In this article, we explore the challenges businesses face during digital transformation, as shared by seventeen industry professionals including CEOs and Digital Transformation Consultants. Their insights range from the initial hurdle of alignment across projects to the final challenge of tackling resource scarcity. Dive into their experiences to better understand and navigate your own digital transformation journey. When it comes to mastering digital transformation, what are the key challenges?

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  • Alignment Across Projects
  • Securing Employee Buy-In
  • Adapting Growth Strategies
  • Navigating Remote Software Integration
  • Bridging the Generational Digital Divide
  • Aligning Tech Investments with Goals
  • Overcoming Resistance to Change
  • Prioritizing Transformation Areas
  • Addressing Lack of Understanding
  • Managing Unexpected Responsibilities
  • Differentiating Transition from Transformation
  • Solving System Overload Issues
  • Managing Funding and Budget Constraints
  • Improving Marketing Attribution
  • Ensuring System Interoperability
  • Addressing Cybersecurity Vulnerabilities
  • Tackling Resource Scarcity

Alignment Across Projects 

Without a doubt, the biggest challenges are strategic alignment and adoption across the organization, but also across projects. You have to have a full view of all projects going on in silos that can be counter to the success of your initiative. Long-term adoption and accountability for achieving business objectives is critical to maximizing transformation ROI.

Julie Rinard, Digital Transformation Consultant

Securing Employee Buy-In

One significant challenge in digital transformation is managing organizational change and securing employee buy-in. The transformation is not merely a technological shift, but a comprehensive alteration in operations, culture, and workflows, which can lead to employee apprehension.

Addressing this requires clear communication and ample training. Employees need to understand the “why” behind the changes and how they align with the organization’s goals. Importantly, employees should be turned into advocates of change, not opposition. It is crucial to ensure they are on the same page and comprehend the entire process.

Fostering a culture of innovation, flexibility, and adaptability is also essential. By focusing on the human element, addressing concerns with empathy and support, and turning employees into advocates for change, businesses can successfully navigate the complexities of digital transformation and pave the way for a prosperous digital future.

Oleh Sorokopud, Head of Digital Marketing, Softjourn

Adapting Growth Strategies

Adapting the company’s strategy for growth was definitely the most challenging for me. Each level of your business needs change. For example, there’s no question that digital marketing is more effective and cheaper, but figuring out what tools to use and their effectiveness took weeks upon weeks of studying. 

That doesn’t just go for me as an owner; it goes for all my employees too. You’ll be lucky if your entire workforce can transition to the new business model. Chances are, some employees who were good before may be costing you money now. You’ll either have to train them extensively or rehire altogether. 

All of this is going to be part of your change-management strategy. Yes, you need a proper strategy before you begin the transition. It’ll be disastrous if you go into digitizing without the proper steps, and those steps need to be gradual and deliberate. If you go into it blind, it’ll be extremely frustrating for your team members and your customers.

Khunshan Ahmad, CEO, InsideTechWorld

Navigating Remote Software Integration

One key challenge in digital transformation is effectively integrating new software while navigating the complexities of remote work. As an IT consulting firm CEO, I’ve seen that remote settings complicate software rollouts. Traditional in-person training and support are harder to execute, and gauging team adaptation becomes a challenge.

The solution lies in robust change-management strategies, including comprehensive remote training and continuous support. In a remote work environment, thoughtful planning is crucial to ensure that new software enhances, rather than disrupts, business operations.

Søren Rosenmeier, Senior Partner and Group CEO, Right People Group

Bridging the Generational Digital Divide

One of the key challenges often arises from the digital divide – particularly between Gen Z and millennial employees and older generations like boomers and Gen X. Though the latter have been with the company for a long time and usually hold more senior positions, they might not have fully integrated themselves into the process of digital transformation.

Since they have developed their own methods and processes over the years, if not decades, they may prefer to stick with what they know and have been doing. For instance, they may favor traditional face-to-face meetings over virtual ones or prefer traditional sales and lead-generation methods and not take advantage of digital marketing and AI tools. Bridging this “digital divide” is crucial to the digital transformation process.

