How to Avoid Making the Same Fatal Mistake That Led to the Demise of Sears
•February 13, 2026
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Companies Mentioned
Why It Matters
The lesson highlights a universal risk for companies confronting digital disruption, showing that improper integration can accelerate decline and erode shareholder value.
Key Takeaways
- •Sears integrated innovation within legacy, stifling growth.
- •New initiatives clash with old processes, causing inefficiency.
- •Leaders must separate legacy systems from disruptive ventures.
- •Successful transformation requires autonomous units for emerging technologies.
- •Ignoring this principle risks revenue loss and brand collapse.
Pulse Analysis
Sears’ story reads like a cautionary case study for today’s digital transformation leaders. In the late 1980s the retailer operated a portfolio that resembled modern tech conglomerates—financial services, real estate, and early online platforms. Yet instead of allowing these units to evolve independently, Sears attempted to graft them onto its traditional retail framework. The resulting friction slowed decision‑making, diluted focus, and ultimately prevented the company from capitalizing on its own innovations, leading to a steady erosion of market relevance.
The core principle DeGraff promotes—"never put the new into the old"—addresses a deeper organizational inertia. Legacy systems are built to preserve existing processes, while disruptive technologies demand flexibility and rapid iteration. When a company forces a startup‑like venture into a bureaucratic structure, cultural misalignment and resource constraints often choke growth. Companies such as Amazon and Alphabet illustrate the opposite approach: they spin off experimental divisions, grant them operational autonomy, and only integrate successful models after they have proven scalability.
For contemporary executives, the actionable path is clear. Establish separate innovation labs or venture arms with distinct governance, budget, and performance metrics. Encourage cross‑functional talent exchange to seed fresh perspectives without diluting core business efficiency. Regularly assess the health of legacy units and be willing to sunset underperforming lines. By preserving a clear boundary between established operations and emerging opportunities, firms can maintain agility, protect revenue streams, and position themselves to thrive amid continuous market disruption.
How to Avoid Making the Same Fatal Mistake That Led to the Demise of Sears
When faced with disruption, Sears made a common but fatal error. Many leaders today are repeating the past.
*EXPERT OPINION BY Jeff DeGraff, author, The Art of Change: Transforming Paradoxes into Breakthroughs
Feb 13, 2026
Photo: Getty Images
Every leader facing disruption feels the same pull:
“Let’s integrate the new into what we already do.”
It sounds responsible, mature, and safe. It reassures boards, calms investors, and signals control. It has also quietly cost companies billions—and ended more leadership careers than any competitor ever has.
That instinct—more than technology shifts, market shocks, or outside threats—is what kills organizations.
I teach a simple first principle to leaders navigating change: Never put the new into the old. Not because it is inefficient, but because it is lethal. The old is built to preserve itself. The new is built to break patterns. When you force one into the other, the result is not balance but suffocation.
To understand why, you have to understand Sears.
In the late 1980s, Sears was not a fading retailer waiting to be disrupted. It was a proto‑digital empire hiding in plain sight. Inside the company lived financial services (Allstate and Discover), real estate (Coldwell Banker), early online platforms (Prodigy), and diversified retail experiments. Strip away the brand names, and it looks uncannily like Amazon or Alphabet decades before their time.
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