The Disconnect Between Legacy Executives Vs Digital Enablers in Today’s Business Realities
In the rapidly evolving digital landscape, the traditional, legacy role of the Executive is being scrutinized and challenged. As digital transformation initiatives continue to falter, with failure rates hovering around 75%⁹, the need for a new breed of leadership — termed digital era enablers — is becoming increasingly apparent. Having been in the IT industry since the 1990s, I have personally witnessed this growing disconnect between the industrial and digital mindset. Legacy executives, by and large, focus on lofty strategies, buzzwords, and playing the “role” without meaningful impact on the way workers use technology to be productive. Yet if there’s no tangible return on investment in worker productivity and digital technology, the workers are usually to blame. Then comes the kinds of layoffs that Wall Street investors enjoy, without any proof employees were truly the problem.
Often, these workers have no standing to call out this executive antipattern. But let’s not leave out those on the board of directors who choose CEOs, and key investors who tend to be hands on in micromanaging c level executives. They are all “executive actors” who need to look in the mirror and hold themselves accountable for failing to lead organizations from the industrial mindset into the digital mindset.
In this year of the reckoning, time’s up for all stakeholders, not just employees. Even now, cloud adoption and migration projects are exhibiting the same classic leadership and vision antipatterns that lead to most digital transformation initiatives failing. Most leaders pay lip service to “agile management,” “platform engineering”, “DevOps,” “Generative AI,” and so on, but really don’t know the pulse of sprint and product teams.
But when you put a microscope on each project, including those pretending to be “sprints,” what you find is the same old “fly by the seat of your pants” wild wild west approach to projects. Ill formed teams through everything but the kitchen sink at the problem to hope for a miracle solution to pop up magically out of thin air. A few heroes do the bulk of the work while others, due to lack of proper team planning, sit around and watch. Burnout occurs, and finger pointing results. Yet no one dares blames executives. More teams are falling into this poor choice of project structure unintentionally.
One might label this “waterfall.” I wouldn’t even offend waterfall methodologists here, because at least waterfall projects have structured requirements and certain logical and physical diagrams. What I keep seeing are executives under pressure from their c level executives or boards of directors to do impossible ambitions in shorter periods of time without regard to work life balance and encouraging innovation. This is especially true in the U.S.
Project teams are not properly staffed at the right time during the quarter or sprint. Teams often lack true story writers, resulting in badly formed requirements that make little to no sense to architects and developers. This, in turn, leads architects to guess at the requirements, which the confuses developers. Under tight deadlines, developers have no choice but to guess at the detailed design for the code. Bugs, failures and code rewriting are the outcome.
And who gets blamed? Either the architects or developers. Never mind the organization did not want to hire Business Analysts with user story writing skills who can also write features and epics. Never mind they are not sold on the importance of architecture runways for nonfunctional requirements and “business as usual” (BAU) enabler epics. Setting aside these very important elements of a successful digital transformation project will result in the kinds of failures that Gartner Group and McKinsey & Co pointed out in their related reports.
It is long past time to put to pasture the antiquated notion of the executive, which has old roots in the robber baron era of the Industrial Revolution of the late 1800s. They served their purpose, bringing society from being a predominantly agrarian culture to an industrial and officer working one. During this time period, executives pretty much relied on cracking the whip on employees to get results for investors. Evolution in management philosophies such as those promoted by the late father of modern management, Peter Drucker (with whom I enjoyed a brief mail correspondence until he passed) improved the guardrails for how executives managed employees. However, the DNA of the legacy executive mindset persisted, and reared its ugly head when investors got impatient with “strategies” and “value chain management” at the c suite level. When they wanted money, executives had to jump and squeeze workers, just like their industrial era predecessors always reverted back to when the pressure was on.
But then came the digital revolution that changed everything. Leadership now requires enablers, not executives. The industrial era executive became obsolete overnight and didn’t even realize it. So let’s explore this disconnect between “Legacy Executives” and “Digital Enablers.”
“Legacy Executives” and “Digital Enablers”
Legacy executives, often selected by boards and major investors for their ability to deliver investor-friendly sound bites and buzzwords, are frequently out of touch with the operational realities of digital transformation. These leaders tend to focus on high-level strategic visions that look good in business journals but fail to address the practical challenges faced by their organizations⁹. This disconnect is particularly evident in their lack of engagement with portfolio backlogs, which serve as the digital diary of an organization, capturing the essential epics and initiatives that drive business value⁵.
