hold: Bold leadership, clarity of purpose, leveraging legacy assets in new ways, and executing methodically can overcome even deeply rooted internal resistance.

Conclusion

Digital transformation in the streaming/TV/film sector is as much a human journey as a technological one. The clash between entrenched leadership and disruptive innovation is a recurring theme in both U.S. and European media industries. We’ve seen how sticking too long to old habits (the “we’ve always done it this way” mindset) can sabotage a company’s future, and how, conversely, respecting the past while boldly innovating can lead to new heights.

For content strategy professionals and change leaders, the takeaways are clear: Understand the roots of resistance, be it fear, pride, or simple lack of knowledge, and address them with empathy and data. Work with your legacy leaders through clear communication and phased strategies, but also know when to press for new leadership if the old guard simply can’t steer the ship into new waters. In practical terms, success requires blending old and new: New tech and platforms combined with the valuable content, experience, and brand equity built under the legacy regime.

Entrenched leadership doesn’t automatically spell doom. Some leaders can transform themselves, shedding old paradigms and championing change – those who do often turn into the strongest allies for transformation. Others may need a push, or ultimately, a replacement. The story is different for every organization, but the need to stay agile and responsive to audience behavior is universal.

In an era when a streaming service launched from a garage can challenge century-old studios, no media company can afford complacency at the top. Whether you’re advising a traditional broadcaster in Europe or a Hollywood studio in the U.S., remember that behind every strategic pivot are people who must buy into it. As you craft strategies, factor in the psychology of leadership, not just the market analysis. Bridging the gap between legacy and innovation is the real art of digital transformation. With patience, respect, and resolve, it’s possible to turn even the most entrenched leadership into champions of change; or at least guide the transition to leaders who will. The future belongs to those willing to reimagine themselves, no matter how deep their roots run in the old soil.