In today’s digital business world, it’s become clear that if organizations want to remain competitive, digital transformation must become a part of their enterprise DNA. In other words, organizations can either become digital businesses or fizzle out.

A “digital business,” as coined by IDC in its 2023 CIO report, is a dynamic enterprise that continuously evolves its operating models and digital platforms. However, as critical as digital transformation initiatives are, McKinsey & Company reports that the risk of failure is 70%.

Scary, right? Fortunately, failed digital transformations share common pitfalls that we can learn from to increase our chances of success. Let’s dive into 7 of the common mistakes that cause digital transformations to fail (and how to steer clear of them!)

Top 7 Digital Transformation Mistakes and How to Avoid Them

1. Poor Change Management Efforts

Humans tend to fear what they don’t understand. As a result, when organizations’ change management strategies are insufficient, their employees resist new tools, upskilling initiatives, and processes. They might even fight back and actively undermine your progress out of fear of being replaced. This reaction could be due to staff not understanding why change needs to happen, what that change will specifically entail, or how it will impact them. It might seem obvious to you that your changes will positively impact your employees’ workdays, but it may be less apparent to them.

How to Avoid It

Before anything else, your employees need to understand your “why” or the reasons your organization is pursuing digital transformation. This is your opportunity to squash fear and beat the rumor mill and instead promote a clear, reassuring single narrative. Ensure that your employees understand the challenges and company losses that have made your proposed change necessary. Whenever possible, give examples that relate directly to the staff members you’re speaking to. For example, if your transformation will simplify and accelerate a tedious process that members of a certain department currently dread, tell them. On the flip side, be sure to highlight the benefits and how they will directly improve the lives of staff members. “What’s in it for me?” is a real concern, and the more personalized your messaging can be, the more you’ll hit home with your employees.

Along with the why, you need to be able to break down your training and upskilling plans and how they will personally affect each employee. This will help ease employees’ worries about job security and help them feel supported.

Additionally, your staff will need transparent, frequent communication from organizational leaders throughout your journey. Whether your initiative is experiencing a bump in the road, or you just celebrated a huge win, make your employees aware of it. And when victories arise, celebrate them with your employees. For example, many organizations set up fun rewards for when milestones are hit and create real-time progress charts to build anticipation as the company inches closer to reaching the goal.

2. Insufficient Training

Too often, organizations get overly confident in their new technology’s user-friendly interface and underestimate the amount of training that will be necessary. Careful training is vital for successful digital transformation. If staff aren’t confident in how to use new tools, they will find workarounds to avoid using them, or they may make mistakes that are time-consuming to fix.

How to Avoid It

Set yourself up for stellar user adoption by tailoring your training plan to your employees’ experience levels and learning styles. Learning a new tool requires staff to internalize a high volume of new information. Some employees will come in with technical expertise to pick up new solutions easily, while others will take longer and need some handholding. And to help them comprehend and retain this information more effectively, cater to a variety of learning styles by offering:

  • How-To videos
  • RPA-based in-application training
  • PDF guides and articles
  • Live instructional sessions
  • Small group collaborative learning

Don’t let training end with the go-live, either. Even when your team is comfortable using your new tool, you will need to keep them up to date on new updates and upgrades. Consider holding quarterly training sessions, creating a newsletter, and designating a location for your PDF guides and instructional videos.

3. Fear of Temporary Failure

The fear of temporary failure can significantly hold back a digital transformation’s success. If your employees feel they must avoid failure at all costs, they may stick to traditional methods and resist new tools or processes that could potentially result in temporary setbacks. They may also not feel comfortable voicing ideas for improving a new process or solution’s design. This limits learning opportunities and leads to innovation stagnation and indecision that can lose your company out on market opportunities.

How to Avoid It

Help your staff trade a rigid mindset for a continuous improvement mindset by fostering an innovative culture. An innovative culture embraces experimentation, encourages calculated risk-taking, and sees failure as an opportunity for growth. But to set the stage, you need to enable psychological safety. Your employees need to feel safe to speak up, fail, or present an out-there idea. Let it be known that ideas that start with “This might not work, but…” can be some of the most creative, innovative ones. Whether it turns into a learning experience or a smashing success, it’s worth trying. And when employees complete training and begin using a new tool, encourage them to look for opportunities to apply their knowledge and identify room for improvement.

