Target CEO Michael Fiddelke on preserving what works without blocking what needs to change. A practical framework for leaders facing the legacy-versus-reinvention challenge.
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Michael Fiddelke started at Target as an intern. Twenty years later, as he prepared to take the CEO role, he sat down with HBR Executive to talk about a problem every long-tenured leader faces: how to keep what works without blocking what needs to change.
The conversation, part of HBR's Executive Live series, circled around a tension that is easy to name and hard to manage. A company that has been successful for decades builds up institutional memory, processes, and cultural habits that got it where it is. Those same assets can become liabilities when the market shifts. Fiddelke's framing was direct: the goal is not to tear down the old but to figure out which parts of the legacy are still earning their keep.
He pointed to Target's physical stores as an example. The brick-and-mortar network, built over decades, looked like a disadvantage when e-commerce took off. Target turned it into a moat by using stores as fulfillment centers for online orders. Same infrastructure, different operating logic. The lesson, as Fiddelke described it, was that reinvention does not always mean starting from zero. Sometimes it means reusing the same assets in a new way.
The harder part, he said, is cultural. An organization that has won a certain way tends to keep playing that game even when the rules change. Fiddelke described the discipline of asking, at every level, whether a given practice still serves the customer and the strategy. That sounds simple. In practice, it means having uncomfortable conversations about sacred cows.
He also stressed the value of outside perspective. Leaders who have spent their whole careers inside one company risk blind spots. Fiddelke said he makes a point of studying how other retailers, and companies outside retail entirely, handle similar transitions. The goal is not to copy but to borrow the logic and adapt it.
The full conversation is available to HBR Executive subscribers. For anyone running a business with a long history, the core question Fiddelke posed is worth holding onto: what are you preserving because it still works, and what are you preserving just because it is familiar?
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