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Digital transformation is no longer a distant ambition—it is a critical requirement for businesses striving to remain competitive and resilient. As organisations navigate an increasingly digital landscape, the shift to new technologies brings significant challenges, from overcoming resistance to change and managing budget constraints to ensuring operational stability while fostering innovation.

For many businesses, the process can be daunting. Employees may be hesitant to adopt new systems, financial limitations can hinder progress, and balancing the need for innovation with the realities of day-to-day operations often proves complex. Yet, companies that successfully embrace digital transformation find themselves better positioned to adapt to market shifts, improve efficiency, and drive long-term growth.

To better understand how organisations can tackle these challenges, we spoke with industry leaders who have successfully navigated their own digital transformation journeys. They shared insights on engaging stakeholders, fostering a culture of adaptability, and leveraging technology to create sustainable business improvements. Their experiences offer practical strategies for businesses looking to transition smoothly into the digital era—proving that while the path may be challenging, the rewards are well worth the effort.

Engaging Stakeholders and Fostering a Change-Ready Culture

One of the most significant challenges businesses face when embarking on digital transformation is resistance to change. Rich Davies, UK Managing Partner at Netcompany, says that engaging stakeholders from the outset is crucial to overcoming this hurdle. “Clear, consistent communication and strong support from the C-suite are key to empowering internal teams and driving change effectively,” he said. Davies also emphasised the dangers of budget overruns and scope creep, advising companies to establish “strong internal guardrails and maintain continuous alignment with stakeholders.”

A focus on aligning digital transformation goals with a company’s core values can also help reduce resistance, says Marcus Knight, founder of BE GREEN AI. “When the goals for digital transformation sit at the core of the organisation and its values, they take root more naturally and with much less resistance,” he explained. Knight’s approach prioritises enhancing employees’ work with digital tools rather than making their tasks more complex. He also highlighted that creating open dialogues and involving all levels of the company can make the adoption of digital tools smoother and more effective.

Chris Bird, Regional Operations Director at Ricoh Northern Europe, believes that digital transformation should be a “board-level priority” rather than a reactive measure. Drawing a parallel with team sports, Bird likened a successful transformation to a rugby team, requiring a cohesive environment where everyone maximises their unique strengths. Bird stressed the importance of authentic leadership and transparency, explaining that breaking down traditional silos and encouraging cross-functional collaboration creates a culture where innovation can thrive.

Balancing Innovation with Operational Stability

Finding the right balance between innovation and maintaining operational stability is a significant challenge for businesses.

Dean Clark, CTO at GFT, advised that building a strong digital backbone is essential to achieving this balance. “A strong digital backbone, clean and structured data, clear workflows and a well-integrated digital ecosystem are essential before integrating new digital technologies,” Clark said. He added that organisations often underestimate the cultural shift required alongside technological changes, which can lead to resistance and stalled progress.

Automation is a powerful tool in maintaining stability while adopting new technologies, according to Andre Schindler, GM EMEA and SVP Global Sales at NinjaOne. He pointed out that “automation, particularly in areas such as configurations, monitoring, endpoint management, and network operations, has the potential to improve consistency and security, reduce human error, and free up IT professionals to focus on strategic work.” Schindler’s insights highlight how automation not only boosts efficiency but also strengthens stability by providing visibility and control over all devices in a centralised manner.

Simon James, Managing Director, Data Strategy and AI at Publicis Sapient, suggested that a transparent feedback culture can help balance innovation with operational stability. “Encouraging more transparent and frequent feedback can reduce the friction between operations and innovation,” he said, advocating for an approach that prioritises agility and responsiveness to changing business needs. James also emphasised the importance of aligning technology initiatives with existing business priorities to ensure they serve as strategic enablers rather than standalone projects.

Measuring Success and Learning from Failures

Measuring the success of digital transformation initiatives and learning from failures is a critical part of the process. Sean Bailey, Head of Intelligent Automation at Ten10, shared a cautionary tale of over-ambition leading to setbacks in a project. “The takeaway? Start small, understand your data’s messy realities, and set realistic expectations,” he said, stressing that manageable projects are often the best starting point to build trust and achieve tangible wins. Bailey also suggested using pilot projects to test new technologies on a small scale before wider adoption.

