Livestream review: highlights from the ‘Stop creating a monster: how to slay system migration demons’ webinar

November 13 2025

Legacy technology is the monster hiding under the bed for many financial institutions. We all know it’s there, but are often too afraid to tackle it. Instead, we procrastinate, opting to bolt on shiny new applications that create layers of complexity, risk and “technical archaeology” – an approach that can drain both budgets and innovation.

We explored this vexed theme in our recent webinar, Stop creating a monster: how to slay system migration demons. Rich in practical insights on how to finally dispose of the legacy beast, the session featured four industry veterans who’ve been there and done it: author, seasoned tech executive and banker in recovery Leda Glyptis, Iliad Solutions’ CEO Anthony Walton, Philip Benton, Lead Analyst – Payments at Swift, and Andi Howkins, Chief Revenue Officer at Shieldpay.

Here are some highlights of this very engaging and useful discussion.

We all talk about innovation, but why is the industry so fearful of moving off ageing systems?

Leda Glyptis: “We as an industry are afraid of migrations… we accumulate the shiny things that eventually become legacy things, and we accumulate legacy things that historically become archaeology. We accumulate operating risk and complexity alongside all that.”

The point is, we’re culturally “additive” – the financial services industry is good at innovation and moving forward with new tools but is perhaps less good at moving off outdated tools. This is often because a full migration is seen as a career-ending risk. But since we can’t avoid it forever, we must learn to do it better.

Everyone has FOMO or the fear of missing out – the fact that everyone now has an AI strategy is evidence of this. But what’s the reality for most firms still running on legacy systems?

Philip Benton: “I don’t think FOMO is a good thing… It’s healthy to make sure you’re engaged in what’s going on, and you’re acknowledging that this is the way things are heading. But the reality is, things haven’t moved on just yet.”

Philip’s dose of reality reminded the audience that while hype is pervasive, real industry adoption (like the multi-year ISO 20022 migration) is gradual, deliberate and often community-driven. The real focus shouldn’t be about competing on the underlying infrastructure itself, universal standards need to be adopted, but on competing at “the edges” to serve the customer-facing use cases that this new infrastructure will eventually enable.

Many migrations fail before they even start, getting stuck in multi-year planning cycles. How do you overcome this “analysis paralysis”?

Andi Howkins: “Perfection is a myth – and our enemy… Action actually trumps inertia every time.”

Andi was clear that seeking a “foolproof” plan is a trap. The real risk is standing still. “Atrophy is our enemy. If we do nothing, then we are regressing… doing nothing is absolutely the worst thing you can do. And it’s, in fact, a backwards step.” The key is to define the “what, why and who” at the outset of a migration and then get started, iterating as you go.

If “perfection is the enemy”, what does a more practical, iterative approach actually look like?

Anthony Walton: “I’m a big fan of the 80/20 model… I started working with this if we could do 80/20 twice, and we called it 80/20 squared… if we can take that 80 percent we have 20 percent left, and then we do 80 percent of that, we’re kind of up to 96 percent within two iterations.”

Instead of trying to achieve 100 percent (which is often impossible), this iterative mindset makes a massive, complex project feel manageable and less “scary”, allowing teams to slay the “monsters” one at a time.

Finally, with all this focus on back-end systems, how do we ensure we’re doing this for the right reasons?

Andi Howkins: “A line of data is not just a line of data. It represents a real person, and the ability we have to positively impact the life of that individual represents our obligation to see past the data.”

This reminder of “why migrate” isn’t just about technical debt; it’s about building a foundation that allows you to serve customers better, faster and more safely.

Want to learn more?

The full discussion was packed with more practical advice, including how to identify the true “catalyst” for change, how to secure a budget for “boring” projects and how regulatory change is both a driver and a de-risker.

To hear all the insights from Leda, Anthony, Philip and Andi, watch the full Stop creating a monster: how to slay system migration demons webinar on catch-up here.


Get in touch