11 Challenges (and Solutions!) of Digital Transformation

Digital transformation

Digital transformation is the process of using technology to significantly improve business processes by laying the technological framework needed to sustain long-term growth. It can bring many benefits to professional associations, but it can also present several challenges that must be solved to achieve successful implementation. 

Today, we’ll be looking at some of the key challenges of digital transformation for professional associations–and how you can solve them!

1. Legacy Systems

The Challenge: Professional associations may have legacy systems that are difficult to integrate with new technologies. This can make it challenging to modernize an organization’s IT infrastructure and implement new tools, such as learning management systems.

The Solution: Instead of attempting a complete overhaul of their IT infrastructure, associations should consider a phased approach. 

Start by modernizing one system or a set of related systems at a time. 

This allows for better resource allocation and minimizes disruption; it also enables the organization to learn from each phase before proceeding to the next.

2. Cultural Resistance

The Challenge: Change management can be a significant challenge for professional associations, as some members may be resistant to change or unfamiliar with digital technologies. This can make it difficult to gain support for digital transformation strategies.

The Solution: The answer lies in clear communication and transparency. 

Associations should ensure that the goals, benefits, and rationale behind their digital transformation initiatives are clearly communicated to all members and stakeholders. 

Provide regular updates on any and all progress, challenges, and expected outcomes. 

Transparency helps to build trust and understanding, reducing resistance to change.

3. Comfort with the Status Quo

The Challenge: Many people are comfortable with the way things are and may not see the need for change. They may also be hesitant to disrupt existing systems–even if they’re inefficient or outdated.

The Solution: Create a sense of urgency. Clearly communicate the reasons why change is necessary and the risks of maintaining the status quo. 

Highlight external factors (such as industry trends, emerging technologies, and evolving member expectations) that necessitate adaptation. 

By creating a sense of urgency, you can motivate members and stakeholders to embrace change and overcome their comfort with the existing systems.

4. Lack of Understanding

The Challenge: Sometimes, people may not fully understand the benefits of updating technology to reduce complexity. They may not see how it will improve their work (or the organization as a whole), leading to resistance to change.

The Solution: Clearly communicate the advantages of the transformation. Develop a comprehensive communication strategy to clearly outline the benefits of updating technology to reduce complexity; make sure to use concrete examples for the best results! Look into similar organizations and see how they have used digital transformation to thrive. 

Explain how the new technology will simplify workflows, streamline processes, and improve efficiency for staff, while improving the user interface and experience for members. Emphasize the positive impact transformation will have on the organization as a whole.

5. Fear of Failure

The Challenge: Changing processes can be risky, and some people may be afraid of failure or making mistakes. This fear can lead to a preference for sticking with what they know.

The Solution: Break the process down into manageable steps. By deconstructing transformation into smaller, more achievable steps, an association can reduce the level of risk and increase their likelihood of success. 

On the member side, a phased system of change allows an organization’s audience to build confidence as they learn the new technology. 

6. Inadequate Training and Support

The Challenge: If people don’t get adequate training and support when switching to new processes, they may be reluctant to change. They may also feel overwhelmed by the new technology and processes, making them hesitant to update.

The Solution: Develop comprehensive training programs that cover the new technology, processes, and any associated changes. 

Offer a variety of training formats, including workshops, webinars, e-learning modules, user-friendly documentation, and one-on-one coaching. Ensure that the training is tailored to different user roles (as well as for staff and for members) and skill levels, providing step-by-step guidance and practical examples. 

Consider also hosting dedicated support channels (such as a helpdesk, email support, or chat support) to address member questions and concerns promptly. 

7. Cost

The Challenge: Digital transformation can require significant investment in new technology and systems, which may be a challenge for associations with limited budgets. 

The Solution: Conduct a thorough cost-benefit analysis to determine the potential return on investment (ROI) of the proposed changes. Associations should identify the areas where their investments will have the greatest impact and align them with their organization’s strategic goals. This analysis can help prioritize investments and demonstrate the value of digital transformation to stakeholders. 

Next, explore funding opportunities through grants, partnerships, or sponsorships that specifically support digital transformation initiatives. Look for government programs, industry associations, or foundations that provide funding for technology upgrades or digital initiatives. 

Collaborating with other associations or organizations in the same sector may also provide cost-sharing opportunities.

8. Security

The Challenge: With more data being stored and transferred digitally, there will always be concerns about data breaches and cyber attacks. Professional associations must ensure that they have thorough security measures in place to protect their data and their members’ data.

The Solution: Conduct regular security audits and assessments to identify potential risks and address them promptly. These assessments will help point out potential points of vulnerability in an organization’s systems, processes, and infrastructure. Audits should also include an evaluation of network security, data protection practices, access controls, and compliance with relevant regulations.

Additionally, associations should educate staff and members about security best practices, such as strong password management, phishing awareness, and data protection protocols. Regularly conduct training sessions and awareness campaigns to keep security practices top of mind. 

9. Skill Gap

The Challenge: Digital transformation can require new skills that staff and members of an organization don’t possess yet. Associations may need to develop or hire new talent to support the transition.

The Solution: Conduct a thorough assessment of existing skills within the association to identify the gaps that need to be addressed. Determine the specific competencies required for successful digital transformation and compare them to the current skill sets of staff and members. This analysis will provide a clear understanding of the areas where additional training or new talent is needed.

Then, develop training programs to meet these needs. Offer a variety of learning opportunities (such as workshops, online courses, webinars, or mentoring programs) to help individuals acquire the necessary skills. 

Associations can even collaborate with external training providers or industry experts to deliver specialized training in areas such as data analytics, digital marketing, or technology implementation. 

Encourage continuous learning and provide ongoing support to ensure skill development.

10. Legal and Compliance Issues

The Challenge: Digital transformation may also bring new legal and compliance requirements that associations need to be aware of, such as data protection laws and regulations.

The Solution: Conduct an assessment to identify potential legal and compliance gaps within the association’s existing processes and systems. Associations can evaluate their data handling practices, consent mechanisms, security measures, and any other areas that may be impacted by regulatory requirements. This assessment will help identify areas that need attention and ensure compliance with relevant laws.

11. Stakeholder Management

The Challenge: Professional associations often have multiple stakeholders, including members, partners, and regulators. Managing the expectations and needs of these stakeholders during periods of digital transformation can be challenging.

The Solution: First, set realistic expectations with stakeholders regarding the timeline, outcomes, and potential challenges of the digital transformation process. Be transparent about any limitations or constraints that may affect implementation. Clearly communicate the benefits and value that the transformation will bring to stakeholders to gain their support.

Then, work on actively engaging with stakeholders to gather their input and involve them in decision-making processes wherever possible. Seek their opinions, ideas, and suggestions to shape the process in a way that everyone will be happy with.


When it comes down to it, the benefits of digital transformation far exceed their challenges. While making the change can be difficult, associations that implement digital transformation improve their ability to engage members, deliver value, and drive growth. 

Take the plunge and discover how your association can start the process today!