Mark Chang, Founder and Head of Design, Intenza Fitness

Aligning Tech Investments with Goals

In my experience, one of the biggest challenges faced by businesses in a period of digital transformation is change management. This involves aligning tech investments with strategic goals, integrating legacy systems, and empowering employees with digital skills.

From a digital marketing perspective, it’s clear that many businesses, especially smaller ones, face challenges in embracing the digital age. A common stumbling block is the hesitation to dive into digital campaigns due to a lack of knowledge in areas such as website development and SEO. Reluctance to change traditional practices is widespread across various industries.

However, it’s important to understand that neglecting online marketing efforts can hinder a business’s online visibility, engagement with customers, and overall growth.

To ease change anxiety, businesses should begin by defining their goals. Establishing clear objectives serves as the bedrock for a successful change management strategy.

Jordan Bridge, Digital Marketing Executive and Cyber Security Officer, Growthlabs

Overcoming Resistance to Change

The biggest challenge I’ve seen is resistance to change.

When we first introduced new digital tools like VR walkthroughs and real-time renderings, some designers clung to traditional, static methods. Change is uncomfortable.

However, embracing emerging technologies has allowed us to visualize spaces with far more speed, personalization, and interactivity. After seeing the benefits firsthand, even hesitant creatives got on board.

For instance, one architect was convinced VR would undermine his finely-tuned design sensibilities. But once he could dynamically showcase homes to clients in virtual reality, he became a total evangelist.

Now, our entire design process is digitized, from collaborative sketching apps to automated rendering. It has accelerated our workflows exponentially while unlocking new creative possibilities.

True digital transformation requires an openness to entirely new ways of working. With the right cultural nudge and change management, skeptics can become champions.

Lukas Berezowiec, Founder CEO, NoTriangle Studio

Prioritizing Transformation Areas

Our business has always been on the digital forefront, but there are still processes we need to upgrade to improve our systems. The most underrated challenge of digital transformation is deciding which areas of your business will benefit the most from the transformation. 

It’s less about getting to everything eventually, but more about which areas will drive the most revenue for the business. Usually, this would mean looking at improving the product or marketing efforts. 

But we found that it wasn’t that simple just to improve those areas. With the advent of AI, we needed to do a quantitative analysis of administration, HR, and customer experience to get a better picture. 

This was a massive undertaking, but once we got a detailed lay of the land, we could move on to the next challenge of choosing the right digital tool to transform our customer experience. We settled on an AI platform that helps us automate customer query responses and suggest relevant products to them.

Alister Wood, Owner, VisitUs

Addressing Lack of Understanding

One of the biggest challenges I see businesses face when trying to transform their organization is a lack of understanding.

For example, many companies have some kind of digital initiative already in place but haven’t yet realized that they need to change the way they do things. They’re still working with old processes and tools, but with a new layer of technology on top of it. That’s all well and good, but it won’t help you scale or become more agile.

The other challenge is that many businesses are trying to do this on their own—they don’t want to bring in an outside consultant or team member who could help them make sense of what they need, who could help them understand what is possible, and who could make sure they’re putting together a long-term strategy that works for their company’s unique needs.

Jaanus Põder, Founder and CEO, Envoice

Managing Unexpected Responsibilities

Digital transformation will teach you just how often responsibilities land on a person or team, rather than being placed there by a team leader. This usually happens naturally over time, but with a digital transformation, nothing is yet set in stone. You may find that HR ends up in charge of unexpected parts of an IT process—it happens! Proper planning can help tremendously here, but you know what they say about the best-laid plans. You really can’t prepare for the unexpected, at least not entirely.

Mark Varnas, Principal SQL Server DBA and Consultant, Red9

Differentiating Transition from Transformation

Transformation or transition? One of the biggest challenges with digital transformation is that the business’s leadership doesn’t always understand what it means. Making offline processes “digital” isn’t transformation; it’s digital transition. Transformation is about leveraging digital to reimagine the organization, processes, services, and practices. It’s about taking the opportunity to innovate, to differentiate, and to optimize beyond the small gains available from digital transition. This is a particular challenge for mature businesses. They can spend years on big, so-called “digital transformation” projects, only to find that they have made minor gains. Meanwhile, their challenger competitors have disrupted the market with genuine digital transformation.