Mark Wilkinson, SVP for the Global Business Network at OpenText, underscored the importance of a strong data foundation to avoid digital friction. He explained that “a strong data foundation is key for empowering new solutions and getting the full benefit from them, such as producing a significant return on investment.” Wilkinson noted that many digital transformation initiatives fail because they overlook the need for clean, structured data and strong governance practices.

Turning Challenges into Opportunities

The insights from these industry leaders reveal that successful digital transformation is not solely about technology—it’s about people, culture, and strategic alignment. By engaging stakeholders, maintaining a balance between innovation and stability, and learning from both successes and failures, businesses can turn digital transformation challenges into opportunities for sustainable growth.

As digital transformation continues to evolve, organisations that approach change with a clear vision, strong leadership, and an adaptable culture will be best positioned to thrive in an increasingly digital world. These companies will not only leverage technology to improve processes but also build a culture that supports continuous innovation and operational excellence.

James Haworth, Head of Technology, A&O IT Group.

What are the most common obstacles organisations face when embarking on a digital transformation journey, and how can they be mitigated?

“Organisations frequently encounter challenges such as outdated legacy systems, skills shortages, cybersecurity concerns, and resistance to change. In our experience, the lack of a shared vision and clear strategy can be particularly detrimental.

“We believe digital transformation isn’t just about technology – it’s about people. It requires engaging voices across the entire organisation, from the front line to the boardroom, to foster an environment of collective ownership. Our approach emphasises developing a tailored roadmap that not only aligns with business objectives but also nurtures a culture of continuous learning and collaboration.

“By running agile pilot projects and encouraging open dialogue, organisations can demystify new technologies and empower every team member to contribute to the transformation. This inclusive process turns obstacles into opportunities and creates a foundation where innovative ideas, drawn from diverse perspectives, become the engine for sustainable change.”

How can businesses successfully implement AI and automation without disrupting existing workflows or overwhelming employees?

“Successfully integrating AI and automation is about harmonising technology with the human experience. We’ve found that a measured, iterative approach works best – one that respects existing workflows while gradually introducing AI as a natural extension of people’s work. Instead of a top-down mandate, we advocate for involving teams early on to explore where AI can ease repetitive tasks and enhance creativity.

“By starting with targeted pilot projects, organisations can adapt and learn in a controlled environment, ensuring that every stakeholder feels supported and valued. Training and open communication are vital to emphasise that AI is here to augment human capability, not replace it. This approach not only minimises disruptions but also cultivates a sense of ownership and curiosity among employees, empowering them to shape a future where technology works in tandem with diverse talents and experiences.”

Beyond AI, what other emerging technologies (such as blockchain, IoT, or quantum computing) should businesses be paying attention to, and why?

“While AI remains a transformative force, we see a wealth of opportunity in other emerging technologies that often go overlooked. Technologies like IoT, blockchain, and quantum computing are redefining how we capture, secure, and process information. IoT, for example, connects our physical and digital worlds, creating rich, real-time insights that can revolutionise decision-making.

“Blockchain offers the promise of trust and transparency in systems that demand secure, verifiable data flows, while quantum computing is beginning to tackle problems that were once thought unsolvable.

“We view technology as inherently personal, and integrating these tools means considering the human element at every step. It’s about ensuring that as we adopt new capabilities, we remain inclusive – leveraging diverse perspectives to assess the relevance and impact of each technology. This holistic approach not only spurs innovation but also ensures that transformation is grounded in practicality and shared human values.”

What role does company culture play in the success of digital transformation initiatives, and how can leaders foster an innovation-driven mindset?

“Company culture is the beating heart of digital transformation. In our view, transformation isn’t solely about technology – it’s about nurturing an environment where every voice matters. Leaders who succeed in digital transformation understand that encouraging diversity of thought, experience, and capability is essential.

“We advocate for creating spaces where collaboration and experimentation are not only welcomed but celebrated. This might include cross-functional workshops, innovation labs, or even informal forums that allow ideas to flourish outside traditional hierarchies.

“By integrating continuous learning and open dialogue into the everyday fabric of an organisation, leaders can help build a culture that is resilient and agile. When technology is perceived as a personal tool that empowers every team member, the entire organisation benefits. Embracing this mindset shifts the focus from simply managing change to inspiring innovation, paving the way for transformation that is as inclusive as it is impactful.”