4. Not Investing Enough

Everybody likes to save money, but when it comes to digital transformation, cheaper doesn’t necessarily mean better. If you focus too heavily on cost, you may underinvest, which will cause you to miss benchmarks along your digital transformation journey. Focusing primarily on cost may also lead to a narrow perspective that overlooks opportunities to seize new markets, improve customer engagement, streamline processes, and create value long-term. Organizations with their sights set on keeping the budget as tight as possible may also downplay training and change management initiatives, self-sabotaging even further.

How to Avoid It

When planning your digital transformation, take a people and process-first approach. The ideal plan and set of tools for you won’t necessarily be the cheapest but the ones that best fit your unique organization. Instead, take a holistic approach that balances cost considerations with strategic goals, long-term value, customer and employee needs, quality requirements, and process improvement. This comprehensive view will allow your organization to make smarter decisions that support sustainable transformation and growth. Additionally, performing a cost-benefit analysis can help you further ensure that you’re getting the best all-around deal that will support your company long-term.

5. Implementing New Technology onto Broken Systems

Shiny new technologies are exciting. But the trouble starts when you start buying neat solutions that lack a rock-solid business case for your organization. Things get even worse if you layer them onto broken processes, inefficient legacy systems, and employees who don’t want anything to change.

How to Avoid It

You can improve your digital transformation’s chances of success by using integrated strategies that begin with goal assessment and prioritize process improvement before you choose any tech. That means doing a comprehensive analysis of your existing systems and processes. Search for pain points and bottlenecks and consult the staff members who work with these processes regularly. And if you can tap into data using tools like process mining, even better! Bringing along an experienced digital transformation partner is also invaluable. These subject matter experts have seen it all and will work with you to ensure that your digital transformation plans and any tech investments are in line with your vision and goals.

6. Skills Shortage

Many organizations don’t properly assess whether they have the skills available to execute their transformation plans. Some simply lack the necessary capabilities. Others may have all the right resources on hand, but the skilled employees they have in mind lack the bandwidth to take on the work in addition to their “day jobs.”

How to Avoid It

If you have the skilled staff to make your transformation goals a reality, you’ll probably need to reprioritize their workloads. If you need offload some of their usual work to make it happen, you can hire additional staff, or skip the talent search by partnering with a managed services provider. Your managed services provider can offer you experts that can take over your digital transformation team’s typical work, or they can support your transformation efforts directly.

7. Failing to Take the Customer Along on the Journey

In addition to getting your employees on board with your digital transformation, you need to successfully reintroduce your new and improved business to your customers. Unfortunately, many organizations struggle here. For example, if a bank introduces a new app customers can use to manage their accounts, some orientation is needed. Too often, a company will assume that the new application’s interface is completely intuitive and fails to provide sufficient onboarding.

How to Avoid It

To take your customers along for the digital transformation journey, you should first establish clear, consistent communication channels to keep them informed about your transformation progress, how it’ll benefit them, and milestones. You can share this information via social media, website updates, or emails. Plus, you can seek customer feedback as you go. Doing so may let you in on clever ideas you wouldn’t have thought of otherwise, and it’ll make them feel valued. Finally, support your customers with training programs and support materials to help them adopt your change. Consider all the ways that the customer experience will change as a result of your transformation, and relay those insights through a webinar, video tutorials, FAQs, and live chat support.

Skip to the Good Part

Did you notice: Most of these mistakes aren’t directly tied to your choice in technology! That’s because almost all the time, your technology is just fine. It’s typically the lackluster change management, skillsets, training, and planning that get organizations into trouble.

You deserve a successful digital transformation that produces sustainable results and scales. With thoughtful, strategic planning, the right people, and knowledge of the lessons other organizations have learned the hard way, you can avoid the common pitfalls of digital transformation and reach your goals.

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About Kara

As a Naviant Content Writer since 2019, Kara is passionate about helping organizations unleash the power of technology to solve their business challenges. In her weekly articles, Kara breaks down the latest research, trends, and tips in the digital transformation world, specializing in intelligent automation, the cloud, AP & HR automation, artificial intelligence, change management, and more. She is also a Copywriter for the American Marketing Association-Madison, where she contributes bimonthly articles that interview industry experts and highlight the latest marketing trends. When she’s not writing, Kara is working on her latest art project, scoping out new music, or out for a run.