Project Management

The Effects of Poor Leadership on Digital Transformation Initiatives

Grace Willis, MBA, SPC6, PMP, CSM, CSSGB

Grace Willis is an agile transformation practitioner.

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“Digital transformation” has become a diluted, overused buzz phrase among corporate giants. Many market leaders claim to be on their digital transformation “journey”—yet things are not working out very well.

The problem with many digital transformations is simple: lackluster leadership. There are many manifestations of the problem, including a lack of…

  • Vision
  • Objectives and key results
  • Customer-centricity
  • Value stream analysis
  • Process improvement activities
  • Change management integration

There is also an overabundance of wasteful meetings and workshops with unclear outcomes. The backdrop of this is corporate bodies jostling for power and recognition as they contribute to poor transformation initiative outcomes.

I had my own tour of duty as a Digital Transformation Lead” within a Fortune 100 company (2022 ranking). I can wholeheartedly attest to my personal experience with digital transformation failure, which aligns with the findings of a 2020 Boston Consulting Group study concluding that 70% of digital transformations fall short of their objectives.

My “research” is primarily on-the-job experience—not of the ilk of venerated PhDs and top-tier management consulting firms, but simply that of observations from stakeholders in this game that everyone is jumping into like a Double …


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"Wise men talk because they have something to say; fools, because they have to say something."

- Plato

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