Many companies have faced significant challenges since late 2019. These changes required them to rethink their operations and develop new strategies to serve and satisfy customer needs. Given the fact that organizations were not ready for such a pandemic, many businesses have to deal with unprecedented obstacles during the 2020 government lockdowns. 

Social distancing protocol, quarantine protocols, furlough, capacity regulations, travel restrictions, and layers are just a few of the problems that all business owners had to struggle with. 

One of the most challenging obstacles to managing an organization’s remote working environment was the lack of IT expertise. As more companies started adopting remote working practices, many executives realized their existing solutions were not up to par.

Will the trend continue into the new year? As we look back at 2020, some of the biggest challenges faced by the industry are expected to continue in 2021 as well. 

Before moving onto the challenges, if you are not aware of digital transformation, then check out this Digital Transformation Definition.

Top IT challenges of 2021 digital transformation initiatives

Since late 2019, the outlook on the world has had a dynamic change in all sectors, including business. The constraints faced by the businesses earlier was somewhat like this-

Top 5 General digital transformation challenges faced by different-sized businesses
Less than 100 employees100-1000 employees
  1. Limited budget
  2. Restrain from employees
  3. Lack of digitization initiative expertise
  4. Inept business partners
  5. No overreaching digitization strategies
  1. Faulty organizational structure
  2. Limited budget
  3. Lack of expertise in digitization initiatives
  4. No overarching strategy for digitization
  5. Pushback from employees
1000-1500 employeesMore than 5000 employees
  1. No overreaching digitization strategies
  2. Lack of lead in digitization initiatives
  3. Limited access to technical expertise
  4. Employee resistance
  5. Lack of budget
  1. Employee resistance
  2. Lack of lead in any initiative
  3. Lack of technical expertise
  4. Organizational structure gets in the way
  5. No lead in digitization initiatives

From the above table, you will notice that previously the businesses faced the same kind of digital transformation challenges regardless of their size. 

And even today, this hasn’t changed, but the nature of challenges has changed since the onset of the coronavirus pandemic.  

The following are some of the top digital transformation initiatives challenges that IT will face in 2021. 

  • Bridging the skill gap

It now plays a crucial role in businesses. Day-to-day operation depends on the capability of handling complex tasks to initiate digital transformation. Due to the increasing complexity of the industry’s tasks, it is becoming more challenging to find skilled and qualified individuals. 

As already predicted by Gartner, by 2020, more than 75% of organizations were experiencing visible business destruction due to skill gaps.

Through availing a staffing provider, businesses can get the resources they need across their entire IT department. They can also find candidates with a wide variety of skills and experience, and they stand behind their work. Also, by integrating automation into your workflow processes, you can help bridge the skills gap and save money on overhead expenses.

  • Managing Operations in a Remote Environment

The COVID-19 pandemic has compelled businesses worldwide to transition to an almost entirely remote workforce. Many company executives are still concerned about the logistics of keeping employees active while providing outstanding service to customers.

These businesses will have to devise a digital transformation plan to streamline their operations. Things like providing workers with the resources they need to be efficient and the tools to track that efficiency – will be critical, and customer service levels must be transparently monitored.

Organizations must also have the appropriate IT infrastructure, software, and processes in place to facilitate a virtual work environment, such as reliable VPN connections, sufficient bandwidth, BYOD rules, Virtual conferencing platforms, and other such things.

  • Protecting against vulnerabilities

Cybersecurity and data privacy have become more prevalent problems in recent years. Like the California consumer privacy act (CCPA) and EU general protection data regulation (GDPR), privacy laws have set standards for how businesses can interact with their data applicable to both consumers and organizations. Due to the rise of data breaches, companies have never been more critical to protect their sensitive consumer data.

A network assessment will help identify areas of weakness and suggest actions to minimize risks. By working with a managed IT services provider, you can rest assured that your network is secure and up to date. If you do not have the right tools in place to prevent and respond to a potential data breach, you may end up paying a high price down the road.

  • Facing Uncertainty with the Cloud

Many companies have recently introduced cloud solutions. Surveys predict that by 2022, up to 60% of organizations will use a cloud-managed service offering from an external service provider, double the percentage of organizations in 2018.

A cloud environment provides many advantages and can help improve business processes. If the company does not invest and manage its cloud migration properly, it may face drastic consequences.

During the COVID-19 pandemic, switching to a cloud solution was a perfect example of this. According to a report published in May 2020, COVID-19 is causing 40% of companies to accelerate their cloud migration.

Companies should review their data and workloads before considering a cloud migration to determine the costs and possible service impacts. It could be worth paying a little more upfront to save a lot of money later.

  • Implementing new technologies and strategies

It is almost impossible to choose the appropriate technology to incorporate into the infrastructure and IT strategy to remain competitive in the market. However, it is impressive to introduce well-planned new technology. It will raise the chances of a better return on your investment. 

Identify the technologies that would best suit your IT goals. Tools like gap analysis or site surveys to access the present IT business information system helps to pick out the suitable strategy and technology for you. Using a managed service provider could also help you deal with strategic and technological issues. 


Overall, ensure to start with a solid foundation – one that leads to a diverse and higher level of performance for your business, customers, and workforce.

Many of the advantages of a digital transformation are within reach with a mentality of constant development and creativity. Face the challenges when they arise and do the best to plan ahead of time.

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