Five years ago, the business world was abuzz with talk of digital transformation, cloud computing, and the "Agile revolution." Fast forward to 2025, and while these concepts still dominate, the expectations around technology leadership and followership have evolved dramatically. The question is no longer whether technology plays a role in business operations, but how leaders can harness it as a competitive edge.
Reflecting on the insights shared in my 2020 podcast, and comparing them to the realities of 2025, it becomes clear that the rules of being a leader or follower in technology have both endured and transformed. Below, we unpack what’s still relevant, what’s evolved, and how organisations can lead in this new landscape.
The Enduring Truths from 2020
- Technology as a Value Driver
One insight that remains steadfast is the understanding that technology drives opportunities. As noted in 2020, organisations that realised the potential of technology to create new products, enter new markets, and scale globally are often the ones that thrive. Fast forward to 2025, this principle is as relevant as ever. However, the speed and complexity at which technology enables these opportunities have accelerated beyond what was then imagined.
For leaders today, the challenge isn’t understanding whether technology adds value, but recognising how quickly it can, and ensuring their teams can keep pace. Organisations still resting on incremental progress risk losing to those with an innovation-first mindset.
- Trust as a Leadership Cornerstone
The trust equation shared in our 2020 discussion remains highly relevant today. Credibility, reliability, intimacy, and self-orientation are still key pillars for leadership, particularly in technology roles. However, in 2025, stakeholders demand not only trust from their technology teams but transparency as well.
Executives must not only deliver outcomes but bring clarity to processes, enabling peers and teams to witness the value of technology in real-time. Trust today goes beyond avoiding failure; it’s about shaping a culture of openness where wins and lessons alike are shared regularly across the organisation.
- Technology Needs Leadership at the Table
The need for CIOs and other tech leaders to have a "seat at the table” is as strong as it was five years ago. Organisations today are far more likely to view technology departments as strategic partners, moving away from the outdated perception of IT being mere order-takers.
That said, some organisations still struggle with embedding technology fully into executive decision-making. Leaders must continue to advocate for a "tech-first" mindset—not as separate from the business, but as an integral part of every strategy discussion.
What’s Changed in 2025?
While the core tenets remain, the technological and business landscape has shifted in the last five years.
AI and Data-Driven Decision Making Are Now Table Stakes
Back in 2020, organisations were still grappling with how to extract value from unstructured data and AI. Today, machine learning and AI are no longer optional "nice-to-have" tools; they are essential. Companies that excel in 2025 leverage predictive analytics, natural language processing, and advanced AI to automate decision-making and identify opportunities within vast troves of data. For example, emerging AI tools now analyse not just operational data but also unstructured data like email patterns to improve team effectiveness.
The Decentralisation of Technology Teams
Paul predicted a future where IT isn’t a separate department but is embedded across the organisation. By 2025, this prediction has largely come to fruition. Technology is now "just a thing businesses do." Developers often sit within specific departments rather than under a central IT umbrella, working closely with business teams to achieve shared goals.
Shadow IT is Just IT
The controversial debate around shadow IT has evolved significantly. By 2025, the spotlight is shifting away from the tools brought in by business units without IT oversight and towards managing "shadow data" risks. The key message today is that what used to be labelled shadow IT is simply an extension of business innovation. High-performing businesses don’t fight it; instead, they put frameworks in place to ensure these tools integrate securely and efficiently into the larger ecosystem..
Technology Leadership Is Now Multifaceted
The role of the CIO has evolved. To lead effectively, CIOs must be both visionaries and orchestrators of chaos. They no longer need to master all 112 technical skills outlined in frameworks like SFIA, but they must surround themselves with specialists and foster the right behaviours across their teams. Collaborative leadership has replaced the "heroic IT leader" model, with boards increasingly recognising that leadership is a team effort.
Agility Extended Beyond Tech
Agility is now a company-wide philosophy, no longer limited to IT. Legal, finance, and risk teams have adapted to support iterative methods of working. For example, rather than insisting on rigid, upfront project budgets, finance teams now apply more dynamic approaches to funding innovation.
Navigating New Barriers
Despite these advancements, many organisations still face hurdles when it comes to leading with technology.
- Tech-Team Integration: Technology teams often struggle to integrate fully with business teams. Jargon remains a barrier, and many CEOs still view IT as "the wizards in the corner." Visualising workflows through tools like Kanban boards has helped, but empathy and understanding between business and tech teams must continue to evolve.
- Data Consistency: While decentralisation is helpful, maintaining a single source of truth for business-critical data is more challenging than ever. Shadow data (multiple, inconsistent copies of the same information) is an increasing risk.
- Skills Gaps: Rapid innovation has created gaps in critical technical skills. Organisations must be transparent about what they don’t know and lean on strong vendor partnerships to fill capability gaps.
- Sustainability & Ethical AI Concerns: Businesses are under increasing pressure to operate sustainably in how they use technology. Ethical use of machine learning and AI to minimise bias and environmental impact is now a prominent consideration for any forward-thinking organisation.
What Businesses Can Do to Lead, Not Follow
To be technology leaders in 2025, organisations need to adopt a proactive and forward-thinking mindset. Here are some strategies to help your business stay ahead of the curve:
Be Culture Architects
Invest time in building stronger relationships between technology and business teams. Use the trust equation Paul Littlefair highlighted in 2020: credibility, reliability, and intimacy combined with selflessness. Trust is the foundation for collaboration and innovation.
Orchestrate the Chaos
Empower all departments to play a role in technology decisions. Equip them with the frameworks they need to do so securely and responsibly.
Leverage Emerging Technologies Thoughtfully
Don’t chase "shiny new toys." Instead, identify emerging tech (like AI) that solves specific business challenges, and ensure its implementation aligns with your strategic goals.
Address Skills Gaps with a Blended Approach
Upskill internal teams while also partnering with external vendors to bring in expertise. By balancing long-term capability building with quick wins, you can achieve sustainable technology growth.
Actively Influence Agile Across the Business
Encourage agility not just within IT but across all business functions. Work proactively with legal, finance, and HR teams to help them adapt to iterative processes. Agile isn’t just a methodology; it’s a cultural mindset that drives resilience in a fast-paced world.
The Time to Lead With Technology is Now
By 2025, one thing is clear: technology leadership means more than just adopting tools or "going digital." It’s about embedding technology into the fabric of your organisation, fostering a culture of trust and collaboration, and continuously learning and adapting to new challenges.
Are you ready to take your organisation from follower to leader? Start by assessing your approach to technology and business agility.
