Why enterprise application strategies fail

Ineffective leadership

Implementation of enterprise applications often fails because there’s no clear leadership driving the change. Without a strong vision for change and leaders actively championing it, confusion often takes hold.

End users and key stakeholders may resist new applications, particularly when the benefits are unclear or the change feels disruptive. In these situations, poor leadership creates an environment of uncertainty, where teams struggle to align on key milestones, timelines and budgets. 

It’s important to invest in change management from the outset. Appoint a dedicated resource to lead stakeholder engagement, communicate the scope and impact of the transformation and create alignment on why the change is happening.

Additionally, conducting a formal change readiness assessment provides an opportunity to validate key deliverables, assess whether the proposed strategy is fit for purpose and highlight any early signs of resistance or confusion among stakeholders.

Strong leadership is about building trust, which happens through ongoing communication and honest feedback loops. It’s important to seek input from the wider organisation to keep the strategy grounded and supported.

Poor communication

Poor communication is one of the most common reasons enterprise application strategies lose momentum. Stakeholders (including external partners) interpret priorities, outcomes and success differently than the enterprise application team. Without clear and consistent communication, these differing perspectives can quickly lead to misalignment, confusion and delays in decision making.

Assess the stakeholders who need to be involved, what their priorities are and how they define success. Establishing a clear governance model is also essential in addition to creating a structured forum where stakeholders can align, contribute input and stay informed throughout the project.

Equally important is a tailored communications plan to outline key messages, milestones and timelines. Combining broad updates with interactive sessions helps to build trust, uncover concerns and increase buy-in ahead of any implementation.

Underestimating resources

Many organisations underestimate the resources required to successfully implement an enterprise application strategy. Budget constraints, misalignment with broader business objectives and failure to dedicate full-time staff to a transformation can be problematic.

This is compounded by ineffective vendor selection and management. Vendors and system integrators play a critical role in implementation, but unclear requirements and poor expectation management often lead to delivery gaps, under-resourcing and blown out maintenance costs.

To overcome these challenges, leaders must involve cross-functional teams early in the planning process to understand what internal resources are available to support the transformation. Employees who are engaged from the outset are more likely to take ownership and contribute actively.

Vendor management must also be treated as part of the implementation process, particularly for core systems like enterprise resource planning (ERP). Clearly defining business and technical requirements, including security and compliance, helps vendors understand how their solution fits into the broader strategy. This also means setting clear success metrics – and equally, defining what failure looks like.

Ignoring external factors

No matter how well planned an application strategy is, it’s almost guaranteed that some unforeseen circumstances will crop up and impact its transformation.

For example, vendors shifting to cloud-first models, regulatory and policy uncertainty, or security breaches causing downtime can quickly derail the most carefully designed initiatives.

Many organisations fail to anticipate these disruptions, only recognising their impact when things go astray. It’s a good idea to conduct a premortem that focuses on possible outcomes based on likely scenarios of failure. This allows teams to identify likely challenges, develop mitigation strategies and monitor risk throughout delivery.

While it’s important to have a plan, it’s also important to remain flexible. A resilient enterprise application strategy is one that can adapt to and not just react to change.

Neha Ralhan is a senior principal analyst at Gartner, advising organisations on ERP strategies