Reshaping Culture Key to Successful Digital Transformation

As organisations rush to implement AI and automation technologies to maximise efficiency and drive competitive advantage, many overlook one of the most critical components for success: company culture. 

While the temptation of going all in on AI’s power to streamline operations has been strong – particularly amid extensive hype around the technology – realising its full potential requires an organisational culture that embraces change, experimentation and collaboration.

Too often, digital transformation initiatives stall or fail outright due to cultural resistance, lack of leadership support, siloed thinking and fear of taking risks. Companies may acquire the latest AI tools, but realising value means getting buy-in and shifting long-held mindsets across the entire workforce.

Building this starts with clear communication of the transformation strategy and how AI augments rather than replaces human capabilities. It requires investing in training to upskill employees, incentivising experimentation, and fostering an environment of continuous learning. Breaking down organisational silos allows AI’s insights to flow freely. And, perhaps most critically, leadership must role model the desired behaviours and attitudes, while empowering teams to iterate and learn from inevitable missteps along the way.

Overcoming cultural roadblocks to digital transformation

Addressing cultural barriers is crucial for successful digital transformations, particularly when implementing disruptive technologies like AI. As highlighted by Kunal Purohit, Chief Digital Services Officer at Tech Mahindra, major cultural roadblocks stem from apprehensions around emerging technologies like AI displacing workforces, but this narrative underestimates the collaborative potential of humans and technology. 

“The future of work is not man versus machine – it is man enhanced by machine. While AI will undoubtedly transform roles, it creates new opportunities for humans to focus on higher-order work involving creativity, judgement, and emotional intelligence that machines cannot yet replicate.”

To tackle this mindset, Kunal emphasises the need to upskill employees and evolve cultures to view AI as an enhancing tool rather than a threat. “Organisations must provide continuous AI training, evolving roles to leverage the human-machine partnership and instil cultures that see AI not as a threat, but as a tool to enhance human capabilities when implemented responsibly.”

According to Will Clive, Chief People Officer at Pluralsight, a “reluctance for organisations to embrace experimentation” is another major hurdle. “Successful digital transformation only happens when people step out of their comfort zones to try new technologies as a way to overcome challenges,” he says.

He advocates for cultures that “value autonomy and give employees the freedom to try new things and experiment with emerging technologies” to ensure workers understand how to effectively leverage tools like AI.

Martyn Ditchburn, EMEA CTO at Zscaler – who says that the biggest transformation roadblocks are “permission and confidence” – highlights the importance of empowering teams. “One style that works particularly well is when teams are empowered to help lead the change,” he says. “This means communicating effectively to the business as a whole to help them understand the bridge between where the business is headed and the technology needed to get there.

“This visibility gives people the confidence that these changes are going to deliver. If they are also given the permission to take time to learn the new technologies, understand how they fit into current processes, and have time to fail fast, it gives the workforce the breathing space to think ahead and embrace the new.”

The need to overcome cultural resistance

Cultural resistance and rigid mindsets pose major obstacles to capturing digital transformation’s full potential. This cultural resistance takes many forms – from fear and disengagement to confirmation bias and inertia. Overcoming this resistance demands proactively cultivating mindsets oriented towards continuous learning, human-AI collaboration and comfort with evolving processes.

Pluralsight’s Will Clive connects cultural resistance to workplace trends like “quiet quitting” and “polyworking” that reflect employee disengagement. “This can happen because organisations don’t help employees to embrace new technology, and understand how or why the business is changing and developing,” he explains. “So, the challenge for companies is to make sure employees feel valued and engaged as digital transformation projects are ongoing, especially amid a tech skills shortage where organisations need to retain talent in order to work with new technology.”

This fear of new technology presents a formidable challenge. “Organisations rooted in traditional working methods often exhibit a deep-seated resistance to change and a failure to embrace new human-machine collaborative models,” comments Tech Mahindra’s Kunal Purohit. “This mindset views AI as a threat rather than a tool to enhance human capabilities. Overcoming this requires inspirational leadership to cultivate a mindset that fosters continuous learning, empowers risk-taking, and encourages experimentation. Without an open culture celebrating human-AI symbiosis, companies will struggle to evolve roles, workflows and skillsets paired with AI’s prowess.”

Meanwhile, Zscaler’s Martyn Ditchburn cites “confirmation bias – the idea that we are always right” as a core blocker. Successful transformation requires overcoming this inertia, refactoring processes and helping people break out of the status quo.

“Digital transformations represent a significant shift to new ways of working, often organisations underestimate the effort and commitment involved and all too often under-resource the project downstream. Technical teams are often asked to deliver these projects on top of business as usual activities.”

This, he says, creates contention between the short-term and long-term requirements of the business. The result is burnout and project fatigue.

“When new technology results in a business process change, it tends to be viewed as a negative because the workforce does not want to have to re-learn what it already knows (institutional muscle memory),” he adds. “This often results in a business filled with people who look for reasons to stay the same because they are unable to see the connection between the business strategy and the technology strategy.”

Bringing employees along for the journey

When driving cultural transformation, it’s crucial for employees to be included throughout the process. “Involving employees in the change process early on, so they can provide input, feedback and feel involved with the change rather than it being done ‘to them’ is often overlooked,” Catherine Wilks, Client Partner at Slalom. “Early engagement helps address resistance, incorporates diverse perspectives and ensures alignment with the organisation’s culture and values.”

Moreover, change can be disruptive and challenging, so providing robust support mechanisms is vital. “Overlooking the need for appropriate support mechanisms can lead to burnout, low morale, and resistance,” Catherine cautions. Organisations should equip employees with resources like training, coaching, counselling and clear communication channels to build resilience and navigate changes effectively.

Equally important is establishing mechanisms for continuous feedback and improvement. “Change is rarely a linear process, and unforeseen challenges or roadblocks may arise,” she notes. “By creating channels for employees to provide feedback, share concerns, and suggest improvements, organisations can identify and address issues promptly.”

Ultimately, as Martyn concludes, success hinges on clearly articulating the vision and empowering the workforce. “If leaders are able to articulate the vision of where the business is going, employees can be brought along on that journey to help make decisions, help them communicate the barriers, and become more of a team addressing that challenge of resistance together.”

He also underscores the importance of meeting employees where they are: “The workforce wants a friction-free life. What individuals tend to miss is what is in it for them.” By involving employees in problem-solving and demonstrating how changes benefit them, leaders can cultivate a sense of ownership and willingness to collaborate on solutions. “If the workforce doesn’t understand that they have a place in solving the problems that will inevitably occur, they will bring problems and be unwilling to help find solutions.”


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