Posted: 10 Jul. 2020 5 min. read

Helping increase the odds of leadership success in digital transformation

Posted by Erin Clark and Wayne Robinson on July 10, 2020.

Most organizations understand that to be competitive in the market, they need to invest in digital transformation. However, organizations often underestimate the importance of cultivating leaders who can drive the required change. Many digital transformations fail due to unprepared leaders. How can you better ensure that your organization has the right leaders with the skillset to successfully lead a digital transformation? How do you prepare and form teams that have the skills and problem solving to be successful in a transformation? There are four key principles to support executing a successful transformation: pick the right leaders, build high-performing teams, find new ways to solve new problems, and embrace a growth mindset.

Pick the right leaders

A common pitfall for many organizations embarking on a digital transformation journey is the assumption that the effort should be led by the people closest to the work that is being transformed. On the contrary, closeness to the work may actually be limiting. Transformations are messy and fraught with change, uncertainty, and risk. Leaders of the effort need to be more comfortable navigating these dynamics than they need to be skilled in a particular discipline. In fact, while those closest to the work may be the easiest choice or the choice that seems to make the most sense, they may also pose the greatest risk. Organizations should take time for due diligence when selecting or hiring an executive sponsor or project leader. This appraisal should include an assessment of a leader’s transformational leadership capabilities rather than functional expertise.

Things to look for should include leaders who are comfortable and capable of:

  • Anticipating the future across the organization
  • Seeing past their own business unit or functional area and engaging in partnerships across the organization
  • Constructing a clear case for change, communicating its value to a variety of audiences, and leading by example
  • Tackling complex opportunities and challenges and possessing a growth mindset

This assessment may end up confirming that some of those closest to the work are a good fit, but it will also confirm the selection is made for the right reasons, focused on the fit for transformation rather than technical skills or experience.

Case in point: A global manufacturing company embarking on a digital transformation originally aligned its IT department to lead the development of new digital customer interfaces and order tracking and management tools. Eighteen months into the process, it became clear that while expertly capable of leading the development of a new, functional tool, this leader had never implemented such a broad-reaching and systemic change. Spending the time and money upfront to assess for these capabilities and aligning a true transformation leader from the start would likely have saved even more time and money—and led to a successful outcome.

Actively and intentionally build high-performing teams

Digital transformations bring new opportunities and new challenges that often necessitate changes in team structure and roles. Leaders should assess the health of an existing team, or build a new one, by focusing on the outcomes they are expected to create for the future, rather than past performance. Once configured, leaders must continuously shape the dynamics of high-performance for the team by providing clarity, assuring capacity, and cultivating commitment. 

Leaders provide clarity for teams by aligning on purpose, team roles, and governance as well as in establishing the right mode and rhythm of interactions for the team. While the purpose and desired outcomes may be clear, the path to get there is likely not. Clarity on purpose and effective functioning of the team will serve as an anchor in the face of the uncertainty they will face.

Leaders assure the capacity of their teams to achieve desired outcomes by intentionally balancing capability and workload, making adjustments to rebalance as needed. But assuring capacity also means providing the right enabling technologies and tools to support coordination, collaboration, efficient process, and knowledge management. With teams operating in virtual or mixed environments and often across geographies, both practices to assure capacity are critical to high-performance.

Leaders cultivate commitment for teams by empowering teams and their members to grow and feel a sense of belonging—both to the team and to its purpose. This requires being both visible and vulnerable to intentionally establish an inclusive team culture where members feel comfortable and connected to one another.  And, it means recognizing the contributions that are being made to the work of the team by individual team members. These actions can build trust and cultivate the mutual commitment needed to sustain high-performance on the transformation journey.

Case in point: At the outset of a digital transformation, ABC Co. decided to bring all the leaders of its primary initiatives together for a ‘kick-off’ event. On reviewing the agenda, the CEO bristled at the half-day devoted to “that soft stuff” focused on enabling leaders to build high-performing teams. Fortunately, the chief digital officer—leader of the transformation, insisted and the agenda remained. In a poll of leaders six months following this event, the sessions were identified as the most helpful in preparing them to lead. And, the materials and toolkits from that session were among the most referenced throughout the project.

