DevOps practices and Agile methodologies are widely regarded as faster, more responsive alternatives to the traditional linear Waterfall model of software development. But adopting them successfully demands more than a process change — it requires a genuine cultural shift across teams, leadership, and even supplier relationships. Four experienced IT leaders shared how they are making that shift a competitive advantage. (Original reporting: ZDNet.)
1. Find the Projects That Actually Need a Flexible Approach
Gideon Kay, European CIO at media and digital marketing firm Dentsu Aegis Network, describes rapid adoption of DevOps driven by a heavy move to cloud infrastructure and data platforms. The pace of change in media and advertising made long Waterfall cycles impractical: disappearing into a six-to-nine-month development huddle would mean the market had moved on before the project shipped.
Critically, Kay resists the temptation to label every project Agile by default. His team still runs Waterfall projects where the requirements are well understood and unlikely to shift. The principle is to choose the right methodology for the context, not to be dogmatic.
“We’ve not come in with the stance that we’re only using Agile. We’re very open and able to run waterfall projects — and I insist that we can run waterfall projects if it’s the right thing to do. What we don’t want to do is simply badge every project as Agile and get on with development.”
Gideon Kay, European CIO, Dentsu Aegis Network
For data-intensive, platform-driven industries like media, Kay argues that regular two-week sprint cadences build organisational confidence and capability over time — but only when the methodology is applied where it genuinely fits.
2. Focus on Honing Your Leadership Technique
Phil Lewis, Director of Digital Experience at clothing retailer Boden, sees DevOps as inseparable from Agile delivery. For Boden, which was undergoing a broader digital transformation including a shift to cloud-hosted business applications, running Agile without DevOps tooling and culture was not a viable option.
“You can’t do Agile without DevOps. We’re working on both in parallel right now. If you want to move quickly with advanced technology, DevOps is critical.”
Phil Lewis, Director of Digital Experience, Boden
Lewis acknowledges a practical constraint: DevOps is a niche skill set and the talent market is competitive. New hires typically work across IT, digital, and marketing functions — underlining that DevOps is inherently cross-functional rather than siloed within engineering.
His most important lesson, however, is about leadership behaviour. Moving to an Agile and DevOps model means leaders must change how they interact with their teams. The leader’s primary job becomes creating psychological safety and removing blockers — not directing every task.
“The biggest learning for me is that the way you interact with your team needs to change. Your job really is to create a safe environment and protect the team.”
Phil Lewis, Boden
3. Set Clear Boundaries to Empower People
Tarah Lourens, then Group CTO at financial services company Wonga, highlights a counterintuitive truth about Agile adoption: freedom without structure does not produce empowerment — it produces anxiety. In a tightly regulated environment, employees often assume more constraints exist than actually do, making them reluctant to take initiative.
“It’s difficult to make people feel empowered — one of our biggest challenges is that people believe blocks exist, when they actually do not.”
Tarah Lourens, Group CTO, Wonga
Lourens’ solution is to be explicit about accountability and constraints. Once people understand exactly what they are responsible for and the boundaries within which they operate, ambiguity dissolves and genuine autonomy becomes possible.
“Ambiguity makes people uncertain. Once people understand the constraints they’re working within, they feel very empowered. Empowerment doesn’t work without boundaries.”
Tarah Lourens, Wonga
This is a useful corrective to simplistic readings of Agile as purely free-form or unstructured. Effective Agile delivery depends on clear roles, explicit acceptance criteria, and well-understood team agreements — the flexibility is in how the work gets done, not in whether expectations exist.
4. Work With Vendors to Build Flexibility Into Contracts and Projects
Martyn Wallace, Chief Digital Officer for the Scottish Local Government Digital Office, faces a challenge common to public sector organisations: procurement and contract structures designed for Waterfall projects actively undermine Agile delivery.
Traditional public sector IT procurement starts with an exhaustive functional specification, locks in a multi-year contract, and then charges heavily for any change requests. By the time the project completes, policies and business processes may have changed so significantly that the delivered system is already outdated.
“Our work is not about the traditional method of going out with a long functional specification list as long as your arm. It’s recognising what outcomes you want to achieve and going back to the IT industry to hear their way of meeting those objectives.”
Martyn Wallace, Chief Digital Officer, Scottish Local Government Digital Office
Wallace’s approach reframes the conversation from prescribed features to desired outcomes, then invites suppliers to propose how those outcomes can be met iteratively. This requires councils to trust vendors as collaborative partners rather than managing them through contract compliance — a significant cultural shift for organisations accustomed to detailed specifications and change-control procedures.
Key Takeaways for IT Leaders
- Be selective, not dogmatic. Not every project benefits from Agile. Assess requirements stability and rate of change before choosing a methodology.
- Agile and DevOps are interdependent. Attempting Agile delivery without the CI/CD pipelines, automation, and cross-functional culture of DevOps creates bottlenecks that undermine sprint cadence.
- Leadership behaviour must change first. Moving to Agile while retaining command-and-control management sends contradictory signals. Leaders need to shift toward coaching, removing obstacles, and creating safety.
- Empowerment requires clear constraints. Define accountability explicitly. Ambiguity does not create freedom — it creates paralysis.
- Procurement and vendor relationships need to evolve. Outcome-based contracting and collaborative supplier engagement are prerequisites for Agile delivery in organisations that rely on third-party technology providers.
The common thread across all four leaders is that Agile and DevOps transformations succeed or fail at the cultural layer, not the tooling layer. Technology enables the change; leadership, trust, and clear expectations sustain it.