Building digital dexterity: the new leadership imperative for successful transformation

Harvard Business School research highlights that organisations succeeding with digital change focus on reshaping how people work, think and collaborate, emphasising long-term cultural and behavioural shifts over technology rollouts alone.

Leaders who are succeeding with digital change are focused less on technology rollouts and more on reshaping how people work, think and collaborate. Research from Harvard Business School’s Leadership Initiative, led by Linda A. Hill,...

finds that organisations making the most headway aim to build a “digitally dexterous” workforce , employees who both want and know how to apply new technologies, including generative AI, to create value and spot future opportunities.

The HBS team, drawing on longitudinal case studies, roundtable discussions with more than 240 leaders and digital natives, and cross‑sectional surveys of over 8,300 leaders across 109 countries and 11 industry sectors, identifies four repeatable practices behind progress. The first is reframing the task: instead of treating transformation as a sequence of tool purchases or training programmes, leaders reposition it as a change in work itself, redesigning processes so technology becomes an integral enabler of everyday decisions and delivery. The second is visible, sustained involvement from senior leaders: executives must signal priorities, model new behaviours and remove structural obstacles. The third practice bridges diverse people and perspectives , connecting digital natives, domain experts and frontline staff so technical possibilities meet operational realities. Finally, successful efforts are long‑term commitments, not time‑boxed projects; leaders persist in coaching, experimentation and iterative change until new habits stick.

Those findings align with vendor and analyst research that underscores the scale of the challenge. According to Gartner, only about 9% of employees demonstrate high levels of digital dexterity, making it a scarce capability, and 83% of leaders report difficulty making meaningful progress on digital transformation. Gartner also reports organisations with strong digital dexterity are roughly 3.3 times more likely to succeed in their transformation efforts, a gap that highlights the commercial payoff of behavioural as well as technical change.

Practical measures for closing that gap stress culture and capability in tandem. Atlassian advises building a culture of continuous learning and safe experimentation, supplying accessible tools, fostering cross‑functional collaboration and measuring outcomes so initiatives can be refined. Industry guidance from TriNetix and others frames digital dexterity as a mix of technical fluency and behavioural qualities , adaptability, resilience, empathy, proactivity and collaborative skill , rather than a narrow IT competency.

The implication for leaders is clear: training alone rarely produces the desired shift. The Harvard researchers repeatedly heard executives say their organisations had invested heavily in tools and data only to find people unwilling or unable to use them. To overcome that, leaders must redesign work and create the conditions for learning on the job. Psychological safety, iterative feedback and opportunities to apply new skills to real problems emerge as essential ingredients. As Harvard’s work cites earlier research on teams, learning flourishes where people feel able to experiment and speak up without fear of censure.

Organisational design choices matter. Leaders who accelerate dexterity flatten barriers between functions, create rotating roles or embedded partnerships between technologists and business teams, and build metrics that reward adoption and value creation rather than solely tracking project completion. Chief Information Officers can play a central role by translating technical possibilities into clear business use cases and by equipping managers with the language and tools to coach their teams through adoption, according to Gartner guidance for CIOs.

There are difficult trade‑offs. Reallocating people to cross‑functional work, sustaining long‑term investment in coaching, and tolerating early setbacks during experimentation all require patience from boards and investors accustomed to discrete deliverables. For companies that persist, however, the returns include faster innovation cycles, higher-quality decisions informed by data and, critically, a workforce capable of applying new technology as it emerges.

Building digital dexterity is therefore less a one‑off programme and more an ongoing managerial capability: reframing the challenge, committing from the top, connecting people across boundaries and treating transformation as a long haul. Industry data and practitioner guidance converge on the same message , the analogue work of shaping minds, incentives and interactions is the key to realising the promise of digital tools.

Source: Noah Wire Services