Training Upwards: Why CEOs and Executives Must Learn Digital Skills to Stay Competitive

Do your executives fully understand digital transformation? Even your CIO and CTO may need refreshed skills. New studies show that it may be just as critical to provide technology and digital skills training to top executives as it is to line workers. There has been plenty of discussion about the need to provide training to workers to acquaint them with digital skills. Some high-profile companies, such as Amazon, have committed almost a billion dollars to bring their workforces up to speed with digital and artificial intelligence skills. Worker training is a necessity these days, but for many technology managers and professionals, there’s an equally pressing need to train upward in the ranks.

While it can be assumed that most of today’s executives understand the need to accelerate digitally to remain competitive, many simply don’t know what goes into making this a reality. “Successfully navigating this digital acceleration requires a shift and expansion of responsibilities across all roles throughout the organization,” Cheng and her co-authors conclude.

Since these decision-makers control the budgets that can deliver or support digital capabilities, they must be familiar with the challenges and benefits of technology. Let’s face it, corporate leaders are leaning heavily on their technology teams to guide them through the disruptions that are flattening entire industries and upending their relationships with customers. As part of this, it’s incumbent upon technology professionals to provide education along with that guidance.

Digital or technology savviness is not a top requirement for executive or board-level jobs, a recent study published in the Harvard Business Review finds. A review of executive search listings shows that while high-focus roles such as CIO and CTO mention “technology” or “digital” skills as part of their criteria, this drops to 60% for CEO listings, 40% for COO, CFO, and board listings, and 30% for HR leaders. The researchers, led by J. Yo-Jud Cheng, conducted an analysis of more than 100 search specifications for C-suite positions in Fortune 1000 companies across a broad range of industries, posted between January 2016 and June 2020.

Most companies focused on just a subset of job roles in their digital transformation efforts, indicating that many had not been taking a broad enough approach in revamping their talent. The coming months and years will be turbulent in terms of management turnover driven by digital knowledge and skills requirements, Cheng and her co-authors predict. “The pandemic has exposed the executives who were not up to the challenge of a rapid technological pivot. Once boards and top teams have time to search for new candidates and more candidates are unleashed into the external market after annual bonuses are disbursed, we will likely see tremendous amounts of turnover and a very turbulent environment that will highlight the chasm between the digitally savvy haves and the traditional have-nots.”

The top skills needed in the C-suite include design thinking, artificial intelligence, data science, machine learning techniques, cybersecurity, and DevOps, according to a 2019 study from Gartner. With the rise of the digital economy, “the demand for digital savviness in the upper echelons of leadership has grown far more quickly than the supply,” another study published in MIT Sloan Management Review confirms. An analysis of almost 2,000 large companies found that only seven percent have digitally savvy executive teams. Even more surprising, only 47% of CTOs and 45% of CIOs could be considered “digitally savvy.” This percentage drops to 24% for COOs and 23% for CEOs. Only 12% of CFOs were up to speed digitally.

The MIT Sloan team, led by Peter Weill, identified 251 keywords and phrases that describe a digitally savvy executive from almost 17,000 executive biographies, applying natural language processing techniques. The digitally savvy executives actively support IT practices that are “modular, open, and agile,” Weill and his co-author report. “Leading companies use application programming interfaces (APIs) to transform their ‘crown jewels’ (what they already do best) into digital services that can be tapped internally for innovation and externally by partners to create ecosystem value. For instance, at the companies in the top quartile of our study, more than half of core capabilities are enabled by APIs, compared with 19% at bottom-quartile companies.” Automated decision-making and encouraging rapid learning also characterize organizations that promote digital skills in their leadership.

Whether you are in the leadership ranks, aspire to be, or are immersed in the technology side of things, you need to engage in bringing technology and digital skills development to your corporate leadership team. The researchers provide several steps that need to be taken to mold corporate leaders and boards into more digitally savvy participants:

• Assess executives’ current level of digital savviness. “The CEO, chief human resources officer, and the CIO need to have a frank discussion,” say Weill and his co-authors. “This conversation should identify the digitally savvy executives on the team and, by extension, those lacking this capability.”
• Reverse mentor. “Learn from the people who are ahead and the people who are behind you,” Cheng and her team advise. “There is much to learn from the people who are closest to new technologies and customers.”
• Strengthen key members first. “The leaders of this effort should first focus on strengthening the digital savviness of the executives occupying the key roles of CEO, CFO, head of marketing, head of corporate communications and investor relations, and head of compliance and legal,” Weill and his co-authors recommend. “If the CEO is not yet digitally savvy, this is the logical place to start. After all, it is CEOs who lead companies to new ways of doing business, changing the organizational culture and reorganizing the company to take full advantage of new technologies.”
• Seek out development and rotation opportunities. This helps “build out your existing digital and leadership capabilities,” Cheng and her team state. “Be willing to take lateral moves to develop new ones. Even if these changes do not provide an immediate promotion, they will offer valuable experience that will round out your qualifications.”

Digital transformation is no longer a choice but a necessity for organizations striving to remain competitive and relevant. However, true transformation goes beyond technology; it requires visionary leadership that understands and embraces digital capabilities. Building digital literacy among executives ensures that strategic decisions are informed, agile, and forward-looking. As technology continues to evolve, companies that invest in developing digitally savvy leaders will not only navigate disruption successfully but also pioneer innovation in their industries.