The biggest part of our digital transformation is changing the way we think. — Simeon Preston
—What lingers after this line?
Beyond Technology Alone
At first glance, Simeon Preston’s remark seems to address software, systems, or automation, yet its real emphasis falls elsewhere. He argues that the most significant element of digital transformation is not the machinery itself but the mental shift required to use it well. New tools can be purchased quickly; changing habits, assumptions, and decision-making patterns is far slower and far more consequential. In this sense, the quote corrects a common misunderstanding. Organizations often treat transformation as an IT project, but Preston suggests it is fundamentally a human one. The deeper challenge lies in teaching people to think experimentally, act with agility, and question long-standing routines that once felt untouchable.
Why Mindset Becomes the Real Battleground
From there, the quote points to the true source of resistance in many institutions: not a lack of hardware, but a loyalty to familiar ways of working. Even when companies invest heavily in digital platforms, progress stalls if leaders and teams continue to think in rigid hierarchies, slow approval chains, or fixed annual plans. The technology may be modern, while the culture remains old. This is why change experts so often focus on mindset before process. John Kotter’s Leading Change (1996) argues that transformation succeeds when people feel urgency and embrace new behaviors, not merely when structures are redesigned. Preston’s insight fits that tradition, highlighting that digital progress depends on internal adaptation as much as external innovation.
Learning to Value Experimentation
Once mindset becomes central, experimentation naturally follows. A digitally mature organization tends to reward testing, iteration, and learning from small failures rather than punishing every misstep. That is a profound psychological shift, especially in workplaces shaped by caution and predictability. Thinking differently means accepting that not every initiative will work perfectly the first time. For example, Amazon’s shareholder letters, especially those by Jeff Bezos, repeatedly frame experimentation as inseparable from invention: if you know in advance it will work, it is not really an experiment. Preston’s quote echoes this logic. Digital transformation asks people to replace certainty with curiosity, and that can be more disruptive than installing any new platform.
Leadership as a Model for Change
Consequently, the burden falls heavily on leadership. If executives speak about innovation while rewarding only caution, employees quickly learn that transformation is rhetorical rather than real. By contrast, when leaders model openness, data-driven thinking, and willingness to revise assumptions, they make cultural change visible. The organization then sees that new thinking is not a slogan but an expectation. Satya Nadella’s renewal of Microsoft, described in Hit Refresh (2017), is often cited for this reason. He emphasized a shift from a ‘know-it-all’ culture to a ‘learn-it-all’ culture, and that change in attitude helped support broader technological renewal. Preston’s statement aligns neatly with such examples: transformation begins in the mind before it appears in the system.
From Individual Habit to Organizational Culture
Yet the quote also works at a more personal level. Every employee participating in digital transformation must reconsider daily habits: how to collaborate, how to interpret data, how to respond to customer feedback, and how to keep learning as tools evolve. In that way, changing the way we think is not an abstract corporate slogan but a practical discipline repeated in countless small decisions. As a result, the biggest part of transformation becomes cumulative cultural change. One person adopts a new workflow, one team shares knowledge more openly, one department trusts analytics over intuition alone, and gradually the institution behaves differently. Preston’s insight endures because it reminds us that digital transformation is ultimately not about becoming more digital, but about becoming more adaptable.
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