top of page

Navigating the First 100 Days as a CIO: Richard Keenlyside

Updated: Feb 7

An image of RJK with the words CIO
Richard Keenlyside / CIO


The role of a Chief Information Officer (CIO) is one of the most challenging and rewarding positions in the business world. The first 100 days are critical and can set the tone for the rest of the tenure. Richard Keenlyside, an accomplished CIO and transformation director, provides invaluable insights on navigating this crucial period.

Setting the Stage: Understanding the Role of a CIO

A CIO's role is no longer confined to managing IT infrastructure. Today, CIOs are strategic partners who align technology initiatives with business goals. Richard Keenlyside, with his extensive experience in various sectors like retail, manufacturing, logistics, facilities management, transport, and financial services, has demonstrated this strategic mindset throughout his career.

The First 100 Days: A Strategic Approach

Building Relationships

One of the first tasks a CIO should undertake is to establish excellent communication and stakeholder management skills. This involves developing a thorough understanding of the organization's business model, strategic goals, and key stakeholders. The CIO should actively engage with these stakeholders to understand their needs, expectations, and concerns. This can be achieved through regular meetings, surveys, and other forms of feedback.

The CIO should also focus on building a high-performing IT team. This includes hiring the right people, providing them with the necessary training and resources, and fostering a culture of innovation and continuous improvement. The CIO should also establish clear roles and responsibilities within the team to ensure efficient and effective operations.

Strategic IT Roadmap

Another crucial task for the CIO is to create a strategic IT roadmap. This roadmap should align with the company's overall strategy and provide a clear path for the implementation of technology initiatives. It should include timelines, budgets, and key milestones, and should be regularly updated to reflect changes in the business environment or strategic direction.

Robust IT Governance & Risk Management Practices

The CIO should implement robust IT governance and risk management practices. This includes establishing policies and procedures for IT decision-making, ensuring compliance with relevant laws and regulations, and managing IT risks.

Understanding the Business Landscape

A comprehensive understanding of the business landscape is crucial. Keenlyside, in his role as IT Director for J Sainsbury's PLC, managed specialist areas such as Finance (CODA)-Oracle, HR & Payroll Systems, E-commerce/Internet Systems, Data warehousing, Supply Chain Logistics, and Store Point-of-Sale Systems. This broad understanding allowed him to align IT initiatives with business goals effectively.

Implementing Technology Initiatives

The first 100 days are also an opportunity to introduce new technology initiatives. Keenlyside, for instance, introduced PowerBI reporting and dashboards to provide further real-time analysis, improving accuracy and efficiency in his roles.

Building out and aligning the IT strategy

The first 100 days present an opportunity to define an IT strategy that aligns with business growth and stability, ensuring that IT remains fit for purpose to support the business. During this crucial period, it is vital to identify key technological needs and opportunities that can drive the company forward. This involves understanding the business objectives and translating them into a comprehensive IT roadmap.

The strategy should focus on improving operational efficiency, enhancing customer experience, and fostering innovation. It should also address potential risks and challenges, including cybersecurity threats and system downtime. The strategy should be flexible enough to adapt to changing business requirements and technological advancements.

In addition, it is important to establish strong communication channels between the IT department and other business units. This will facilitate better understanding and cooperation, leading to more effective implementation of IT initiatives.

Moreover, the strategy should include a well-defined IT governance framework to ensure compliance with regulatory requirements and industry standards. It should also incorporate a robust IT infrastructure plan that supports the scalability and resilience of business operations.

Furthermore, the strategy should prioritise investments in technologies that deliver the highest value to the business. This may include areas such as cloud computing, data analytics, artificial intelligence, and digital transformation.

By taking these steps, the IT strategy can become a powerful tool for driving business growth and stability, positioning the company for long-term success in the digital age.

The Path Forward: Beyond the First 100 Days

After the initial 100 days, the CIO's role evolves to maintain the momentum gained. Keenlyside's career demonstrates this evolution. For instance, he delivered a five-year strategic roadmap and executed a business-focused IT strategy for cloud-based, cloud-first, and agile, working with SaaS, IaaS, mobile, and BYOD.


The first 100 days as a CIO are pivotal. They set the stage for the CIO's tenure and can significantly impact the business's trajectory. Richard Keenlyside's experience provides valuable insights into navigating this crucial period and beyond, demonstrating the importance of strategic thinking, relationship building, and technology implementation.

Unlock the Secrets to Successful CIO Leadership and Strategic Planning with Richard Keenlyside - a seasoned expert in the field. Based in Yarm, North Yorkshire, Richard leverages more than three decades of experience to guide you through the challenges of transitioning to a CIO role. Discover the best practices for CIO management, onboarding, and strategic planning. Navigate your first 100 days as a CIO with confidence and expertise.

7 views0 comments


Rated 0 out of 5 stars.
No ratings yet

Add a rating
bottom of page