Davide Bonazzi
Leaders across the globe have told us that despite having made significant investments in digital tools and data, their people are unwilling or unable to use them.1 Repeatedly hearing this lament led us to ask a critical question: Why are some leaders making more progress than others with their digital transformations?
In 2020, when we first began researching what it takes to lead in the digital era, we defined digital transformation as the evolution of an organization’s processes, systems, and talent in order to take full advantage of the possibilities offered by digital technologies, including big data, analytics, and artificial intelligence. Five years later, we have found that leaders who are making more progress on digital transformation have gone well beyond our original definition. They have redefined the challenge: Their ambition is to build what we now refer to as a digitally dexterous workforce — a workforce that is both willing and able to take advantage of new technologies, such as generative AI, to deliver innovative solutions and prepare their organizations for future opportunities.
Our research team, comprising academic researchers, executives who have led cultural and digital transformations, and digital natives, set out to uncover what sets apart leaders who are reporting more progress building digital dexterity in their organizations. Since 2017, one of us (Linda) has been writing longitudinal case studies on diverse leaders and companies that have been grappling with digital transformation. Since 2022, we have supplemented this research with global roundtables of over 240 leaders and digital natives and data from cross-sectional surveys of over 8,300 leaders across 109 countries and the 11 sectors identified in the Global Industry Classification Standard framework.2 In our annual surveys, we asked respondents to rate their perception of their organization’s progress on a 1-to-6 scale (1 indicating no progress and 6 indicating a lot of progress). For our analysis, we considered those reporting a progress level of 5 or 6 (30% of respondents in the 2025 survey) as reporting more progress.
We’ve found that the leaders making the most progress understand that they face a workforce challenge, not a technology challenge (they reframe the problem), are closely involved in the effort (engage with employees and the process), work to understand employees’ concerns (bridge gaps between people and perspectives organizationwide), and have a long-term perspective toward transformation (sustain a long-term commitment to it). In this article, we’ll explore how leaders are deploying each of those four practices.
Reframe the Challenge
Leaders who are making more progress with their digital transformations are expanding their mindset about leading in the digital era. It is less about technology and more about people and how work gets done. This means that they are prioritizing cultural transformation and reframing the challenge to focus on helping employees adopt new ways of working. As a consequence, employees are more willing to collaborate, experiment, and learn how to use new digital tools and data to drive positive business outcomes.
Those new ways of working are centered on developing five critical organizational characteristics: data-informed decision-making, cross-functional collaboration, customer focus, continuous learning, and comfort with change. Each year since 2021, respondents have identified these same five organizational characteristics as being the most important in building a digitally agile organization. Data-informed decision-making requires that individuals have access to relevant data and are fluent enough with analytics to glean insights and develop their business judgment. Cross-functional collaboration demands that employees work across silos to solve problems and deliver a more seamless customer experience, and the shared focus on customers helps keep groups aligned as they figure out how to use digital tools to add value. A culture of learning and experimentation is foundational to innovative problem-solving and the agility required to adapt to evolving customer expectations. Developing each of those capabilities requires that leaders create an environment in which employees are willing to do the hard work of absorbing and responding to the increased pace of new digital technologies — which requires new mindsets, behaviors, and rethinking ways of working.
Those leaders who reported more progress on their digital transformation journeys were more likely to report that those capabilities described their organizations. One executive noted that their efforts had stalled because a technology-first perspective meant that they were simply “putting software on top of conventional organizational structures and processes.” Instead, as another leader noted, the key question to ask is “How does work need to get done today, how does [digital] fit in, and how do we fit people into the picture?”
In one health care system we studied, the senior leadership team recognized early on that integrating digital tools and data into the work of physicians and nurses would require cultural and operating model shifts. They made significant investments in digital technology and tools, guided by the belief that all technology should be user-friendly and empowering for those who use it. IT, business intelligence (BI), and the organizational effectiveness groups worked hand in glove to make sure their employees would be able to collaborate and experiment together by using technology to harness diversity of thought and deliver a patients-first experience.
These groups consulted with physicians and nurses about the design and implementation of new digital tools and, in doing so, introduced a self-service model to enable caregivers to access insightful information, not just raw data, on their own. The BI group educated physicians and nurses on basic data literacy, including interpreting graphs and basic statistics and learning how to better phrase questions to obtain meaningful insights. Before long, more nurses began to run A/B experiments as a part of their daily routines. Physicians and nurses began working with the IT and BI groups on patient wait-time dashboards to coordinate communication and care across the patient experience in real time. One executive leader remarked that staff members’ level of engagement was among the highest he had ever witnessed.
