The Reality of Digitalisation and Automation Challenges
In my advisory projects, I’ve seen first-hand how organisations struggle with digitalisation and automation. The frustration of dealing with fragmented systems, outdated processes, and internal resistance is all too common. Many businesses embark on automation journeys with the best intentions, only to find themselves stuck in misaligned efforts, budget overruns, and slow adoption. Others hesitate, unsure how to integrate new technologies with legacy infrastructure without disrupting operations.
A well-structured IT modernisation roadmap is more than just a technical guideline, it’s the foundation for sustainable growth. When executed properly, it aligns digital transformation efforts with business goals, ensures resources are allocated efficiently, and guarantees technology investments deliver real value. More importantly, it provides clarity in a world where IT modernisation often feels overwhelming.
Aligning Stakeholders and Assessing IT Systems
Before diving into solutions, it’s crucial to bring key stakeholders together through structured workshops. These sessions are not just formalities, they are the moments where leadership, IT teams, and business units align on what needs to change and why. By openly discussing challenges, expectations, and long-term goals, companies can prevent costly misunderstandings down the line.
Alongside stakeholder engagement, a deep assessment of the IT infrastructure is necessary. This includes identifying outdated systems, mapping workflows, and evaluating which tools need replacement or integration into a more modern ecosystem. Without this foundation, businesses risk implementing solutions that fail to address their core inefficiencies.
Structuring Key Workstreams and Choosing the Right Methodology
With a clear scope in place, the modernisation effort must be divided into key workstreams, ensuring manageable and strategic execution. These typically include:
- Infrastructure modernisation: Upgrading networks, enhancing security, and migrating to cloud environments.
- Process automation: Leveraging RPA (Robotic Process Automation) and AI-driven workflows to eliminate repetitive tasks.
- Application modernisation: Reworking legacy applications, integrating APIs, and enhancing system interoperability.
- Change management and training: Preparing teams for new tools and ensuring smooth adoption.
The next step is selecting the right methodology for each workstream. A Waterfall approach works well for large-scale infrastructure upgrades that require meticulous planning. Meanwhile, Agile methodologies like Scrum are better suited for software development and automation, allowing for iterative improvements and faster feedback loops. A hybrid model can offer the best of both worlds, tailoring the approach to the needs of each workstream rather than forcing a one-size-fits-all strategy.
Addressing Legacy Systems and Technical Debt
One of the biggest roadblocks to modernisation is the burden of legacy systems. These outdated platforms are often deeply embedded in operations, making a sudden transition costly and risky. Instead of rushing a complete overhaul, a phased approach allows for gradual improvements without causing disruption.
Common strategies include:
- Encapsulation: Creating APIs to extend the functionality of existing systems and enable integration with modern platforms.
- Replatforming: Migrating workloads to cloud-based infrastructure to improve scalability and cost efficiency.
- Replacement: Phasing out outdated solutions and implementing advanced, fully automated alternatives.
Creating a Realistic Timeline for IT Modernisation
To ensure momentum and prevent stagnation, a time-bound roadmap should be established. A structured timeline includes:

- Discovery & Assessment (0-3 months): Identifying inefficiencies, gathering requirements, and mapping business objectives.
- Planning & Design (3-6 months): Selecting technologies, developing integration strategies, and defining clear milestones.
- Implementation (6-12 months): Executing the plan in structured phases, incorporating Agile sprints where needed.
- Optimisation & Scaling (12+ months): Refining systems, optimising processes, and expanding automation efforts across departments.
Driving Value with Agile Sprints
Using sprints within IT modernisation allows for continuous progress instead of relying on a single large-scale rollout. Sprint planning defines deliverables, prioritises key initiatives, and ensures cross-functional collaboration. Regular retrospectives keep teams on track, allowing for iterative refinements rather than reacting to major setbacks too late in the process.
Managing Resistance to Change
Resistance to change is an inevitable challenge in IT modernisation. Employees accustomed to traditional workflows may view automation as a threat rather than an opportunity. Overcoming this requires a well-structured change management approach, including:
- Early and ongoing stakeholder engagement: Keeping leadership and teams in the loop, fostering a sense of ownership.
- Workshops and hands-on training: Educating employees on how new systems benefit them personally and professionally.
- Pilot programs and success stories: Demonstrating quick wins to build confidence and secure broader buy-in.
Final Thoughts: IT Modernisation as a Strategic Enabler
A successful IT modernisation roadmap is not just about upgrading technology; it’s about ensuring that technology serves the business, not the other way around. By combining stakeholder alignment, structured workstreams, tailored methodologies, and a phased implementation approach, organisations can achieve meaningful transformation without unnecessary risk.
With the right framework, businesses can move from frustration to innovation, embracing automation and modernisation with confidence. The key is not just in planning but in executing a roadmap that is flexible, realistic, and aligned with long-term business success.