Top 10 Leadership Challenges in Digital Transformation Era

Leadership in the era of Digital Transformation is not for the faint of heart. Leadership must be innovative, disruptive, transformative, transparent, and more. Business challenges become more intense, scrutinized, and challenging to overcome. Through my many years of experience in leadership roles in business and digital transformation, I can tell you that the transformation road is never straight but zigzagged in unexpected ways. Reframing a definition of success is the first skill a leader needs to master!

What specific challenges can derail even a seasoned executive?

  1. Speed to market
  2. Ever-changing and multiplying technology stacks
  3. Archaic or monolithic architecture, aging tech debt
  4. Swift pivots to new market opportunities
  5. Agile development in the highly distributed global landscape
  6. Clash of a surplus of development methodologies
  7. Talent deficit across many technical disciplines
  8. An expectation to create a unique knowledge worker culture
  9. Employee engagement issues of a highly mobile and employable employee-base
  10. The Great Resignation

What do these challenges mean for the companies and their leaders?

The speed required in the innovation process does not always match companies’ operational maturity and ability to scale and deliver. Repeatable innovation with predictable delivery continues to be a goal for many companies. Organizations must understand that the road to repeatable processes and predictable delivery is complex. And those who master the process should celebrate!

Technology companies and IT departments face a constant barrage of new technology.  New tools and technologies allow companies to swiftly solve their business problems and modernize technical solutions. However, teams are rarely given a chanceto sunset old technology or refactor thoroughly and adequately. This means integrating new tools and solutions adds additional complexity and often hinders teams’ ability to navigate their complex technology ecosystem.

Since innovation is progressing faster than ever, it also means that technologies and solutions are agingat alarming rates. Professionals are expected to quickly adapt to new philosophies, software development methodologies, architecture and development frameworks, programming languages, standards, and protocols. This is another reality that often negatively impacts a team’s delivery ability. They are expected to decrease go-to-market time frames while meeting customer demands, innovating new solutions, and managing backlogs while inheriting outdated programs.

The benefits of globalization are huge, but the pains and inefficiencies introduced by globalization are rarely discussed. Technology delivery is a team sport! This cannot be easy when teams are distributed globally. In addition to their tasks, they must manage time zones, language barriers, customs, and more. Collaboration tools have positively impacted how teams work, but communication, clear strategy, solid planning, well-orchestrated execution, team alignment, and trust are genuine challenges that take years to overcome. There are no shortcuts to getting better results.

Despite all challenges with the digital transformation processes and technologies, the hardest to solve are human capital challenges. Knowledge workers are employees with unique needs, expectations, and experiences. These are highly trained professionals that are in demand in today’s market. The cultural norms and expectations of “office perks” continue to increase. From snack, game rooms, and ping pong tables to WFH (or more like work from anywhere in the world) to continuing L&D investments and team bonding experiences. Companies must stay in tune with their organizations’ needs and evolving cultural norms (and their competitor’s organizations). As a rule, the companies that do not create a clear strategy to treat their employees as critical assets have no chance of winning the talent war!

As you can see, leaders in companies delivering digital transformation have a lot they need to focus on and solve. There is significant stress and pressure on executives working in private equity-owned companies. Value Creation is King in Private Equity. Leaders are expected to demonstrate ingenuity, an entrepreneurial approach to problems and solutions, agility in decision making, and flexibility to adjust to new opportunities at a moment’s notice. They are constantly assessed for their ability to define a clear business strategy, achieve ambitious business results, and effectively lead their teams.

What leaders must do to thrive in Digital Transformation

  1. Invest in yourself to reach your limitless potential
    1. Find a mentor, a sounding board, and a trusted advisor
    2. Zero in on your leadership skills, get frank feedback where you can be more effective
    3. Focus on what you can positively influence in your ecosystem
    4. Embrace the power of relationships with your peers, your team your superiors
  2. Invest in your leadership teams’ limitless potential
    1. Focus on trust development and team alignment
    2. Establish high functioning team mentality
    3. Lead by example in the mission of operational excellence
  3. Invest in your organization’s limitless potential
    1. Create a culture of belonging, loyalty, and commitment
  4. Give your organization resources that will make them more marketable
  5. Treat your people as your most critical assets

Leadership responsibilities in the Digital Transformation space can be frustrating. My best advice on being more effective is to focus on what you have in your control and what you can improve within yourself. Create an active support network, including trusted advisors, mentors, and peers. Leading by example never fails!