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Our Guide to Tackling Digital Transformation Roadblocks

Four things that stall a transformation programme — organisational resistance, data silos, legacy infrastructure and the skills gap — and what each one actually requires of your IT asset data before you can move past it.

Transformation programmes tend to fail for reasons that have nothing to do with the technology being adopted. They fail on the ground the programme is standing on: what people already own, what they already know, and what they are already being asked to do.

Certero’s consultants see the same four roadblocks come up again and again. None of them is exotic. All of them are cheaper to deal with before the programme starts than halfway through it.

Roadblock 1: Organisational resistance

The challenge

Transformation gives a business the chance to improve how it operates at a systemic level — from process design to how people are supported in their work. Decision-making gets faster and better informed. But the culture changes too, and that is the part nobody signs off in a business case.

Change reads as a threat to some people. It is unfamiliar and untested. That feeling does not park itself at the office door and wait for closing time.

What to do about it

Frame the changes positively but transparently, and give people the support they need to adapt quickly. Say why the change is happening and what the business gets from it. That part is standard.

The specific version of this problem inside IT is worth calling out. Your IT team has built up deep knowledge of how the organisation runs. Individuals own particular things — the application landscape, the infrastructure, the security posture — and their standing in the team is bound up in that ownership. Resistance often comes not from disliking change but from a reasonable fear of handing over understanding and control to a system nobody trusts yet.

Which is why the order matters: transform your understanding of your IT capability before you transform anything else. If the IT team is reliably informed, it can manage change with confidence rather than defend territory.

CerteroX is built for that. Five products — ITAM, SAM, SaaS Management, Cloud Management and AI Management — on one data model, so hardware, software, subscriptions, cloud resources and AI use are all described by the same schema rather than reconciled between four tools that disagree. One repository for asset intelligence means every department is arguing about decisions rather than arguing about whose export is right.

When you select a platform for this, bring multiple stakeholders into the evaluation. It is the only reliable way to test your real requirements against what a product actually does, and it buys you advocates rather than sceptics on day one. Leading a transformation across everything the business owns is a daunting task alone; make sure you have backing from the people whose teams it will land on.

Roadblock 2: Data gaps and silos

The challenge

A common problem is that the organisation genuinely cannot see where all its assets are. The data is trapped in disparate silos, which makes a holistic view impossible. Without the full picture you cannot make well-informed decisions, so the programme can find itself stuck before it delivers anything.

What to do about it

You need the visibility to be complete across all five asset classes, in one place. For larger organisations with more moving parts, this matters more, not less.

That means discovery that actually reaches everything. CerteroX ITAM runs ten discovery methods into one schema — native agent, command-line inventory, agentless, standalone for air-gapped systems, network scan, Active Directory import, third-party ITAM import, cloud and SaaS connectors, browser monitoring and file metering. The native agent covers six operating system families, including AIX, HP-UX and Solaris, which is where the “we didn’t know we had that” conversations usually start. There is no reconciliation project afterwards because there is nothing to reconcile.

Just as important: the position stays current rather than being assembled on request. CerteroX computes a continuous compliance and cost position instead of a point-in-time reconciliation, so you can track the programme as it happens rather than reviewing it retrospectively. Improvements get made while they still count.

Roadblock 3: Legacy IT infrastructure

The challenge

Transformation is about using new technology to improve everyday processes. If the organisation is weighed down by technical debt and infrastructure that cannot support what you are trying to do, you reach an impasse quickly. If the current technology cannot withstand the level of change you are aiming at, no amount of programme governance fixes it.

What to do about it

Moving off legacy systems looks daunting because of the volume of data they hold and the historical pain of implementation and configuration. Pushback from experienced users who have to learn new systems is a real cost too.

The specific problems legacy systems create:

  • Support and maintenance. Older systems get updated less often and carry weaker support.
  • Integration. Legacy systems frequently cannot integrate with the modern systems you are introducing, which quietly narrows the set of vendors you are able to choose from.
  • Data silos. As above, legacy tooling is prone to creating them, and they make a single view impossible.
  • Security. Infrequent updates make these systems an attractive target.
  • Hybrid coverage. Older ITAM tooling was built for on-premises hardware and software, and never extended properly to SaaS, cloud IaaS and PaaS.

That last point has changed since this was first written, and it is worth being precise about it. Hybrid coverage is no longer a gap in the market. CerteroX SaaS Management discovers applications through three converging signals — identity provider sync, vendor API connectors and a browser extension — which surfaces shadow IT and Shadow AI, not just the applications finance already knows about. CerteroX Cloud Management runs twenty-six named, individually tunable cost checks across twelve cloud and data platforms and ingests the FinOps Open Cost and Usage Specification natively. CerteroX AI Management governs models, experiments, GPU compute and AI seats as one asset class. If an ITAM platform tells you hybrid is on the roadmap, that is a statement about that platform, not about the problem.

There is also a straightforward upside. Where the destination is a cloud-based platform, the transition is usually far simpler than an on-premises migration. CerteroX is provisioned as SaaS, so the overhead of moving to a modern platform is a fraction of what it was when these tools shipped as server installs.

And there is a real benefit to your people when tasks previously spread across several old toolsets land on one platform: there is one interface to learn, and access to information goes up sharply. That makes your staff more versatile, because they can get at the tools and data they need with more autonomy and less waiting.

Roadblock 4: The talent and skills gap

The challenge

The last roadblock to prepare for is not having the skills you need. To transform successfully you have to bring in the right capability — by training existing staff, hiring, or working with external partners. Each route has different timescales, different costs and different risks, and the choice deserves more thought than it usually gets.

To make it concrete: suppose you adopt cloud services that promise to streamline your operations. In theory, excellent. But if nobody on the team is experienced in configuring and running cloud environments — and understands the financial processes and information security governance around allocating resources to departments — then nobody is actively managing the new arrangement. Cloud resources are notoriously easy to consume and costs get away from you quickly and quietly. The time, money and effort go in and the benefit does not come out.

What to do about it

Assess the position honestly. Work out which skills you have, which you need, and which you are pretending to have.

Where the gap is in IT asset, software, SaaS and cloud management specifically, it can be contracted rather than hired. Certero runs an in-house services team alongside the platform, so the licensing and FinOps expertise is available without a recruitment cycle. NHS South West London ICB’s ITAM Asset/PSL Manager, Reece Emson, describes what that compresses: “Certero’s SAM managed service allowed us to significantly mature our license posture at a fast pace, something that would have taken 3-4 years without their involvement.”

That is the general shape of the answer to all four roadblocks. None of them is solved by buying a tool. They are solved by knowing what you have, in one place, continuously — and then having someone competent read it.

Related reading

Other posts covering the same ground.

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  • Certero Insider Newsletter – September 2025

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