Digital transformation has become the mantra of the modern enterprise, a promised quick fix to inefficiencies and problems, while simultaneously delivering unprecedented growth. One thing you’re always taught from a young age is that change often comes hand in hand with time. The faster something happens, the worse the results will probably be. Beneath the false optimism of transformation lies a sobering truth: most digital transformations are doomed to fail, at least relative to expectations.
The paradox is quite striking; we live in a world of unparalleled digital advancements, technology being the most accessible and agile it has ever been, and yet, most businesses fail in their reformations.
Eric Veldboer, CEO and co-founder of CBOS, brings over 35 years of international experience in technology leadership across both corporate and entrepreneurial spheres. Having served as CIO, CTO, and CEO in major organisations, and founded multiple successful tech start-ups in the UK and the USA. He describes the problem quite succinctly:
“Transformation doesn’t fail because the tools we’ve built are wrong for the company, but rather because the purpose for the technology is unclear. Software can’t compensate for the lack of intent.”
When the purpose of transformation is poorly defined, technology becomes a symptom of confusion rather than a cure for it.
The Illusion of Progress
With transformation often comes the subsequent enthusiasm of ‘the new shiny thing’. However, as the saying goes, “You can’t polish a turd, but you can roll it in glitter”. While the new technology certainly makes the old workflows look better, it doesn’t magically fix the inefficiencies. Technology isn’t a magic syrup; it’s a tool, you can automate without improving, digitise without clarifying, and accelerate without direction. It all relies on the underlying systems in place. The organisation may become faster but not necessarily better.
The failure to progress stems from a simple and yet devastating oversight; the transformation starts with the means, while never understanding the intricacies of the end. Projects are scoped around the tools themselves rather than articulating the goals to be achieved with these tools first.
What business problem is being solved? To deliver any sort of effective or meaningful change from digital transformation, this is the question that needs to be answered first. Is the aim to reduce headcount through automation, or eliminate error rates through a single set of unified data, or to accelerate turnaround time across departments? Clarity of purpose should precede everything else. Once there is an understanding of what the technology is for, it can be utilised in its most effective manner.
As Eric notes, “You can’t measure success if you don’t define it. A system has no inherent value unless it makes the business measurably better.”
Transformation without defined outcomes is a performance without a script; at some point, the improvisation fails and with it the transformation.
From Technology to Strategy
The most common misconception in a transformation of this kind is that it is primarily a technical endeavour. In reality, it is a strategic one.
Technology isn’t the destination in and of itself; once it has been implemented, it doesn’t just run alone. When the initiative to revolutionise is separate from the broader business strategy, it loses coherence and direction. The transformation needs to be linked to something clear; the creation of a new product or expanding into new markets, not just to a broad strategy of “modernising operations” or “refreshing technology”. The fact that the strategy is defined unambiguously means that the correct steps can be put into place to implement the new systems.
“Every implementation should express strategy. Technology is not separate from the business.”
This is not something a company has to do alone; any software company worth its salt will be an intimate part of the process of implementation, deploying the software where it adds real value, integrated into the correct processes, and supported by training for the correct people within the business.
The successful examples of this treat the digital infrastructure as an extension of their competitive vision rather than as separate from it.
Defining Success
Without measurement, the progress achieved by the transformation is indistinguishable from what the business looked like before. The hallmark of a mature transformation initiative is not its complexity but its measurability. Clear, quantifiable objectives show where the process is working and how effectively the goals have been achieved.
Eric illustrates this, “You don’t know if something is a success if you can’t measure it. Set some KPIs upfront; we will reduce error rates by 80% or we will reduce headcount by 10 people. This is actually measurable to see if the project was successful.”
These metrics are not bureaucratic details; they are the feedback loops that ensure intent translates into impact.
With measurement also comes transparency. There will be no boardroom arguments (well, fewer, there can never be none) about the effectiveness of the transformation when its effectiveness has been tracked. When success is defined, the conversions shift from opinion to evidence. This fosters collaboration instead of debates, instead of arguments about its effectiveness, teams work together to achieve better measured results.
Governance as Architecture
A transformation that is ungoverned is bound to fail. Technology cannot be treated as a pick-and-place kind of system. There needs to be a structure around it with all the stakeholders taking part and playing a role in the implementation of the technology. It demands a framework that integrates leadership, management, and execution into a single structure of communication and use.
A successful governance model acts like scaffolding for a building; it provides the necessary stability and structure while allowing the work to take place underneath. Within it, there should be a clear structure of who is responsible for what, defined responsibilities, and when to escalate for resolution. Not implementing this step results in the lack of cohesion required for the transformation to take hold.
As Eric describes it, “Governance isn’t red tape; it is more like a nervous system. Without it, information moves too slowly, and the organism fails to respond.”
At CBOS, this structure is built into every implementation. It allows projects to evolve without losing coherence, ensuring that the structure of the business will support the system coming in.
The Speed of Resolution
“Don’t let issues become a roadblock and derail or delay the project. Deal with the issue as soon as possible.”
No transformation is immune to friction. With change comes the inevitable obstacles to the change. Transformation is not about avoiding the existence of obstacles but dealing with them effectively and efficiently. The determinant of success is not the absence of problems but the speed with which they are resolved.
The longer issues sit unresolved, the more they metastasise, consuming time, budget, and morale. Problems must be surfaced early and resolved decisively. This goes hand in hand with governance. If employees and managers are not given the correct roles and structures to deal with these problems, they will fester and eventually cause the downfall of the transformation.
The speed of resolution is directly correlated with the effectiveness of the governance structures.
