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Leading successful business transformations with Barry O’Reilly

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For companies today, transformation is not just a buzzword – it’s a business imperative. Disruptive forces like technology innovation, changing consumer preferences, and economic fluctuations mean companies must continuously evolve to stay competitive.

However, leaders face increasing demands to drive transformation with fewer resources. They must find ways to increase efficiency and profitability while also investing in growth and innovation. It’s an immense challenge.

Only 58% of technology transformation projects succeed. Change is hard in the best of times – let alone in tougher business climates. As a leader, how do you maintain urgency amid cutbacks? How do you inspire a culture shift in uncertain times?

Author and global thought leader Barry O’Reilly delivered a workshop for the CxO and executive esynergy community on Leading Business Transformation on 21st February 2024, which looked at the key components to a successful transformation.

Barry has helped business leaders go beyond theoretical concepts, offering practical insights through real-world case studies and lessons from Fortune 500 companies across various sectors with case studies from Capital One, Wells Fargo, American Airlines and Tesco Bank.

In the session, Barry shared valuable insights on how to align your strategic goals with tangible outcomes and metrics and the behaviors that are driving high performance at some of the most successful organizations today.


Leadership, culture and behavior

Many leaders prioritize changing structures and procedures during transformations. While significant, real change starts from cultural and mindset shifts throughout the organization. It’s essential to allocate time to identify desired cultural traits such as creativity, adaptability, empowerment, and alignment with the vision.

In times of transformation, leadership behaviors and culture are crucial. Leaders must authentically role model the desired changes they wish others to exhibit within the organization.

It’s essential to examine if top executives need to adapt their behaviors to align with transformation goals. Are you embracing a new mindset and modeling new approaches personally? Changing leadership habits is vital for cultural evolution.

According to business leader Christian Metzner, leaders should identify target culture changes and map specific behaviors to facilitate a swift transition. Offer coaching and training to effectively instill these new behaviors throughout the organization.

Leadership must set the tone for others to follow. Ask yourself, what behaviors will drive driving performance and what behaviors hinder it? These questions help assess limiting mindsets or behaviors that need to be “unlearned” or adjusted, like resistance to experimentation

Demonstrate the change you want to see across all levels of leadership. Address and confront limiting beliefs as they arise. Provide training and coaching to embed the new cultural DNA. This initial focus on culture and mindset establishes the groundwork for lasting transformation.

For example, Christian always left an empty chair in all his meetings for people to jump in and be the voice of a customer in sessions. He even held a raffle for someone  in the organization to do his job for a day, to see how the team responded to solving challenges without him, encouraging greater ownership and decision-making at appropriate levels.*


Roadmapping change through active stakeholder engagement and communication

Generic transformation strategies often fail when business leaders push for too much change too quickly, without securing buy-in from stakeholders or implementing changes that don’t resonate with them. The key to continual change adoption lies in tailoring transformation initiatives based on input from all stakeholders and consistently communicating progress updates.

To start, leadership must articulate a clear vision of the organization’s desired future state within two to three years, highlighting the benefits for both the organization and its stakeholders. Next, collaboratively build a transformation roadmap with incremental changes tailored towards achieving the goals that matter most to stakeholders. Seek stakeholder perspectives early and often to foster buy-in to the vision and roadmap.

During Barry’s time with the CEO of Capital One, they had three very clear objectives for their transformation;

  • Increase the percentage of customer investment with the bank
  • Increase the rate of product innovation
  • Be the place where people can do the best work of their lives

As changes are implemented, maintain regular communication to update stakeholders on progress, challenges, and achievements, ensuring continued engagement. Acknowledge and celebrate small wins and adjustments based on feedback, reassuring stakeholders that their input is valued. Establishing robust, two-way communication channels fosters transparency in decision-making and encourages stakeholders to express both support and concerns openly.

By prioritizing stakeholder buy-in and fostering transparent communication, organizations can tailor transformation initiatives and pace change according to stakeholder readiness. This thoughtful approach enhances the chances of adoption both in the short and long-term. The result is a culture and capability for continual change driven by engaged stakeholders.


Measuring success

In any large-scale organizational transformation, defining and measuring success is critical. Too often, success is viewed narrowly through a financial lens, overlooking vital aspects like customer experience and operational efficiency. The Crown Prosecution Service’s (CPS) journey to modernize its Case Management System (CMS) offers valuable insights into a more holistic approach to gauging success.

From the outset, CPS recognized the need to enhance justice through innovation. Saving time, improving intelligence, and reducing wrongful prosecutions from case errors were pivotal goals. Measuring success, therefore, had to encompass both leading and lagging factors aligned with this higher purpose.

CPS’s partnership with esynergy focused on leading indicators that could drive change towards a north star, aptly names named Polaris (North Star). Comprehensive user research and rapid prototyping helped identify recurring pain points faced by CMS users, such as inefficient manual redaction and searching processes. By closely monitoring user feedback and engagement throughout the project, CPS could make real-time adjustments to ensure the new system would meet their needs.

Simultaneously, CPS tracked lagging metrics like the reduction in case backlogs and improvement in prosecution rates. While these lagging indicators took time to materialize, they provided concrete evidence of the transformation’s impact on core operations.

Polaris is expected to save pre-charge review activity 60,953 hours per year and 51,098 hours per year for post-charge review activity. This is a total annual saving of over 112,000 hours and given the substantial user base of 3,000 daily users, the impact on prosecution rates is expected to be significant.



“It takes bold leadership and brave choices to commit to a new path. It also requires the humility to call out that what is being done today isn’t working. Teams can surprise themselves with what they can see is possible. Thinking big, starting small and learning fast what works and doesn’t has been the key to get them started—and scale from there.”

Barry O’Reilly 

Driving successful transformation in turbulent times is no easy feat, but with thoughtful leadership, an empowering culture, engaged stakeholders, and a focus on leading indicators of performance, organizations can continually evolve to thrive.

Leaders need to role model desired mindsets and behaviors that signal the cultural changes needed across the organization. When culture evolves, new ways of operating take hold.

Ultimately, whilst financial metrics are significant as retrospective indicators, the true pulse of transformational success lies in proactive measures such as employee empowerment, customer satisfaction, and the pace of innovation. These factors offer a more immediate gauge of whether endeavors will yield fruitful results. By monitoring both leading and lagging metrics, acknowledging incremental achievements, and iteratively refining strategies in response to stakeholder input, a cycle of continuous improvement is established, ready to revolutionize business.

*Click here, for more on Christian and Barry’s conversation on role modeling and culture transformation