In another case, an automotive CEO we studied found himself tasked with turning around the core business while also building out a new business focused on electric and software-defined vehicles. He knew that this turnaround would require more than just a new technological infrastructure: It demanded a digitally dexterous workforce that could transform a traditional legacy organization into a tech and mobility services company. He realized that he could fulfill his mandate only if he addressed the five organizational capabilities identified above.
The CEO set up a cross-functional group of 30 high-potential leaders (reporting into the C-suite), whose mandate was to translate the corporate vision into an actionable strategy and execution plan. He provided them with the time, space, and freedom to collaborate and move the business into the future. The team set up a design-thinking studio on the first floor of the company’s headquarters, where everyone in the office could see the leaders hard at work and the CEO could visit them almost daily to hear about their progress. Turning these high-potential leaders into transformation champions shook up long-standing cultural and hierarchical norms at the company. The CEO was signaling a new way of working that induced some anxiety and resistance at first, especially when he challenged ideas generated during design-thinking sessions. But with the encouragement of the CEO and buy-in from their managers, the high-potential group continued to ideate, and their comfort with change grew. Even C-suite leaders who had initially felt sidelined became advocates for this new way of working. As one senior leader noted, “The people who were [in the group] were thrilled because it was a recognition for them … and while [they] were laying out the midterm actions, [the leadership team] took care of the fires and made sure that we were getting out of some deep holes.” By reframing the challenge ahead as not just a singular leadership task but an organizational alignment toward cross-functional and cross-generational teams, the company was able to stabilize its finances, modernize its product lineup, and reorganize into new divisions not just to adapt to emergent change but also to actively shape it.
We’ve found that leaders’ shift in perspective to focusing on culture and work-process change often comes with experience. Our survey data shows us that one of the differences between organizations reporting more progress in digital transformation and those reporting less is that organizations reporting greater progress are focusing more on two areas: employee experience and cultural transformation. A leader we spoke with at a company in the Asia-Pacific region said that he initially saw digital transformation as being all about IT and tools, but as he grappled with employee resistance to new digital tools and data, he began to understand the deep cultural shift required.
Engage From the Top
As leaders reframed the challenges ahead, they also came to understand just how much of an active role senior leadership needs to play in driving toward digital dexterity. Because digital transformation is a holistic change that requires changing attitudes and behaviors across the enterprise, the CEO or senior team must lead the change. The data from our 2025 survey indicated that organizations where the CEO or the C-suite led the digital transformation process (35% of the companies) reported more progress. Top leadership has to demonstrate their commitment by being actively engaged and by dedicating their time and attention to the change efforts. (See “How Attention to Culture Change Pays Off.”) The most successful leaders walk the talk; they don’t delegate responsibility. Rather, they act out of a sense of urgency and model the types of mindsets and behaviors they expect to see from their colleagues throughout the company.
In one global manufacturing company we studied, its CEO stayed close to the high-priority initiative of democratizing innovation for its 10,000-plus employees by working closely with his executive team and chief of staff (whose office was located in the top executive suite). The company launched a digital platform to collect innovative solutions generated by employees from across functions and geographies, many of which involved technology. Employees could use the platform not only to submit their own ideas but also to review others’. Senior leadership monitored which ideas gained traction and, based on reviews, chose a subset of ideas to fund and implement. Every quarter, nominated individuals and teams had the opportunity to present their ideas to senior management.
Despite his busy schedule, the CEO attended all of the quarterly meetings. He appreciated the opportunity to interact with the diverse population of employees who presented ideas, and, thanks to the transparency of the approach, he often learned of promising new initiatives to move the business forward. One proposal led him to ask the company’s CTO to assemble a team to explore and scale the idea, which ultimately led to the launch of a new market segment.
The CEO’s high level of engagement was not lost on his employees. Many described how his involvement encouraged them to develop and bring forth new ideas about how to improve their processes or grow the business.
Leaders must also demonstrate their willingness to engage with the technologies that they are asking their employees to embrace. In fact, nearly half of our 2025 survey respondents identified “data savviness” as the third most important leadership quality in leading transformation, after “adaptability” (75%) and “curiosity” (52%). Eighty percent of respondents who reported greater progress (as opposed to the 36% of respondents who reported less progress) in their digital transformation journeys described their C-suite as “very tech savvy” or “extremely tech savvy.”
Interestingly, in our early surveys, data savviness was not seen as a critical requirement for leaders. We believe that the advent of generative AI has led executives to understand that although they don’t need in-depth technical knowledge, they must “understand the digital context, language, trends, and opportunities,” as one executive in India put it. For senior leaders, this often means joining company hackathons, participating in hands-on experiments with AI use cases, or using data analytics to inform their decisions. That last one is critical: In our roundtable conversations, leaders consistently emphasized how difficult it was to get employees to draw on data when making decisions. “It is not a technical issue; it is a cultural issue,” one executive based in Africa told us.
