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5 challenges to Business IT Transformation

Technology is a critical driver of growth and success. As businesses strive to stay competitive and relevant, the process of transforming their IT infrastructure and operations becomes essential. However, this transformation journey is not without its challenges. In this article, we will explore five significant challenges that organizations face when undergoing IT transformation and discuss strategies to overcome them.

legacy infrastructure

1. Legacy Systems and Infrastructure

One of the most common challenges in IT transformation is dealing with existing legacy systems and outdated infrastructure. Many businesses have invested heavily in their IT systems over the years, making it difficult and expensive to migrate to modern technologies seamlessly.

Solution: A phased approach to migration is often the best strategy. By gradually integrating new technologies and platforms while maintaining critical legacy systems, businesses can minimize disruption and ensure a smooth transition. We have experience in planning and managing data and platform migrations, hardware and software deployment strategies, while mitigating risks and containing costs. Let’s discuss your next project.

cybersecurity and data privacy

2. Cybersecurity Risks and Data Privacy

In an era where cyber threats are constantly evolving and becoming more sophisticated, ensuring the security and privacy of data during IT transformation is paramount. The interconnectedness of modern systems makes them susceptible to cyber-attacks, putting sensitive information at risk.

Solution: Incorporating robust cybersecurity measures into the transformation plan is crucial. This includes regular security audits, employee training, encryption, and compliance with data privacy regulations like GDPR or HIPAA to protect sensitive data effectively. You need an experienced partner to help you avoid the legal pitfalls. This goes beyond the old days when “pen testing was enough. We have deep experience in regulations, data privacy, even Personal Cardholder Information (PCI) protection. We also provide employee online, on-demand training on cybersecurity awareness and more.

skill gaps and workforce training

3. Skill Gaps and Workforce Training

Adopting new technologies often requires a skilled workforce capable of understanding, implementing, and managing these advancements. However, the shortage of talent with the necessary skills and knowledge is a significant obstacle to successful IT transformation.

Solution: Businesses should invest in training programs for existing employees or partner with educational institutions to bridge the skills gap. Collaborating with tech-savvy consultancies can also provide valuable expertise and guidance throughout the transformation process. See our article Why Companies Should Outsource Training: A Comprehensive Guide to better understand partnering with us gives you time to focus on your core business, not on training. We develop specific courses to help with employee onboarding and skills training. We provide Learning Management Systems (LMS) and develop the courses that are role-specific for employee success.

integration and interoperability

4. Integration and Interoperability Issues

Achieving seamless integration and interoperability between various systems, applications, and devices is a major challenge during IT transformation. Incompatibility issues can lead to inefficiencies, data silos, and a fragmented IT environment. This could include marketing data in one system, but client or patient information in another.

Solution: Prioritize compatibility and interoperability when selecting new technologies. Work closely with vendors to ensure that the chosen solutions can integrate seamlessly with existing systems. Additionally, establishing clear integration strategies and utilizing APIs can facilitate smoother integration processes. When any implementation is considered, you need someone with requisite experience to ensure a smooth transition, someone who doesn’t take a “flip of the switch” approach, but understands testing in multiple models so there are no surprises when you go live. We have worked on projects for small companies to Fortune 500 companies, give us a call to see how we stand apart with experience and your best interest at heart.

cost and budget constraint

5. Cost and Budget Constraints

IT transformation can be a significant financial investment, from acquiring new hardware and software to training employees and maintaining ongoing operations during the transition. Managing costs and aligning the transformation with the budget can be a significant hurdle.

Solution: Conduct a thorough cost-benefit analysis to determine the ROI of the transformation. Develop a realistic budget and ensure that all stakeholders are aligned with the financial implications. Consider leveraging cloud solutions and as-a-service models to optimize costs. If you are managing on-premise and multi-cloud solutions, we can help you consolidate, manage and economize multiple vendors for cost savings and efficiencies. While we have experience with multimillion dollar budgets, we still understand every level of business has a budget to work within.

Less IT. More Business. Ask us how.


In conclusion, IT transformation is a fundamental component of modern business strategy, and overcoming the associated challenges is crucial for long-term success. By addressing legacy systems, enhancing cybersecurity, investing in workforce skills, focusing on integration, and managing costs effectively, organizations can navigate the digital landscape with confidence and resilience. Embracing these challenges as opportunities for growth will ultimately lead to a more agile and competitive business environment.

Have an upcoming project? Considering outsourcing some or all of your managed IT? Call us today to set up a free 30-minute discovery session. Our three core specialties are Managed IT, Marketing and Training. Call today to see how we can add to your bottom line and build value for your organization. Again, the call is free, what do you have to lose?

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  • Smith, J. (2019). “Legacy System Modernization: The Business Case for Legacy System Transformation.” Gartner.
  • Cybersecurity and Infrastructure Security Agency (CISA). (2021). “Protecting Against Ransomware.”
  • LinkedIn Learning. (2020). “Closing the Skills Gap.”
  • Gartner. (2021). “Magic Quadrant for Enterprise Integration Platform as a Service.”
  • Deloitte. (2018). “2018 Global CIO Survey: Manifesting Legacy.”
William R. Wheeler, CEO/Principle Consultant

William Wheeler is a consultant, storyteller, teacher and IT expert. He has been a national subject matter expert for several universities and has written dozens of college level courses and is a published author.

William R. Wheeler, CEO/Principle Consultant

Wheeler Management Group

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