A reflection on leadership, transformation, and the quiet victories that matter.
Large transformation programmes rarely unfold in straight lines. The opening stages often look deceptively clear, but very quickly the entire initiative begins to resemble the London Tube map — intricate, layered, and full of intersections and interdependencies that all have to work in harmony.
I recently rolled off a multi-year digital transformation programme for a major enterprise. It spanned multiple work streams, involved reshaping critical business processes, and required a rethink of how an organisation operated at its core. While the journey didn’t end with the traditional chequered-flag finish, I walked away feeling that it was one of the most successful experiences of my career.
This is a reflection on that journey, purposefully high-level and anonymised, focusing on the lessons, the people issues, and the quiet wins that matter.
The Ambition and the Reality
The programme was a large-scale digital transformation centred on modernising a critical revenue-generating function. It involved multiple parallel work streams, a phased release roadmap, and deep re-architecture of business processes that had been run on legacy applications for years.
I led one of the feature teams — a dedicated work stream with considerable business and technical complexity. We were tasked with designing and building modernised processes on our platform, while guiding stakeholders through what the future could and should look like. This meant translating years of manual ways of working into an automated, structured and scalable system.
The environment was fast-moving, layered, and required clarity, leadership and strong design principles to keep things on track.
The Challenges We Navigated
Programmes of this scale always attract a wide spectrum of challenges, and this one was no exception.
- Technical complexity showed up in the integration of multiple systems, solution patterns and architectural constraints that needed to align seamlessly.
- Functional complexity came from reimagining legacy business processes for a modern platform — often requiring education, reframing and patience as stakeholders understood the art of the possible.
- Inter-personal relationship dynamics emerged naturally across a broad ecosystem of senior architects, delivery leads and managers, each with their own approaches and expectations. Political currents existed, as they do in any programme of this scale. Alignment required maturity, communication and the willingness to bridge perspectives.
- Resourcing challenges added another layer — rapid ramp-ups, imperfect skill matches, working across timezones in high-pressure delivery targets. And the odd curve-balls thrown like and an urgent need to stabilise a new team quickly.
- And finally, multiple moving parts and the pace. Our team was simultaneously delivering across four release tracks — requirements, design, development and testing — each with its own pressures and interdependencies.
This complexity was real, and it tested every dimension of leadership and delivery. And now, after it is all over, I feel these most intense parts were the most satisfying and fun!
What Made Our Team Stand Out
Despite the challenges, my team emerged as one of the steadying forces in the programme — a reliable, high-performing group whose work consistently earned trust and recognition. Looking back, three principles shaped this outcome:
- Servant Leadership and Empowerment
- Rigorous Design Discipline
- A Culture of Collaboration and Alignment
My leadership style is grounded in enabling others to succeed and lead. I set direction, structure and guardrails, but gave individuals room to decide, experiment and take ownership. This created a culture where people felt accountable, confident and trusted — not managed. We placed motivated, thoughtful individuals in key functional and technical areas and empowered them to steer their domains. This decentralised strength became one of our biggest assets.
A whole lot of credit is also due to my counterparts in the customer leadership for such empowerment across our team. They provided a psychological safety net for individuals to shed the fear of failure and excel in their roles and responsibilities.
One of our proudest achievements was the strength of our design work. We created a thoughtful, well-structured blueprint for a highly complex landscape — breaking it down into digestible phases and ensuring every detail had been considered before external reviews. This rigour became the backbone of our credibility. It made conversations easier, decisions clearer, and stakeholders more confident in our direction. There is no shortcut to success and we took pride in our design due-diligence and feedback mechanisms.
We worked with the customer team as one integrated unit. Barriers dissolved early. There was clarity in communication, honesty in difficult moments, and a shared commitment to quality. Our interpersonal relationships — the trust, the respect, the willingness to listen — elevated our work far beyond the mechanics of delivery.
These three principles were the foundation of our success.
A Softer Lesson: Leadership Shapes Outcomes More Than Plans Do
One of the key reflections for me was observing how shifts in organisational leadership can influence the direction of a large-scale transformation. When new leadership brings different priorities or perspectives, alignment becomes harder and the programme’s trajectory can change rapidly.
This experience reinforced a subtle truth: even the most well-run delivery teams require consistent sponsorship and clarity of vision at the top. When that alignment is disrupted, the programme’s momentum inevitably shifts.
The lesson wasn’t harsh — just human. Organisations evolve, priorities shift, people change roles. Transformation needs steady leadership as much as it needs strong execution.
Personal Takeaways
This journey has shaped my thinking and reinforced my confidence in several meaningful ways. These are the takeaways I carry with me:
- Relationships matter - Building meaningful connections and caring about people — genuinely — creates trust and resilience in high-pressure environments.
- No shortcuts to success - You will have to dig-deep and bring out your expertise in Salesforce design and large-scale transformation architecture; it’s one of the cornerstones of credible leadership. It builds trust and confidence among stakeholders.
- Trust your methods - With years of experience, all of us develop our own methods of doing things correctly, we must rely on frameworks and ways of working that consistently bring clarity, quality and alignment. For me, breaking down large problems into smaller ones, streamlining and prioritising worked really well.
- Confidence in your abilities - One should place confidence in their leadership, their judgement, and their ability to navigate complexity and ambiguity. Even if it doesn’t show in the short term, it will reflect in the long term success.
- Have fun and stay light - These programmes can be intense; the ability to laugh, lighten the room, and see the humour in difficult moments keeps teams grounded and human. If you have to do it over many years, it has to be fun!
