If you’re a transformation or project manager, chances are you’ve already come face to face with the joys of legacy systems. They lurk behind critical processes, often undocumented, poorly understood, and frustratingly resistant to change. And while the brief might be all about moving forward — cloud, digital, agility — you know you can’t do that properly without dealing with what’s already there.

Here’s the challenge though: legacy systems are rarely just a technical issue. They’re wrapped up in people, processes, politics, and sometimes a fair bit of fear. So if you’re building a team to lead meaningful transformation, you need more than just strong delivery skills. You need the right mix of experience, perspective, and courage to take on what many quietly avoid.

A good starting point is asking yourself: do I have people who truly understand how these systems operate, both technically and operationally? That knowledge is often buried deep in one or two long-standing employees or spread thin across legacy contracts. Without that insight, you’re flying blind. Could you bring in someone who’s done this before in another organisation — someone who knows how to ask the right questions and map out what’s really going on under the hood?

Then there's the future-focused side. Do you have enough digital expertise to challenge old assumptions and spot opportunities? Someone who’s not afraid to say, “Why are we still doing it like this?” Equally, who’s acting as the bridge between the two worlds — someone who can translate legacy into future state, and bring the business along for the ride?

One of the biggest risks in legacy-heavy environments is letting the tech define the strategy, rather than the other way round. As a transformation lead, you’re in a unique position to flip that dynamic. But only if your team has the confidence and credibility to influence across departments, challenge the status quo, and navigate the inevitable resistance.

Another thing worth considering: who’s got the emotional intelligence to handle the people side of change? Legacy systems aren’t just systems — they represent years of investment, career-defining projects, and in many cases, the comfort zone of senior stakeholders. You’ll need someone in your team who can build trust, understand the sensitivities, and still keep things moving.

It’s easy to assume legacy systems are just a constraint you have to work around. But the right team can actually turn them into a source of insight — a way to understand where the organisation’s been, and what needs to shift to get it where it wants to go.

So, if you’re shaping your transformation team right now, ask yourself: do you have the right mix of legacy know-how, digital vision, and leadership resilience? And if not, what would it take to get there?

At Malikshaw, we work with transformation leaders across industries who are building exactly these kinds of teams. If you’re facing this challenge and want to compare notes — or need someone who’s been through it before — we’d love to hear from you.

What have you found most difficult about managing legacy systems in transformation? Who made the difference on your team?