What strategies have you found most effective in securing executive buy-in and stakeholder engagement for AI and other digital transformation projects?

“Achieving broad-based support for digital transformation is about creating a compelling narrative that resonates on all levels – not just with executives but with every stakeholder. We find that a strong business case that connects strategic goals with tangible benefits can open the door, but it’s the inclusion of diverse perspectives that truly drives engagement.

“We work with clients to craft proposals that demonstrate how digital initiatives can solve real-world problems while enhancing creativity and productivity across the organisation. Involving voices from every corner – from operational teams to customer-facing roles – ensures that the vision is inclusive and well rounded.

“Regular, transparent communication and small, impactful wins help build momentum, making the transformation process a collaborative endeavour rather than a top-down directive. This approach underscores that digital transformation is not just an executive priority – it’s a collective endeavour that thrives on the unique insights and contributions of all employees.”

How can organisations strike the right balance between innovation and operational stability when adopting new digital technologies?

“Striking a balance between innovation and stability is a dynamic challenge that requires both strategic foresight and operational discipline. We encourage organisations to adopt a dual operating model that creates a safe space for experimentation while safeguarding essential processes. Innovation “sandboxes” allow teams to trial new ideas without jeopardising core operations, enabling controlled risk-taking and rapid learning.

“By maintaining robust legacy systems alongside these exploratory initiatives, organisations can ensure continuity while embracing change. We also believe that tracking clear, distinct metrics for innovation and operational performance is crucial.

“This dual focus allows businesses to celebrate breakthroughs without compromising the reliability that their customers and employees depend on. Ultimately, by weaving innovation into the everyday fabric of operations and valuing input from all levels of the organisation, businesses can achieve a harmonious balance that drives both progress and stability.”

What are some key lessons from failed digital transformation initiatives – particularly those involving AI and data-driven technologies – and how can businesses avoid similar mistakes?

“Learning from failure is a critical part of any digital transformation journey. One key lesson we’ve observed is that neglecting the human element – such as change management and data quality – often leads to setbacks. Too often, projects stumble when technology is introduced without adequately preparing teams for the shift, or when poor data quality undermines the value of AI initiatives. We advocate for setting clear, measurable objectives and establishing robust data governance from the start.

“Moreover, embracing small-scale experiments can uncover insights and foster learning without overwhelming the organisation. The real takeaway is that digital transformation must be managed holistically, blending technology with thoughtful change management and an inclusive approach that values diverse perspectives. By encouraging open feedback and learning from early missteps, organisations can build resilience and avoid repeating common mistakes, setting a course for sustained and meaningful progress.”

How do you measure the success of digital transformation initiatives, including AI adoption, and what metrics should organisations prioritise?

“Measuring success in digital transformation is about capturing both quantitative improvements and qualitative impacts. We look beyond traditional metrics to assess how technology enhances efficiency – often noting improvements in the range of 15–20% – while also monitoring operational cost reductions and customer satisfaction levels.

“Equally important are the cultural and behavioural shifts within the organisation: metrics like employee engagement, training completion, and collaborative innovation provide a fuller picture of transformation success. Establishing a baseline before implementation and setting clear, incremental targets helps track progress over time.

“This balanced approach ensures that transformation isn’t judged solely on immediate ROI but on its ability to foster a more agile, resilient, and inclusive organisation. Ultimately, the true measure of success is not just how technology performs, but how it empowers people and creates a more dynamic, forward-thinking culture.

“Digital transformation is a journey that goes far beyond the adoption of new technologies – it’s about reimagining how we work and live together. We see technology as deeply personal, an enabler that should empower every individual in an organisation, regardless of their role. Our philosophy is that innovation thrives when diverse voices come together to challenge the status quo and envision new possibilities.

“By embracing a culture of inclusivity and continuous learning, organisations can transform challenges into opportunities for growth. We encourage leaders to view transformation not as a series of projects but as an ongoing evolution – one that values every perspective and leverages the unique talents of all team members. In a world of constant change, it’s this commitment to human-centred innovation that truly sets apart the leaders of tomorrow.”