The Innovator’s Dilemma in Established Enterprises: Why Success Can Be Your Biggest Threat

Clayton Christensen’s The Innovator’s Dilemma remains one of the most important pieces of thinking in modern business strategy—and yet, nearly three decades on, its warnings are still ignored by many large enterprises. The dilemma is simple: the very things that make your organisation successful today—processes, customer focus, and risk-averse culture—can actively prevent you from surviving tomorrow.

Success is Built on Optimization, Not Disruption

Established companies excel at refining existing products, improving operations, and keeping their best customers happy. Their incentives are aligned with performance, not experimentation. New technologies that appear underpowered or too niche are often dismissed, especially if they cannibalise core revenue streams.

But that’s precisely the trap.

While you’re improving a product line by 10%, a startup is quietly rethinking the entire category. By the time their “inferior” product matures, they’ve taken the market you thought was unshakable.

Case in Point: Barnes & Noble and the eBook Revolution

Barnes & Noble was once the undisputed king of brick-and-mortar bookselling in the US. When Amazon launched the Kindle in 2007, eBooks were a curiosity—low in quality and reach. Two years later, Barnes & Noble responded with the Nook, but rather than giving it the freedom to disrupt, they forced it to play by the rules of their existing retail empire.

The Nook team had to align with priorities like printed book sales, publisher relationships, and store traffic. Instead of betting on digital with conviction, they treated the Nook as a side project. Amazon, meanwhile, doubled down on Kindle as the future of reading.

Barnes & Noble had the right idea—but they weren’t willing to let a new idea threaten their old one. And that’s the dilemma in a nutshell.

Why Enterprises Struggle With Disruption

  1. Metrics are backward-looking – ROI, efficiency, and market share are poor indicators of future risk.
  2. Customer voice is over-weighted – Your biggest clients often ask for better versions of what exists, not what’s next.
  3. Success creates bureaucracy – Layers of approval and aversion to failure choke experimentation.
  4. Innovation doesn’t scale linearly – A $1 million idea won’t excite a company chasing $1 billion targets.

What You Can Do About It

As a technology leader, you’re in a unique position to challenge this inertia. Here’s how:

  • Create a protected innovation space – Whether it’s a lab, a spin-off, or a skunkworks team, innovation needs room to breathe outside core processes.
  • Fund small bets consistently – Don’t wait for a “moonshot.” Encourage many small, fast, and cheap experiments.
  • Measure different things – Instead of traditional KPIs, track learning velocity, customer insights, and time-to-prototype.
  • Build a culture that rewards curiosity – Make it safe to ask “what if,” and honour lessons from failed attempts.

Final Thought: Disrupt Yourself Before Someone Else Does

The innovator’s dilemma isn’t about startups vs. giants—it’s about mindset. In a world of accelerating change, the companies that survive will be those that can simultaneously execute on today’s business and experiment with tomorrow’s.

If you don’t build the thing that makes your current product obsolete, someone else will. Probably sooner than you think.