Breakaway from your problem-solving routine

Transformational work by its very nature is work that has not been done before and will likely not fit traditional problem-solving frameworks. Digital transformation means challenging the status quo, developing and scaling new technologies, shifting operational mindsets, and adopting new behaviors. It would be naïve to think that the same ways of working that have brought past success will work when trying to transform the business. Not only should the business transform, but the ways of working, thinking, and problem-solving should transform as well. This is important for both leaders and team members—organizations should prepare their leaders so that those leaders can in turn prepare and coach their teams in adopting a new problem-solving philosophy. One in which leaders and their teams embrace the uncertainty inherent in the world around them, managing it through outside-in and scenario thinking; one in which leaders and their teams push beyond what they know through divergent rather than convergent thinking; and one that is inclusive of new or different ways of working, thinking and being and invites everyone to be at their best.

Case in point: A global construction and building materials company that had embraced agile development in its IT department recognized the opportunity of doing so more broadly and transformed its leadership development programs to evangelize the philosophy, tools, and methods in its mid-career and high-potential leaders.

Embrace a growth mindset—never stop blowing on the spark

The context of a digital transformation is anything but constant and may well be described as a journey of exploration, learning, and adaptation. Big, bold moves may be warranted but doing so predicated by a path of smaller incremental learning steps will keep things moving on a path of success. This may seem to fly in the face of the popular corporate slogans about embracing failure for its learning value and while the underlying philosophy may be the same, we’d like to propose that transformation leaders embrace the learning rather than the failure in that equation with a growth mindset.  

Our colleagues, Geoff Tuff and Steve Goldbach do just that in their recent book Detonate, in which they advocate an orientation of minimum viable moves through which we learn and adapt vs. placing big bets couched in a high degree of uncertainty and the prospect of failure something to celebrate. Similarly, one of the traits in our digital DNA framework is “Fail Fast, Learn Faster”—which on the surface may seem more similar to the embracing failure philosophy, but in practice is more aligned to minimum viable moves and a learning-based growth mindset: We say that being digital means that experimentation, iterating and ‘always on’ learning is baked into our success.

Cultivating a growth mindset in your leaders is critical to sustaining the forward progress of the transformation. Moreover, these leaders will also need coaching strategies and other resources to cascade this mindset into their work and that of their teams—to go from a “you just don’t get it” mentality to a “we may not get it, yet . . . but we will” mindset.

Case in point: Anxious to embrace a growth mindset at all levels in the organization, one organization implemented the practice of beginning every meeting with a “learning moment” in which the leader or someone they invited would share a brief anecdote of something they had learned that had changed their behavior or improved their ability to create value—at work or in life, more broadly. The focus on learning in every meeting helped set a tone of growth well beyond just those directly involved in the transformation initiatives.

Developing leaders for digital transformation doesn’t happen by accident

Organizations that prioritize the capabilities and influence of their leaders when setting out on a digital transformation are more likely to succeed. By taking the time to develop and choose the right leaders, you can meaningfully reduce your risk of failure. Infuse your leaders with the capabilities they require today and foster the growth of future leaders who can take on the more complex and demanding responsibilities that are required in a rapidly changing market—beyond the work of the transformation itself.

Deloitte provides solutions to support the identification and development of transformation leaders:

  • Leader assessments: Leveraging a combination of proprietary tools, integrated with your existing leadership models and frameworks to build a robust view of your leadership talent, specific to the capabilities required to lead in digital transformation.
  • Team assessment/composition: Leveraging our proprietary Business Chemistry and Team Alchemy methodologies, tools, and resources to identify areas of opportunity and risk.
  • Individual and team coaching: Targeted coaching for individuals and teams to address specific areas of opportunity.
  • Individual and team development experiences:
    • Bring Your Own Challenge (BYOC) Workshops: Through the BYOC methodology, leaders obtain a framework for solving real business problems in an agile fashion and develop a mindset that better allows them to solve complex problems today and in the future (delivered live or virtually)
    • THRIVE Leadership Experience: A digitally enabled development experience to accelerate leaders’ ability to lead in uncertain contexts, leveraging a ‘learning in the flow of work’ philosophy in which the real work of the participant is the forum for building new capabilities.
    • Fully Customized Experiences: We will work with you to design an experience that is contextualized to the reality of your transformation.



Erin Clark is a managing director with Deloitte Consulting, Human Capital. She has more than 20 years of experience working with clients to improve their performance, drive change, and create sustainable advantage through people.

Wayne Robinson is a specialist leader in Deloitte’s Learning and Leadership practice. He has more than two decades of experience developing leaders in very dynamic environments.

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