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7 Digital Transformation Challenges & How to Face Them

7 Digital Transformation Challenges & How to Face Them

By Dannah Cahn

Organizations contain dozens of rolls across different levels, from the mailroom to the C-suite. It only makes sense that with this many moving pieces, the process of becoming a technologically advanced business will have many hurdles to jump along the way.

1. Complexity

Most organizations have adopted the necessary technology at each new wave of tech improvements. You have laptops, ERP, CRM, and much more. Each department may use a different system for analytics, project management, prototyping, as well as other industry-specific digital tools.

But this causes complexity. Multiple systems have been layered on top of each other inadvertently reducing productivity. Keeping track of and logging into a different system for each and every business function overwhelms employees.

To overcome this digital transformation challenge, find ways to simplify and streamline your digital systems. This doesn’t necessarily mean getting rid of existing systems, but it definitely means gluing your systems together.

2. Digital Adoption

digital transformation challenges

Bringing on new tools means onboarding your employees. The digital transformation challenge here is emphasizing the second part of this equation: the employee. Successful digital transformation effort puts the human experience in the center of all processes.

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The decision to invest in a new tool is not one that was made by accident. You analyzed the data and decided that this was the best move for your business — to increase employee productivity or drive customer retention. Without true adoption or employee proficiency, you are failing to maximize the potential of your digital assets.

Digital tools tend to vary by interface, functions, features, and usage. It can not be assumed that employees will pick up the necessary skills based on experience with similar platforms. Training is a critical part of digital migration or implementation, as is ongoing support. Try using a Digital Adoption Platform (DAP) to accelerate onboarding and provide ongoing, contextual guidance directly on the application.   

3. Cultural changes

Digital transformation is more than just digitizing documents. This digital transformation challenge is about transforming the way you work and live to be digital first. Employees that used to spend a lot of time with customers, may now spend a lot of time with computers, and other ways digital transformation changes the culture of a workplace: collaborative working, self-service, transparency, etc. The natural human resistance to change is a challenge.

digital transformation challenges


Culturally, employees must rethink their role. Someone who once input data, might now be more valuable as a data analyst.

4. Pace

Another digital transformation challenge is keeping up with latest technologies, and on the other side of the coin, keeping up the number of transformations occurring internally. Today’s new challenges are in AI, ML, and IoT: how do we leverage those? The solution is staying one step ahead.

Anticipate automation by creating new roles where technology complements human work rather than simply replacing it. Rather than displace jobs, these new tools should pioneer a way to engage individuals and push collaboration with technology further.

Dream big. Create portfolios of potential ideas for the future state of your customer journey. This should allow your company to create and evaluate business hypotheses for new technologies and test them via customer research.

5. Competing priorities

When it comes to taking digital transformation steps, every department could benefit. You can only pursue so many initiatives at once without spreading your resources and focus too thin. The challenge is choosing which ones to bring to life. Remember, digital transformation is a marathon, not a sprint.

A good place to start is by studying the market to understand your customers’ unmet needs and where your competitors are failing to satisfy. This space is an opportunity to innovate and improve the customer experience through new technology.  

Staying on top of technological trends will also help you to gauge which ones are going to bring value to your business. This includes staying up to date on emerging technology as well as the relevant shifts in consumer behavior as it pertains to technology.

digital transformation

6. Security

Successful digital transformation requires a transformation of security as well. Some of the largest companies in the world have fell victim to cyber attacks. IP, personal information, and finances are at risk. In the digital world, contained enterprise networks of the past no longer exist. Security must be embedded directly into all applications.

Much like putting off an overdue doctor’s appointment, many companies choose to delay strengthening their security systems until it is too late. According to Gartner, through 2020, 99% of vulnerabilities exploited will continue to be ones known by security and IT professionals for at least one year. That means companies should first and foremost fix the vulnerabilities they know exist.

7. Defining Success

The productivity paradox, first articulated in the 1970’s, describes the phenomenon that despite the influx of computer technology, actual productivity was stagnant. If technology is supposed to make us more productive, why don’t we see gains in productivity? What studies have shown is that the way we measure productivity may be the problem.

digital transformation challenges

Before setting out on your digital transformation journey, sit down and define precisely what you wish to see by way of transformative efforts. According to a survey conducted by 451 Research and commissioned by CenturyLink Inc., top responses were: improving business agility, better risk management and improving operations agility.

Organizations must define what success is in digital transformation, but that alone is a huge challenge. What exactly are the success metrics for digital transformation? How does a business know when they have reached digital maturity?


Dannah Cahn
Dannah is a writer, creator and hot sauce enthusiast. Educated in communications, today she is the puppetmaster behind WalkMe’s content marketing strategy. From kale tacos to B2B content, Dannah’s creations share a signature spice.