Phasing: The Discipline of Progress
Large-scale transformations often collapse under their own ambition. There is a natural human desire to have everything delivered immediately, the perfect, all-encompassing solution. But with a greater scope also comes a slower process of implementation.
Any company that offers an immediately working solution is either inexperienced or untruthful, because a phased approach allows for each kink and crease to be ironed out. If these aren’t dealt with during the implementation process months will pass without visible benefit, enthusiasm wanes, and budgets tighten. Stakeholders begin to doubt the project’s direction, and confidence erodes.
The antidote is phasing: the deliberate division of transformation into manageable, outcome-oriented stages.
“Don’t try and achieve the ultimate end-goal in one phase that could take months to fulfil without seeing any real progress or benefit. Small phases with clear benefits deliver value and keep people motivated as they can see progress.”
Each phase must deliver tangible value, something that brings about a visible win and an emotional morale boost. This sustains engagement and provides proof that the vision is achievable.
Furthermore, taking small bite-sized phases allows for a resilient implementation. When changes to the plan come about, as they always do, phases have already been completed. Trying to achieve an implementation in a single phase often means the project, or the process achieved so far, is derailed by a slight shift in objectives.
Managing Scope Without Losing Vision
Transformation is a process; it’s an act of balancing a long-term vision while simultaneously executing short-term steps. Scope creep is inevitable; the challenge lies in managing it constructively.
“Scope changes aren’t failure,” says Eric. “They’re signals. They tell you the organisation is learning to handle the new software.”
When new ideas emerge or problems with workflows persist, they must be tested against the project’s original objectives. If they add measurable value or align with evolving strategy, they should be incorporated into subsequent phases with their own budgets and success metrics. If not, they should be deferred.
Discipline, not rigidity, is the key trait for success. The most successful transformations come from businesses that evolve with the project in a constructive manner, rather than taking the scope growth as a negative sign.
The Human Architecture of Success
Again, it needs to be reiterated that technology is a tool. It cannot create alignment or culture within a business. The most elegant system in the world will fail if the people who use it are unprepared or uninvolved.
True transformation happens when all aspects of a business utilise the tool in a continuous exchange. Each group understands how the system serves their objectives and how their actions feed into its success.
The cultural alignment that comes from this is not accidental, and it’s probably the biggest driver of a piece of software being used and being left untouched. Communication plans, training initiatives, and reporting frameworks must be established early and maintained after the software is live. The value that a business is looking for doesn’t come from paying for a custom solution but from implementing the solution correctly and effectively.
This becomes obvious when the software is no longer noticed, no longer something that is actively encouraged, but a part of everyday work, a necessity of the job.
Preparation and Partnership
No software partner, however capable, can transform an organisation that is unprepared for the transition. The readiness for this is internal.
This requires a clear plan before implementation begins, during the process of implementation, and finally after the implementation has finished. The role of a partner like CBOS is to enable this discipline, to help clients establish the governance structures, define indicators of success, and manage change with precision. But the transformation itself must be owned internally.
“Technology is the easy part,” Eric often reminds clients. “The hard part is alignment, getting people, process, and purpose to move in the same direction.”
Partnership succeeds when accountability is shared, when both the client and the provider see themselves as custodians of the same outcome.
Most digital transformations fail because of a misunderstanding around the intimate role the stakeholders in a company need to play for it to be successful. A piece of software is just that, software. It is not the silver bullet of productivity and efficiency. Yes, it will no doubt increase productivity and efficiency, but it can’t do that without the correct mechanisms in place.
When these conditions are met, technology becomes what it was always meant to be: an amplifier of human intent. “Transformation isn’t about receiving the new software and being on your way,” Eric concludes. “It’s about becoming capable of building new processes.”
In that shift of mentality and understanding lies the difference between the success of a digital transformation and its dismal failure.
- Written and researched by Sean Veldboer, Consultant at CBOS. A big thank you to Eric Veldboer, CEO at CBOS, for the insightful information.
Eric is a highly experienced technology professional with over 35 years’ experience in the Information Technology sector. He is an executive level manager who has performed roles as CIO, CTO, IT Director, Managing Director, CEO and Product Director at both large corporate organizations and smaller organizations, including start-ups.
Eric successfully founded / co-founded two start-ups in the Technology Products arena in the UK and USA. His initial venture, Speedchain, started operations in 2000 after raising start-up capital through VC funding in San Francisco and London. The company subsequently achieved a $20Million trade sale to a public (Nasdaq) US-based technology company, Vastera Inc. His second venture in 2003, Servisional, a CRM/BPM software product and consultancy company, was initially self-funded, but subsequent 3rd-party funding was achieved in 2006 through a public (FTSE) UK-based company. Eric then successfully negotiated a MBO of the company in 2008.
After re-locating to South Africa in 2009, Eric initially performed various IT consultancy assignments before joining Alacrity Technologies. He held management and executive positions within Alacrity and was asked to take on the role of CEO in 2011 after playing a pivotal role in concluding the investment deal with Capital Eye Investments, a Johannesburg based private equity technology fund.
Eric co-founded CBOS in 2014 together with Pieter Geyser and Gerhard Bouwer to deliver on their vision to enable and streamline business operations within and between their client organisations through the provision of advanced and innovative software solutions. CBOS celebrates its 10th year of operations in 2024.
Eric has a unique combination of exco and board-level CIO experience with large corporates, having been responsible for large technology teams (150+ professionals), large annual technology budgets (R500+ Million) and large project budgets (R250+ Million) and CTO / CEO experience with start-up organizations, responsible for raising start-up capital and additional funding as well as the set-up of company processes and infrastructures. He is an entrepreneur with a proven track record of successful start-ups, fund-raising and value creation.