This is where leaders’ rhetoric matters; employees are more likely to resist using data when the call is for data-driven decision-making as opposed to data-informed decision-making. For many, this implies that the data is a substitute for, rather than a complement to, their own expertise and experience. As one European executive noted, leaders must be the first ones to begin using data for decision-making — modeling the curiosity, a willingness to try new tools, and the ability to adapt that they want to see in their workforce.
One leader we studied was charged with building a culture of innovation to create an end-to-end physical and digital clinical supply chain that harnessed AI capabilities. He recognized that his senior team had to drive the change from the top. He enrolled in an executive education class to gain a better understanding of AI and what it would take to build the digital and cultural infrastructure required to transform AI results into actionable insights. He then designed training for his leadership team based on his class’s curriculum and made sure everyone attended. All of the leaders were required to work with their teams to generate AI use cases for their functions and the enterprise. The executives were surprised at just how many innovative ideas their teams came up with to improve their processes. They also learned the limits of and financial costs associated with using AI, as well as the enterprise risks and ethical dilemmas associated with these digital tools.
As the most senior person in the room, this leader’s time, attention, and role modeling sent a powerful message within his team and throughout the organization: Building and leading a digitally dexterous workforce was a priority. “If the most senior leader in the group wants to ask his team to do something, then they need to invest enough time to learn about the technology themselves,” he told us. “I had to demonstrate that this was worth learning about — that it was not a shiny object.” Now, the organization is realizing what may be possible to achieve by using different technologies, like generative AI, and building out governance models for deploying those technologies.
Bridge People and Perspectives
Leaders who make more progress than others in building a digitally dexterous workforce understand that attending to culture and employees’ anxieties about change is critical. This is where leaders’ curiosity and empathy come into play. They must take the time to engage in dialogue with people throughout their organizations and create more psychologically safe spaces where people can speak honestly about how they feel about the technology.3 Some will be worried about changes to their jobs, including job security, whereas others will be excited by the new opportunities digital tools can bring.
Successful leaders in this context must act as “bridgers.” The bridger’s role is to figure out how to build partnerships across organizational boundaries by translating across differences — differences in priorities, constraints, capabilities, and working styles. It isn’t easy to build a sense of partnership, but it is essential if people are going to be willing to take risks and work in different ways. Among other things, bridgers work to establish a common language and create opportunities for productive interactions to foster relationships based on mutual trust, commitment, and influence.4 Trust and how to build it were always major topics of conversation in our roundtables. Here, again, rhetoric matters: The leader who set up training for his leadership team called AI augmented, not artificial, intelligence; emphasized how technology could make team members more innovative, not just more productive; and spoke of the need to evolve rather than to change.
Leaders who bridge between different perspectives effectively don’t write anybody off; they try to bring everyone along. They listen to individuals and don’t make assumptions about attitudes based on demographic characteristics. For example, one executive in Latin America noted that sometimes the people most excited by technology were older employees. Such leaders recognize that the kind of innovative problem-solving they hope the technology and data will enable requires diversity of thought and experience.
Still, there are often differences between people who have been brought in from the outside to accelerate the digital process and those who are long-tenured and possess institutional knowledge, as well as between business and technology teams and different functions, regions, and even generations. “Some parts of the organization are more advanced than others,” one leader told us. Leaders need to show support to those who are lagging, discouraged, or worried.
For some of our roundtable participants, bridging in their organizations also involved aligning people around a common ambition that “made all feel engaged and valued,” as one executive from the Middle East and North Africa region put it. Many described sitting down informally with different groups within their organization in order to understand any trepidations employees might have about working with new technologies. They found out more about workers’ frustrations with the company not moving quickly enough to deploy the latest technology, or about working with colleagues whose attitudes toward technology or workplace roles and experiences differed from their own. In a Latin American company that focused on food technology, one leader created a system in which everyone hired to work in the corporate office spent a week in the company food kitchens as a part of their onboarding, to understand the opportunities and challenges of digitizing front-line processes. This created a more open and collaborative environment, where people in the organization felt more comfortable asking questions and learning across levels.
One leader at an airline company who was charged with launching digital solutions worked to connect every division of the company with external partners, such as research institutions, universities, startups, and venture capital firms. To do this, she hired a dedicated team of bridgers capable of engaging with diverse stakeholders. They introduced design-thinking workshops to people in the company to familiarize them with a new way of working that was multifunctional, experimental, and customer-focused. Their efforts included creating a biometric boarding pass, which required collaboration across IT, operations, and marketing, as well as partnerships with a biometric tech startup and government border and security agencies. By bringing diverse groups together, translating across perspectives, and integrating new technologies, this leader exemplified how embracing differences can result in a more digitally agile workforce — ensuring that employees can work in the new ways required to get value out of the latest technologies.
