Digital transformation programmes do not typically fail because of strategy – they fail in execution.
A 2024 study by Boston Consulting Group found that more than two-thirds of such programmes are not delivered on time, within budget or to scope. This figure has remained largely unchanged for nearly a decade.
For large organisations, the cost of failure can exceed €20 million annually for a single programme.
As Mr Khoong Chan Meng, CEO of NUS-ISS, observes: "Most organisations do not lack strategy. Their challenges are often with the capability to sustain execution of strategy at scale, while situational decision making continues to be required on a daily basis across teams, systems, and stakeholders. Imagine rebuilding an airplane while it is still flying, with passengers on it."
So where does the breakdown happen?
In many cases, it happens in what can be described as the execution layer, the critical middle where strategy is translated into delivery.
The overlooked layer where transformation succeeds or fails
At the heart of this gap are people.
Specifically, the managers responsible for turning direction into outcomes, making decisions on vendors, data readiness, delivery timelines, and stakeholder alignment. These are not abstract responsibilities. They are practical, high-stakes decisions made daily.
Yet many step into these roles without formal preparation for the complexity they are expected to navigate. In the UK, as many as 82% of managers report receiving no formal management training.
Transformation does not typically fail in a single moment. It fails quietly through a series of small, compounding decisions at this execution layer.
Approving vendor contracts without fully understanding exit clauses, leading to arrangements that no longer serve the organisation
Launching AI initiatives without addressing fragmented or unstructured data, resulting in stalled projects before they begin
Migrating platforms without mapping downstream dependencies, creating hidden costs, retraining needs, and operational disruption
Many managers learn these lessons on the job, eventually. But when learning happens this way, the cost is borne not by the individual, but by the organisation.
At the same time, these managers operate under constant tension. They are expected to move quickly and innovate, while ensuring systems remain stable, secure, and compliant. Navigating this balance requires more than experience. It requires deliberate capability.
Closing the execution gap
Organisations have traditionally invested heavily in two areas: senior leadership and technical expertise.
But the execution layer, the bridge between strategy and delivery, often receives far less structured attention.
Organisations that execute well tend to build five core capabilities in this layer:1. People and communication
The ability to lead teams, manage performance, and influence across functions. This includes translating between technical and non-technical stakeholders.
2. Execution and delivery at scale
Driving outcomes across interconnected systems and teams, often without direct authority, through disciplined delivery and change leadership.
3. Business and commercial acumen
Making sound decisions on budgets, vendor contracts, and build-versus-buy trade-offs where technology meets commercial reality.
4. Customer and outcome orientation
Defining the right problems before pursuing solutions, and measuring success based on impact, not just delivery milestones.
5. Data, AI literacy and governance awareness
Not deep technical expertise, but sufficient understanding to evaluate proposals, assess risks, and make informed trade-offs in areas such as security, resilience, and modernisation.
These capabilities enable managers to operate with judgement, especially in domains where they are not the technical expert.
Developing managers who deliver
Some organisations have recognised this gap and act on it deliberately.
They invest in developing their execution layer through structured programmes, targeted education, coaching, and shared operating practices that reinforce day-to-day execution. Initiatives such as Google’s Project Oxygen demonstrate that effective management is not incidental. It can be systematically built and scaled.
For organisations looking to strengthen execution, the starting point is straightforward:
Assess the current capabilities of managers at this layer
Identify where gaps exist
Close them through structured development and applied learning
Equally important is closing the loop by embedding these capabilities into how performance is measured, how careers are developed, and how leaders are promoted.
Because what organisations measure, they prioritise.
From strategy to sustained outcomes
What distinguishes organisations that execute well is not simply an awareness of the problem, but a decision to address it systematically by investing in the layer where execution actually happens.
For professionals operating in this space, the challenge is equally clear. To move beyond managing tasks and towards making sound, informed decisions that translate strategy into sustained outcomes.
The Master of Science in Enterprise Digital Technology Management (EDTM) at NUS-ISS is designed with this in mind. It focuses on equipping managers at the execution layer with the capabilities required to navigate complexity, make trade-offs with confidence, and deliver results across functions and systems.
With a modular structure, professionals can address specific capability gaps through individual graduate certificates, or pursue the full Master’s pathway for comprehensive development. The full Master’s programme will be launched in early 2027. For enquiries, please email: iss-admissions@nus.edu.sg
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This thought leadership article is contributed by Ms Nadine Yap, Principal Lecturer & Consultant, Digital Products & Platforms Practice, NUS-ISS who shares her perspectives on the topic.
Nadine Yap is a Principal Lecturer for the Digital Products and Platforms Practice at NUS-ISS. She has over 25 years of experience in the digital media industry, where she has successfully delivered results in all aspects of product strategy development, product life cycle management, team leadership and international product execution.
Most recently she was the Chief Product and Technology Officer at The Parent Inc, Southeast Asia's largest parenting platform. Her experience spans general management, customer success, product marketing, product operations and digital transformation, from b2C products such as Viki.com, Yahoo.com and Amazon.com, as well as B2B Infrastructure as a Service Companies such as Temasys, and Non-Profits such as the Law Society of Singapore, Pro Bono Services Unit. She has worked in the US and Singapore, with globally distributed teams and clients.
Nadine has a Bachelor of Arts in Sociology, a Master of Arts in Regional Studies East Asia, both from Harvard University, and became a software engineer soon after graduation, by teaching herself how to code and asking lots of questions.