By Anna Ladipo
July 9, 2026
There is a particular kind of organizational ambition that sounds straightforward on paper but turns out to be anything but. The decision to transition an IT organization from waterfall to agile methodology is one of them. It is not a process change. It is a mindset shift. And mindset shifts do not happen by mandate.
I was part of one of these Agile transformations in the mid-2010s at a major Canadian financial institution. I was asked to organize a Project Management (PM) Day, bringing together project management teams from Toronto, Waterloo, Montreal, and India to mark the beginning of a journey toward 100% agile adoption, including the rollout of a new enterprise tool.
I was at the inception of that Agile initiative and remained closely aware of its progress after moving on. It succeeded not because someone flipped a switch, but because conditions the right conditions for change were intentionally created.
The data supports what I observed firsthand. According to the Standish Group Chaos Report, agile projects have a success rate more than three times higher than waterfall projects in IT environments. Yet research also shows that most agile transformations still struggle or fail outright, not because of the methodology itself, but because of how the change is managed.
Here is what I learned from that transformation, and from the organizations I have consulted with since.
1) Change starts at the top. Every time.
This is the single most consistent finding across agile transformations that fail. Leadership endorses the initiative in a kickoff meeting and then returns to managing the way they always have. Teams are expected to change. Executives are not. The result is predictable.
A McKinsey analysis found that 70% of agile transformations fail due to cultural resistance rather than methodology flaws. PMI research identified leadership behavior change as the number one predictor of agile success.
At the PM Day I organized, the keynote was delivered by Marnie McBean, a three-time Olympic gold medalist. She spoke about the mindset required to perform under pressure, to adapt, and to commit to a new way. One line stayed with me: you do not expect change, you anticipate it. That framing set the tone for everything that followed. Leadership must be in that room, not just in name, but in posture.
Best practice: Transformation must be led from the executive level, visibly and consistently. If leaders are not changing how they work, no amount of training or tooling will move the organization.
2) Create the conditions before you launch the initiative.
The PM Day was more than a kickoff event. It was a deliberate effort to create shared experience before the hard work began. Teams from multiple cities came together to connect, learn, and align around a common vision. That shared sense of purpose-built momentum and laid the foundation for the change that followed.
People are resistant to change even when the current way of working is not efficient. That resistance is not irrational. It is human. Change carries risk: the risk of looking incompetent during the learning curve, the risk of losing influence, the risk of a new system that does not work the way the old one did. Acknowledging that reality and building community around the shared journey is not a soft activity. It is strategic.
The vision for the transformation needs to be shared everywhere, cascaded by every level of management, and visible throughout the organization.
Best practice: Invest in the launch. Bring people together. Make the shared vision tangible before you ask anyone to change how they work.
3) Use pilots, waves, and evangelists.
One of the most effective things you can do in a large-scale transformation is resist the urge to roll everything out at once. A phased approach protects the workforce from being overwhelmed, generates early evidence of success, and allows you to refine the approach before it reaches the full organization.
Start with a pilot. Identify your strongest people, those who are credible, adaptable, and respected by their peers, and have them lead the first wave. Their success becomes the proof of concept. Their experience becomes the training ground for what comes next.
Best practice: Run a structured pilot with a defined cohort. Roll out in waves. Assign change evangelists at every level of the organization.
4) Define your metrics before you launch, not after.
Define your Key Performance Indicators (KPIs) before the transformation begins. What does 100% adoption mean? How will you measure it? What delivery metrics will you track? What does a successful sprint look like compared to a successful waterfall phase? How will you know when the tool has been adopted, not just installed?
Those metrics need to be shared, tracked visibly, and celebrated when milestones are reached. A celebratory environment is genuinely motivating. Recognition of progress, however incremental, reinforces that the effort is working and that people’s contributions are seen.
Best practice: Define your success metrics at the outset. Track them transparently. Celebrate milestones publicly and consistently.
5) Anticipate resistance, build support, and keep listening.
No transformation goes exactly as planned. Resistance will surface. Some of it will come from the teams doing the work. Some of it, most of it, will come from middle management.
Build formal support structures. Create channels where people can ask questions, flag issues, and propose improvements without fear. Make it clear that the transformation is not expected to be perfect on the first pass. Build in the assumption that there will be tweaks and create a process for receiving and acting on that feedback.
Continuous improvement is not a closing phase. It is an ongoing posture. Open pipelines for people using the new methodology to propose improvements, have forums to hear their voices, and respond visibly when ideas are acted on.
Best practice: Anticipate resistance at every level. Build formal support structures. Create a feedback loop and use it.
Your Transformation Checklist: 5 Principles for Leading Change
Whether you are leading a methodology shift, a technology rollout, or any large-scale organizational change, use this as your guide:
| Change Principle | Apply It Today | |
|---|---|---|
| ☐ | Lead from the top | Secure genuine executive buy-in. Leaders must change how they work, not just endorse the initiative. |
| ☐ | Build the conditions | Invest in a launch that creates shared experience and visible commitment before the hard work begins. |
| ☐ | Pilot, then wave | Start with your strongest people. Roll out in structured waves. Assign change evangelists throughout. |
| ☐ | Define metrics early | Set your KPIs before launch. Track progress transparently. Celebrate milestones publicly. |
| ☐ | Listen and improve | Build formal support structures. Create feedback loops. Plan for iteration, not perfection. |
A Final Reflection
The transformation I was part of at that financial institution succeeded. Not because the methodology was right, though it was. Not because technology was well chosen, though it was. It succeeded because the people who led it understood that change is a human process before it is a technical one.
Marnie McBean was right. You do not expect change. You anticipate it. You prepare for it. You create the conditions for it. You commit to it at every level of the organization, from the executive suite to the newest team member.
The organizations that get this right do not just adopt agile. They become more adaptive. In a landscape that keeps shifting, that capacity is one of the most valuable things a team can build.
Anna Ladipo is an Associate Professor and Academic Director of a Project Management Certificate Program at a leading research university in Texas where I teach graduate-level courses in project management, operations management, and leadership.
With over 20 years of experience leading enterprise transformation programs at Fortune 500 companies across banking, insurance, and financial services, I bring real-world executive expertise into the classroom and beyond. My work sits at the intersection of industry, academia, entrepreneurship, and professional development equipping leaders at every stage with the tools to deliver results.
As the founder of NGSIT Inc. and its subsidiary Luxstopp, I have delivered project management and leadership training to corporate clients across North America while supporting entrepreneurs and small business owners in building and scaling their online presence.
