Even if your organization hasn’t embarked on its digital transformation, you’ve likely heard the term and considered whether a transformation is the right next step. So what is it, exactly, and what can a digital transformation do for your business?

A digital transformation usually refers to rethinking your approach to technology usage in the face of changing customer expectations or business objectives. For most businesses, this means implementing digital technologies across all aspects of the organization. There are many benefits to making this change. Some of the most notable benefits include using data-driven insights to provide better customer experiences and boost operational efficiency.

But to experience those benefits, you’ll first need to face the challenges that come with overhauling many of your current processes and legacy systems. Here are some of the top digital transformation challenges and what you can do about them.

Challenge #1: Lack of IT Resources

A successful digital transformation involves more than just strategy and planning. To ensure your company’s digital technologies are set up correctly and securely, your business needs a team of IT experts.

However, businesses are facing increasing difficulties in putting these teams together. With more and more companies everywhere pursuing digital adoption, a workforce shortage is developing, and many companies are struggling to find the expertise they need in key areas, including cybersecurity, enterprise architecture, and advanced data analytics.


Rather than navigating a labor deficit and trying to bring in new employees, businesses can instead outsource their IT talent for a highly cost-effective and efficient way of filling in any skill gaps. By bringing in an IT service provider like AccountabilIT, organizations get access to modern solutions and a team of IT experts with years of expertise helping businesses through the digital transformation process.

Challenge #2: Cybersecurity Concerns

When it comes to adopting new technology and processes, data security is naturally a top concern. Digital transformation typically involves shifting an organization’s security solutions to the cloud and moving all data to a centralized location, so it’s fair for business leaders to have their hesitations.

However, overcoming these potential trouble spots is one key to a successful digital transformation.


Digital transformation is most risky when an organization doesn’t have the expertise to properly set up and manage new systems. The best solution often involves bringing in an outside team of cybersecurity experts that can guarantee a successful and secure migration and, in many cases, stick around to oversee the ongoing management of your business’s cybersecurity. *Claire: add more here*

Challenge #3: Poor Change Management

It’s easy to assume that digital transformation is all about technology, but in reality, your organization’s people and processes are just as important, if not more. However, managing company-wide changes is not an easy feat. Inefficient business processes, inflexible or ill-informed decision-makers, and failure to communicate with employees can cause your organization’s digital transformation efforts to fail.


Simply put, you need to prioritize developing a robust change management strategy. In general, this should involve:

  • Proactive employee training: Beyond receiving clear communication about organizational changes, employees need the knowledge to adapt to new tools and processes. Otherwise, you might experience pushback or lack of participation.
  • Leader involvement: If your leaders don’t understand or support the why and how of your digital transformation, neither will your employees. Company leaders across various departments should be involved in your change management to ensure everyone is on the same page and ready to embrace your business transformation.
  • Cultural changes: Can your business’s culture embrace new ways of working? How much risk is it able to tolerate? Tuning into your current company culture while developing your strategy will prepare you for changes and encourage agility and adaptability.

Challenge #4: Your Digital Transformation Budget

While worth the investment, a digital transformation is not a cheap undertaking, and for companies with poor transformation strategies, the costs can become a barrier. Setting a budget itself can be an overwhelming challenge, given the scope and complexity of digital transformation.


To be successful, you need to develop a long-term digital transformation strategy with your budget front of mind. With a complete understanding of your goals, priorities, and what you’re hoping to achieve from your digital transformation, you’ll better understand where to allocate more capital. Part of your strategy may include setting a flexible budgeting model to accommodate the many other digital transformation challenges that are likely to come your way.

Challenge #5: Unclear Digital Transformation Strategy

Digital transformation is a trending term that can push businesses to embark on a journey for which they aren’t prepared. This lack of clarity on where your business is going, and what it takes to get there, can prevent your digital transformation from achieving long-term success.


You want to give your digital transformation initiatives the best chance to succeed. To do that, you need a clear transformation strategy. Here are some key questions you should be asking yourself when developing yours:

Does your strategy align with your priorities? You don’t want to transform your technology for the sake of transforming it. To create value, rather than more costs, you need to lay the groundwork and define your priorities, then build your strategy from there.

Is your approach holistic? The term is digital “transformation” for a reason. Instead of simply targeting the most urgent issues, your strategy should take a comprehensive approach to your technology journey.

Is your approach agile? Customer demands, and the technologies that support them, are constantly evolving. By making agility a core focus, you can better adapt to changes and ensure the success of your transformation.

Start Your Digital Transformation Journey with AccountabilIT

Ready to tackle the challenges of your own digital transformation? With our leading IT services, we’re here to deliver the strategic solutions you need. Contact us today to find out how our team of experts can help you carry out your digital transformation so you find long-term success.