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3 Uncomfortable Questions For Target’s New CEO

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Longtime insider needs candor, clarity and courage to revitalize retailer
The impulsive reaction to Target’s long-overdue CEO change is — what took so long?
The bull’s-eye retailer’s well-publicized include plateaued sales since 2022 and shares down 60% from their 2021 peak. During outgoing CEO Brian Cornell’s eleven-year tenure, Target stock grew a pedestrian, cumulative 76%. That’s roughly 5% per year, just slightly over compounded inflation and risk-free rates. Conversely, rival Walmart and the S&P 500 delivered 313% and 231% returns, respectively, over that stretch.
Those dismal marks signal far scarier AI-era problems newly-appointed CEO, company lifer Michael Fiddelke must fix. Ultimately, his prospects hinge on a singular question —who (name names!) can and will you trust, welcome and encourage to ask the candid, uncomfortable and unvarnished questions every effective executive needs?
Here are three specific examples for Fiddelke:
1. Will you settle for the entrenched governance structure?
Courageous CEOs demand exceptional boards. Target’s 2025 proxy statement reveals many glaring digital era stewardship gaps.
The board lacks a technology committee and the proxy mentions “cybersecurity” just nine times. “Artificial intelligence” astonishingly appears just once. On second glance, perhaps that’s not surprising. Only two independent directors, healthcare CEO Gail K. Boudreaux and former media and charitable foundation executive Monica Lozano, are tagged with “digital tools/data analytics” qualifications.
Yet, all eleven independent directors are designated “expert” in senior leadership, risk management and financial management. The adrift past decade suggests otherwise and the current mix likely can’t offer “elite sparring partner” oversight to sharpen Fiddelke’s COO and CFO background.
No new director has joined the board since 2022. Excluding Cornell, who held the often-problematic dual title of Board Chair and CEO, the average age exceeds 66 years.

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