Sustain a Long-Term Commitment
Our research confirmed what we have always known: Culture change takes time. Those who reported making more progress on their digital transformation journeys had been at it for some time. However, time alone is not enough. Investments in digital tools and data will not pay off until people are able to develop the new mindsets and behaviors required to fully benefit from them. If digital dexterity is the ambition, leaders must be prepared to sustain a long-term commitment to the lengthy journey ahead and lead with tenacity and resilience.
One executive we studied initially thought that digital transformation would take him three years to execute. A few years in, he realized how wrong he was. His organization’s digital transformation took almost eight years. The company had many legacy systems, and it spent six years just building a data marketplace and centralizing all of its data into “one single source of truth,” as he put it. In his organization, digital tools and data were just enablers, and the real progress hinged on having a digitally dexterous workforce. Naturally, that took longer to develop (and the work continues to this day). He had to be in it for the long haul; after all, digital dexterity is a marathon, not a sprint.
For this leader, sustaining a long-term commitment meant embedding the digital strategy into the daily operations and long-term talent strategy of the organization. A decade into the journey, the corporate business strategy was revised to reflect that digital tools and data would become distributed throughout the organization and become a part of the work itself rather than reside in a separate cost center of excellence. Under the new strategy, “there was no mention of AI or digital transformation,” one member of the leadership team told us. “It’s just assumed now.”
As digital became more integrated, the leader also ensured that training and upskilling opportunities for talent development were not one and done but continuous. He worked directly with the organization’s HR partner to devise a list of critical skills — one of which was AI as a digital technical capability — that leaders would need in order to drive innovation. We’ve seen more and more companies review their talent management systems to better build an “AI-first culture,” as one executive described it, and define how digital can be infused into long-term talent systems. The leader’s senior team continued prioritizing learning about and experimenting with generative AI in an ethical fashion, testing out their use cases in their company’s sandbox.
Throughout the process of integrating digital, the leader sustained energy and commitment over the long haul by setting milestones along the way, from periodically assessing and celebrating progress to annually supplementing the organization’s engagement survey with a more targeted culture assessment. “Sometimes we need to remind ourselves of how far we’ve come,” one member of the leadership team told us. “We forget the amount of change sometimes.”
Sustaining momentum can also require leaders to draw on external resources and relationships. Our survey data tells us that leaders who are making progress in building enduring digitally dexterous workforces increasingly recognize that to accelerate their transformation, they often have to forge partnerships with outside organizations. These moves tend to happen five or more years into their transformations and are often done to gain access to new digital technologies and valuable external data sources. These leaders acknowledge that collaborating with organizations or teams different from their own (such as legacy companies partnering with startups to pursue a tech solution together) may be challenging, and they may want to wait to do so until their own culture and capabilities reflect the kind of collaborative mindset and behaviors they hope to access on the outside.
Your Leadership Sets the Stage
Leaders continually tell us that they currently face what feels like unprecedented uncertainty and ambiguity. They don’t know what technology or even their jobs will look five years from now. But what they do know is that they will need the right talent to compete. Having a digitally dexterous workforce — one that is ready to apply evolving digital tools and data — has already become table stakes. But the leaders we’ve studied have acknowledged that not all of their employees are going to become digitally dexterous, and some will be replaced by technology. Some leaders reported “early retirements” and “rightsizing” at their organizations.
In 2024, 80% of leaders surveyed told us that they thought the benefits of generative AI would be complementary, while 20% of leaders said they thought it would be substitutive. In just one year, our survey results changed drastically: In 2025, 53% of participants reported that they thought generative AI would be complementary, while 43% thought it would be substitutive (and 4% reported that they thought there would be no change).
Leaders who have made more progress with digital dexterity have reminded us that organizations take on their leader’s mindset, values, and behaviors. If leaders want to build a digitally dexterous workforce themselves, they have to look at what kinds of behaviors and values they are radiating, as one executive told us. Are they upskilling and reskilling themselves, making opportunities to get their hands dirty, and learning all about the next emerging digital tool? Are they sending consistent signals through their rhetoric and actions to encourage their people to be nimble in the face of continual technological change? Are they building bridges between people within their organization while remaining empathetic and inclusive of diverse perspectives? Are they enabling reinvention by staying curious, committing to continuous learning, and adapting to change along the way?
We’ve seen firsthand that for leaders who make more progress than others in digital transformation, it’s not just about what they do but how they do it. Leaders are now tasked with “unlearning” and “deconstructing” themselves to “make room for a new form of leadership,” one Asia-Pacific executive said to us. “We must change the way we work and lead.”
The future belongs to you. Now is the time to reframe the challenge ahead, engage from the top, bridge people and perspectives, and sustain long-term commitment.