Paul Blunden, Founder and CEO, UX247 Ltd

Solving System Overload Issues

In every wave of technological development, most organizations adopt cutting-edge technologies. Each department may use different systems for analytics, project management, prototyping, and other digital tools. However, this causes significant complications — various systems are layered on top of each other, reducing employee productivity.

Switching from one system to another to fulfill individual business functions overloads people in the company. In addition, the digitalization of business requires a training course for employees, which can be quite expensive. Also, staff often have a negative attitude towards innovations, and it takes time to get used to them. All of these factors slow down business processes.

Alexander Kuznetsov, Digital Reputation Expert, RCheckUP

Managing Funding and Budget Constraints

One of the prominent challenges businesses face in this digital world is managing funding and budget constraints. Many business leaders often miscalculate the financial requirements necessary for crafting modern software. As the intricacies of such software evolve and wages ascend, securing adequate funds becomes daunting for numerous companies.

It’s all too common to allocate significant resources towards the latest digital tools without discerning their tangible business value. The golden rule is to focus on a select few initiatives with quantifiable business outcomes. Firms with well-articulated digital goals consistently outpace their counterparts, but it’s also essential to scrutinize whether transformation endeavors are not only achievable but also fruitful. Many organizations introduce features based on unvalidated assumptions, when it should be about launching solutions and fine-tuning based on genuine user and client feedback.

Lorenzo Nourchan, CEO, Northstar Financial Consulting Group

Improving Marketing Attribution

Nearly all businesses face a gigantic challenge when it comes to attribution because marketing initiatives seem to be all over the place. The median small business owner/marketer thinks a bit like this:

“Set up a Facebook page and run ads on social?” Sure, why not.

“Run some Google Ads?” Sounds like a plan. Everyone else is trying it.

“Write a ton of random blog articles so that you can pray that it will help you rank?” Why not? Let’s try it. ChatGPT can do this for us.

But you see, whenever your marketing has become a “let’s try something new” type of strategy, you are probably doing a disservice to your budget, and your business’ roadmap, by not ensuring that your marketing efforts are being correctly tracked or attributed.

If you’ve been in business for more than a year, and have at least broken even, you should already have more than 75% of the info you’ll ever need to know what marketing initiatives you should keep or stop doing.

Jorge Alberto Fuentes Zapata, Founder, Fuentes Zapata Co.

Ensuring System Interoperability

Interoperability of systems was our biggest challenge with our company’s digital transformation. It’s one thing to make digital versions of your current business model, and it’s another thing to make everything work together seamlessly. 

It is not enough to just put up a website. You have to ensure that every nook and cranny of your website is functioning properly, from landing pages to inquiries, contacts, payments, etc. Otherwise, you risk turning off your customers because of the poor navigation experience.

Ed Lateef, Founder, Revoltution Labs

Addressing Cybersecurity Vulnerabilities

The increased risk of cybersecurity vulnerabilities is one of the biggest obstacles firms face when undergoing digital transformation. Organizations that adopt new technology become more linked and data-driven, which attracts cyberattacks and makes them attractive targets. It becomes more difficult to maintain the security of digital assets, sensitive consumer data, and intellectual property.

It’s crucial to keep up with emerging cyber threats, keep personnel trained to spot dangers, and maintain strong cybersecurity safeguards. Data breaches, financial losses, reputational harm, and legal repercussions can occur if this challenge is ignored, underlining the urgent need for organizations to prioritize cybersecurity as a key component of their digital transformation plan.

Neal Topf, President, Callzilla

Tackling Resource Scarcity

In my experience, one of the challenges that businesses face during the process of digital transformation is a lack of resources.

The process of digital transformation is inherently complex, and it requires a lot of time and energy to complete. There are many different elements that need to be considered, from the software that needs to be implemented to the hardware that needs to be purchased. And this isn’t even taking into account all the new processes that need to be put in place and training employees on how they should work.

In order for businesses to successfully complete this process, they need to hire more people than usual so that they can handle all these extra responsibilities at once. Having more employees will also help with training them properly so they know what they are doing when they’re working on specific parts of the project (i.e., if someone is designated as responsible for managing IT projects).

Zoltan Fagyal, CEO, Not Just Laptops