Skip to content
city street with construction sign at night
AdvantageJun 11, 2025 9:00:00 AM5 min read

What's Holding Your Enterprise's Digital Transformation Back?

Let’s face it: most enterprise digital transformations don’t go smoothly.

Committing to digital transformation is like committing to a relationship: it requires dedication, vision, and the right partner. Serious roadblocks—from talent shortages to security setbacks—threaten that relationship, undermining transformation efforts via delays or outright failures. 

Multilocation environments multiply complexity and complicate execution processes, amplifying those already significant enterprise digital transformation challenges.

Thankfully, these challenges aren’t insurmountable, and organizations can transform successfully. But to overcome these obstacles, leaders must understand common roadblocks to change, identify pathways to success, and develop the right capabilities. 

This article provides information crucial to completing these tasks, revealing the six primary reasons digital transformation efforts fail and presenting actionable insights to avoid the same fate.

Roadblock Party: Key challenges to enterprise digital transformations

Let’s discuss the most common reasons digital transformations get delayed, underdeliver, or fail outright.

1. The business lacks strategic vision

A strategic vision includes well-defined goals, objectives, and an actionable roadmap aligned with the overarching business strategy. Lacking one is an all-too-common enterprise digital transformation challenge with devastating effects.

As McKinsey states, a clear digital transformation strategy is critical for organizations to survive. 

When leaders don’t determine desired outcomes and outline the tactical steps necessary to achieve them, they struggle to execute. Teams don’t have consistent direction, making stakeholder and employee support across diverse locations less likely. Wasted resources, bad decision-making, and complacency also emerge as unwanted impacts.

Actionable insight: Cultivate clarity with a strategic roadmap.

To survive (and thrive) throughout digital transformation, define and clearly articulate an overarching vision that resonates across all enterprise levels. It should be a blueprint for change that incorporates:

 

2. Internal stakeholders won't commit

Global enterprises need senior leadership across IT, operations, finance and marketing to buy in.

If leaders won’t champion change aligned with the overall vision, their teams won’t work effectively or passionately. Uncommitted stakeholders also lead to siloed decision-making, conflicting priorities, and misaligned or misguided efforts across regions. These outcomes result in inefficient resource allocation, low ROI, and delays.

Actionable insight: Foster executive sponsorship and cross-functional collaboration

Cultivating stakeholder commitment leads to executive sponsorship, which increases alignment and engagement. Creating an open, interconnected communication culture, encouraging cross-functional collaboration across all levels and locations, is also key. Think improved decision making, higher engagement, and expanded innovation capacities.

Foster executive sponsorship and cross-functional collaboration by:

  • Building great relationships with leaders 

  • Involving executives in strategic planning

  • Cultivating accessible communication channels

  • Equipping leaders with tools to build a transparent culture

  • Reinforcing shared responsibility

 

3. Teams lack the right talent

The IT skills gap is growing. There is a shortage of talent with crucial digital skills and expertise, from data analytics to cloud computing. As a result, global organizations struggle to find and retain specialized talent across locations. 

Companies operate at a massive disadvantage without the right people. Talent shortages cause delays, implementation issues, and project failures. So, it’s no surprise that the World Economic Forum’s 2025 report found that skill gaps are categorically considered the biggest barrier to business transformation.  

Actionable insight: Develop robust upskilling and hiring programs

To overcome this difficult enterprise digital transformation challenge, upskill existing employees and hire strategically.

Strategies for upskilling include sponsoring certifications, creating internal training courses, and developing mentor programs. Ways to attract and hire the right people include offering competitive packages, working with recruiters, and streamlining hiring. Methods for retaining that talent include supporting work-life balance and fostering autonomy.

 

4. Legacy systems, data silos, and IT debt slow the process

Outdated infrastructure, disparate data sources, and applications that are difficult to integrate with new tech across sites all interfere with transformations. Sprawling global enterprises deal with incredibly inconsistent tech stacks and exceedingly complex integrations, further complicating processes.

Actionable insight: Modernize systems strategically

With the right approach, overcoming this challenge to enterprise digital transformation and modernizing even the most complex frameworks is manageable. Follow these tips to release IT baggage and ensure successful transformation:

  • Thoroughly assess legacy frameworks

  • Update systems in phases

  • Meticulously back up all data and systems

  • Standardize tools and platforms 

  • Ensure scalability by aligning upgrades with long-term goals

  • Leverage middleware like APIs and connectors

5. Leaders face security setbacks and compliance concerns

Modern tech solutions bring new risks, generating novel enterprise digital transformation challenges. Diverse and potentially conflicting regulations across regions make navigating transformations even trickier for multilocation organizations.

Due to valid concerns surrounding these complex cybersecurity and regulatory compliance challenges, many enterprises hesitate to adopt new technologies. This hesitation holds teams back from implementing long-lasting change.

Actionable insight: Holistically bolstering security and compliance

Mitigate these concerns with robust security frameworks and compliance strategies. Secure frameworks feature:

  • Protective architecture

  • Automated monitoring

  • Centralized security dashboards

  • Strict access management protocols

  • Continuous audits, testing, and updates

  • Robust encryption across platforms, channels, and devices.

Airtight compliance strategies include:

  • Creating standardized documentation

  • Developing incident response plans

  • Checking regulations regularly

  • Vetting external providers 

  • Training employees continuously

6. The investment doesn’t match the initiative

IBM’s 2025 CEO Study revealed that 67% of CEOs need more budget flexibility to take advantage of digital opportunities driving long-term growth and innovation.

Many leaders of global organizations experience difficulties demonstrating a clear ROI for digital transformation initiatives and securing sufficient funding. This makes justifying investments, especially across numerous locations with varying needs and goals, a primary enterprise digital transformation challenge. 

Actionable insight: Develop an airtight business case

If leaders demonstrate a digital transformation investment’s undeniable value, stakeholders can’t say no. By creating a detailed plan exhibiting a project’s positive impacts and alignment with overall goals, teams can obtain the funding they need to execute initiatives.

To create one, teams should:

  • Track relevant KPIs 

  • Demonstrate long-term cross-functional value

  • Accurately calculate ROI

  • Clearly outline resource requirements

  • Illustrate how the project addresses organizational pain points

Conclusion: Don’t fall behind in the digital evolution

The road to business evolution is littered with formidable challenges to enterprise digital transformation. Many organizations get stuck due to talent shortages, outdated systems, or disengaged stakeholders. Others stall because of insufficient investments, unclear strategy, or security issues. 

Overcoming these roadblocks isn’t easy, but it’s possible. The right strategic partner significantly boosts your chances of success, reducing complexity and helping you execute in alignment with your goals.

At Advantage Communications Group, we specialize in guiding multilocation enterprises through digital transformation journeys. Our tailored solutions and support empower teams to navigate change with clarity, efficiency, and agility. 

The digital evolution won’t wait, so neither should you. Contact our experts to start unlocking your organization’s full potential today.

 

Recommended reading (Helpful links)