Digital Enablers live by what’s in the backlogs. Think about it: When in the history of business have leaders had perfect, hierarchy driven access to the pulse of their employees at the Portfolio, Product and Sprint level? There is no other critical business tool than that modern backlog. There’s even a Retrospective at the end of each sprint that tells you how each sprint team member feels about their progress, and how they plan to improve for the next sprint.
Side Note: Regular sprint retrospectives help the team identify and address issues early, allowing for adjustments to the plan and priorities. This mitigates the risk of significant problems arising from taking shortcuts. Periodically reviewing these retrospectives without the old school executive mindset provides excellent insight into worker productivity and motivation at the most granular level. An Enabler can use this info to help sprint teams improve by removing obstacles and empowering them with accurate, relevant info, not strategic buzzwords and corporate psychobabble spoken in online town hall meetings.
No executive dashboard can deliver this much insight into the worker mindset as the backlog and the retrospective. This is where worker productivity lives, deep in the backlog.
The Role of Portfolio Backlogs
The portfolio backlog is a critical tool for aligning digital initiatives with strategic business goals. It provides visibility into the work that needs to be done, ensuring that all stakeholders are on the same page and that initiatives are prioritized based on their potential impact⁵. Effective management of the portfolio backlog is essential for maintaining organizational agility and responsiveness, especially in large, complex environments⁶.
I can’t be more clear hear. In the industrial era of management, this deep level of visibility into the inner workings of every business process in the organization was unheard of. It was mostly hypothetical guesswork with some business management science sprinkled here and there to appease investors. It ALL goes down in the backlogs. Organizational leaders need to dive in and check the judgmental attitude at the door. Let the worker speak through the backlog.
Economic Pressures and the Urgency for Change
With economic downturns looming, corporate budgets are expected to tighten over the next 4 to 6 quarters¹⁶. This creates additional pressure on organizations to adapt quickly or risk falling behind those that have already embraced successful digital transformation initiatives. The contraction of capital expenditure (capex) budgets will necessitate a more strategic approach to digital investments, further highlighting the need for leaders who understand the intricacies of digital transformation¹⁶.
The Emergence of Digital Era Enablers
Digital era enablers are leaders who possess a deep understanding of digital technologies and their strategic applications. They are agile, adaptable, and capable of empowering teams with the right tools and fostering a culture of continuous learning and innovation¹. Unlike their traditional, legacy counterparts, these modern leaders are actively involved in backlog management, ensuring that digital initiatives are aligned with strategic goals and effectively prioritized⁵. Not grasping this critical concept will doom every digital transformation and cloud adoption initiative.
The Importance of Soft Skills
Convincing legacy executives and their sponsors to embrace new digital realities requires a nuanced approach that emphasizes soft skills. The promise of increased profitability through digital transformation should be enough motivation to introduce sweeping changes among the executive and investor mindset, but the lack of self-awareness in the c suites and their investors is still pervasive. Therefore, some hand holding and coddling is needed.
Empathy, effective communication, and strategic persuasion are essential for bridging the gap between high-level strategic visions and operational execution¹⁹. By leveraging these skills, digital era enablers can create a sense of urgency and demonstrate the tangible benefits of digital transformation, even in challenging economic times¹⁹.
Conclusion
The shift from industrial era executives to digital era enablers is not just a theoretical concept but a practical, existential necessity for organizations aiming to succeed in the digital age. The clock is ticking. The world is moving at the speed of digital, not analog, business. As economic pressures mount and the pace of technological change accelerates, the need for leaders — Enablers — who can navigate the complexities of digital transformation has never been greater. Embracing this new leadership paradigm could be the key to overcoming the persistent challenges that have plagued digital transformation initiatives and driving sustainable growth in the digital era.
Time to transform industrial executives into digital enablers, which is not a trivial paradigm shift. If your organization needs help putting the backlog and architecture runway into practical use in a way that maximizes return on capex investment, reach out to me today on this platform or at www.SamsonaSoftware.com.
¹: [Deloitte Insights](https://www2.deloitte.com/us/en/insights/topics/strategy/leadership-in-digital-transformation.html)
⁵: [Scaled Agile Framework](https://scaledagileframework.com/portfolio-backlog/)
⁶: [Agile Alliance](https://www.agilealliance.org/resources/experience-reports/organization-business-agility-managing-portfolio-backlog-large-organizations/)
⁹: [McKinsey](https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/unlocking-success-in-digital-transformations)
¹⁶: [Technology Magazine](https://technologymagazine.com/articles/concerns-recession-will-slow-digital-transformation-progress)
¹⁹: [TechRadar Pro](https://www.techradar.com/news/why-soft-skills-are-critical-to-digital-transformation)
Source: Conversation with Copilot, 7/17/2024
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