5 Digital Transformation Challenges and How to Overcome Them

Digital transformation has been happening since the personal computer was invented and was turbocharged when the internet came along, as people were able to communicate instantly across the globe. The “cloud” was the next big revelation, as teams worldwide could access their data securely no matter where they operated. Fast forward to 2020, and the pandemic forced many organizations to shift how they worked together overnight as digital transformation came to the forefront once again.

McKinsey notes that responses to the pandemic have sped up the adoption of digital technologies by several years and that many of these changes could endure long into the future. After all, Zoom is now a household name thanks to millions of companies transitioning to remote work and embracing virtual collaboration. The workplace will continue to evolve as organizations look to work smarter and be more efficient. But what is digital transformation? What should organizations be aware of as they continue to move towards the future of work? And how can you overcome the biggest digital transformation challenges to reach success in this new environment?

What is digital transformation?

Digital transformation is different at every organization. It involves having an open mindset to establish new paradigms with how teams work internally with each other and externally with customers. It’s about leveraging modern technology to inform how a business is run and encompasses everything from improving business processes, to revamping your internal culture, and enhancing customer interactions.

With the massive shift to digital, the increase of emerging tech has led many companies to experience digital fatigue as they adopt more apps and software to “always be on” while working remotely. It’s not just about adopting technology, though. It’s also about having a forward-thinking growth mindset. On the corporate side, being able to innovate faster and keep up with the times are at the top of the priority list of why organizations embrace digital transformation.

5 Digital Transformation Challenges and How to Beat Them | Wrike

There are many reasons why you might consider investing in technology, but successfully implementing it often comes with the following digital transformation challenges.

Five common digital transformation challenges

Establishing executive buy-in

Getting executive buy-in is often the biggest hurdle because they may have established workflows or invested in tech that were once effective but are now outdated. The pandemic may have changed all that.

At the beginning of 2020, 67% of U.S. CEOs expressed concerns about migrating all of their business to the cloud. At present, most companies have had no choice but to embrace digital technologies. That initial hesitation quickly switched to necessity — so much so that 70% of CEOs say that the creation of new digital business models and revenue streams has been accelerated by months or years due to the pandemic.

5 Digital Transformation Challenges and How to Beat Them | Wrike


Hard to argue with results like that. To keep up with the times, not giving new technology or processes a chance can be even riskier than doing nothing.

Dealing with employee pushback

On the flip side, your executive management team may be now challenging the status quo they established when the company was founded and going all-in on digital transformation. Just because the C-level may be convinced that disrupting business processes and investing in newer digital tools is the new way to go, doesn’t mean everyone in the organization has bought in. So, if getting executive buy-in is priority one — since they approve the budget — then getting departmental buy-in from team leaders and their employees is priority one-A. They’re likely the ones using these tools on a daily basis so they need to buy-in more than anyone.

With any new tech on the job, your team might be uncomfortable using it at first. That’s normal because they’re accustomed to familiar processes and by introducing anything new, that familiarity is disrupted. “That’s the way we’ve always done it” can’t be a valid response when an organization looks to outpace its competition and scale. Just make sure the reasons for embracing digital transformation are for the long term. Remember, your digital transformation journey doesn’t belong to one individual or department.

Keep employees engaged during the onboarding process by encouraging them to ask questions and be involved with the deployment. Doing this can empower them and have them feel more involved in the decision making rather than being mandated to use the new tech. Furthermore, already having (or implementing) an agile strategy can help your team navigate uncertainty as you roll out new technologies or processes during the Next Normal.

You’re relying on legacy tools too much

Imagine if your team was limited to pen and paper; using sticky notes to communicate, desk calendars to schedule meetings, and relying on phone calls to check in on projects. It’s hard to fathom any business in 2021 being able to scale and collaborate efficiently with such primitive methods when there’s many sophisticated solutions now available. 

If you’re relying on legacy tools like email and spreadsheets, which are no doubt a step above handwritten notes and phone calls, these have their own set of limitations. Your inbox and spreadsheets still have a place, but modern teams need more than these foundational tools.

The biggest issues are scalability and versatility. Searching your email for project updates and asset feedback is tedious and time-consuming. Questions like, “Where is the most recent version of the demo video?” and “Which one-pager do I need to give feedback and approve?” would be difficult to resolve scouring your email inbox. 

With spreadsheets, not only are they mind-numbing to look at, but even with advanced formulas and formatting, they lack the versatility of cloud tools. And you can forget about saving files to spreadsheets or setting project reminders because that’s nonexistent with Microsoft Excel or Google Sheets. Features like online visual asset proofing provide widespread visibility into time-sensitive feedback along with automatic user notifications, which speed up approval times. 

Collaborating is easier than ever today because everything lives in the cloud. When you manage your work in a collaborative work management (CWM) solution like Wrike, it’s a master system of record that stores all your comments and file updates, automates approvals, tracks your team’s hourly rates, and a whole lot more. Plus, with built-in features like the @mention and cross-tagging, you can keep everyone in the loop. It’s your paper trail that details everything happening with ongoing and future work.

5 Digital Transformation Challenges and How to Beat Them | Wrike

When an organization’s goal is to be agile and scalable, relying on legacy tools might be “familiar” but not the best business decision. Updating your tech stack would be best for the long term, even if there are short-term struggles with getting your team onboard.

Overcoming budget constraints 

Adopting a digital transformation mindset is necessary to innovate faster and be more resilient, but your budget may be limited to move away from legacy processes into more modern tools. Building the business case for a new technology can be intimidating because it’s often seen as your “one shot” to get budget approval.

When it’s time to introduce a new technology to your team, it’s easier when there are low barriers to entry, like a software free trial. As you begin building the business case, give examples of how your team missed a deadline or is constantly experiencing bottlenecks with its work and not meeting its KPIs. Then, experiment by managing a few projects in a new software and document your team’s experience. What was superior compared to the old system? Could they track project progress better? What were the bottom-line results? Analyzing the project and answering these types of questions can go a long way in getting budget approval.

Wrike Free, for instance, allows unlimited users to manage their work in a centralized hub, typical of how enterprise and hypergrowth organizations manage their work. Unlimited users means nobody on your team is excluded and gets to work out of the same platform. With 200 subtasks available, it’s a fantastic entry point for organizations looking to experience the benefits of a robust CWM system.

Syncing all your tech

As you consider adding new tools to your tech stack, figuring out how to make them pass the relevant data back and forth can be overwhelming. Unless you have a strong IT or technological background, dealing with APIs can be confusing and too much “tech speak.” 

When you work in Wrike, integration is a breeze because Wrike Integrate enables you to sync more than 400+ prebuilt connectors to cloud and on-premises enterprise applications. It also lets you connect Wrike to thousands more using universal connectors to apps with accessible APIs. What’s even better, it’s a no-code system, and very intuitive for any user skill set.

5 Digital Transformation Challenges and How to Beat Them | Wrike


Don’t let digital transformation challenges overwhelm you

Whether you’re looking to adopt new technologies or revamp your business processes, don’t let it overwhelm you. When you’re ready to experience how hypergrowth and enterprise organizations manage their work with a CWM, go here to start your Wrike free trial.

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