On May 19th 2026 we brought together a group of senior transformation leaders from across banking, payments and financial services for a closed breakfast roundtable at Duck & Waffle.  

Facilitated by Mark Davidson, Chief Transformation Officer at Thredd, and hosted by Adam Bowman, Associate Practice Director at La Fosse, the conversation covered two hours of honest, experience-led discussion on one of the sector’s most pressing leadership challenges. 

The question at the centre of it: how do you lead when transformation never stops? 

Key takeaways

  • Transformation has become an operating condition, not a programme – the challenge is now governing perpetual change without overwhelming the organisation 
  • Boards and ExCo need interim milestones and rolling value demonstrations, not end-state reports 
  • Leadership alignment – particularly at CEO level – is the single biggest determinant of transformation success 
  • Change fatigue is real, and celebrating progress matters as much as hitting targets 
  • AI is reshaping transformation roadmaps fast, but governance and data foundations need to come first 
  • The most effective transformation leaders adapt to the culture they are working in, rather than imposing a single approach 

 

Transformation is now an operating condition

The room quickly arrived at a shared starting point. Transformation, as a concept, has changed fundamentally. What was once a bounded programme with a clear brief, a defined budget and a finish line has become something closer to a permanent state of the business. 

As Mark put it: “Transformation is where you suddenly have one pool of resources doing everything. You have one organisation trying to get to loads of different endpoints. But you can’t prioritise or juggle where you are.” 

Cloud migrations, platform overhauls, data modernisation, AI adoption – none of these initiatives exist in isolation, and none of them have a clean end date. They run in parallel, they interact, and they evolve. Leaders in the room described managing four or five concurrent transformation pillars, each with its own stakeholders, its own politics, and its own pressure to show results.
 

The challenge, the group agreed, is not delivery. Most people in the room had spent careers learning how to deliver. The challenge is governance: how do you sequence, prioritise and sustain perpetual change without the organisation – or the leadership team – burning out or losing the thread? 

The ExCo alignment problem

If there was one theme that ran through almost every contribution, it was this: transformation succeeds or fails at the top. Not in the programme office, not in the delivery teams – at ExCo level, and specifically with the CEO. 

“If the CEO is not strong enough to say, this is what we need to do, this is the priority, we funnel everything through here – then they are always going to bounce around their priorities,” Mark observed. “It will get delivered. But it will be like landing a plane on a wing and a wheel.” 

Leaders in the room described a familiar dynamic: ExCo members who are theoretically aligned, but who make competing decisions outside of formal forums in response to the loudest customer, the most urgent regulatory requirement, or the most visible short-term opportunity. The result is constant re-prioritisation, a team that stops believing in the plan, and a transformation that keeps moving but never quite arrives. 

One leader described what happens when priorities shift too often: “The staff just got to a point where they were like, there’s no point really focusing on that. Because next month it’s going to be something else.” 

The solution the room kept returning to was not consensus – several leaders were sceptical of consensus-driven decision-making – but clear, committed, top-down direction. “Sometimes you’ve got to be able to make decisions quick and sharp and live by them,” one participant said. “Collective is fine, but you’ve got to do something. The yo-yo between the two is what kills you.” 

Making value visible before the end state

Boards in financial services are under pressure to see returns. And increasingly, they are not willing to wait for a multi-year programme to land before they expect evidence of progress. 

The room was clear that this is actually a design problem, not just a communications problem. Transformation programmes are still too often structured around an end state that keeps moving – which means that interim progress is invisible, and leaders are constantly defending a programme that appears to be perpetually in flight. 

“Boards and investors focus on milestone outcomes in a roadmap. They don’t focus on the challenges in between,” Mark noted. “They’re entering milestones at a board level, not what I would call interim milestones at a transformation level.” 

Several leaders described shifting their approach: building rolling value demonstrations into the programme design, anchoring releases to tangible business, risk or cost outcomes, and being explicit about interim wins rather than deferring all narrative to the finish line. 

The conversation also touched on how programme reporting itself can undermine trust. Red-amber-green dashboards that trend green at year end – conveniently aligned with bonus cycles – were called out directly as a behaviour that erodes credibility with boards over time. “Transparency was like: it’s okay to be red when you’re red. Be green when you’re green,” one participant said. 

Celebrating progress, not just outcomes

Linked to the value visibility challenge was a simpler and more human point: leaders in continuous transformation environments are not celebrating enough. 

Multiple people in the room described programmes where teams had worked nights and weekends to deliver something significant – and received no acknowledgement, because the milestone was seen as the baseline expectation, not an achievement. Over time, this erodes engagement and accelerates the change fatigue that transformation leaders are already fighting. 

“You don’t celebrate the little wins along the way,” one leader observed. “You’ve got this end goal, and you feel like you’ve failed if you don’t get there. But you forget you’ve achieved 75% of it, and people stayed online over the weekend to get you there.” 

The group agreed that this is a leadership behaviour, not a programme management issue. Building recognition into the cadence of a transformation programme – not just at go-live moments – is as important as any governance structure. 

AI is reshaping the roadmap

No conversation among senior technology leaders in 2026 avoids AI. This one was no exception. 

Several leaders described transformation roadmaps that had shifted significantly in the last twelve months as AI capabilities evolved faster than anyone had planned for. “We’ve changed our programmes probably 50% in the last 12 months,” one participant said. “If I’d sat there 24 months ago and said this is my two-year plan, it just doesn’t look the same.” 

The room was pragmatic rather than evangelical. AI is creating real opportunities – and real risks if governance is not in place first. One leader described implementing a centre of excellence, establishing a usage policy aligned to data privacy governance, and only then encouraging broader adoption. “It’s boring stuff to sell,” they acknowledged. “But eventually it takes you to a safer place.” 

The broader point was one the group had already been circling: you cannot separate AI adoption from your transformation programme. It is part of the same continuous change that leaders are already navigating – not a separate workstream, and not a shortcut. 

What good looks like

The conversation closed on what effective transformation leadership actually looks like in this environment. Not a methodology, not a framework – a set of behaviours. 

A clear north star that the CEO owns and defends. Rolling value demonstrations that give boards and stakeholders something to hold onto. Governance that is honest rather than optimistic. Recognition built into the rhythm of delivery. And the flexibility to adapt the approach to the culture of the organisation, rather than imposing a single model. 

As Adam reflected: “We talk about technology unlocking potential. But it is the people around the table who determine whether the technology works and whether the transformation succeeds.” 

If you are a senior transformation leader in financial services and would like to be part of the next conversation, get in touch with Adam to learn more.