1. Strategic Challenges
2. Technical Barriers
3. Organisational Challenges
4. Automation: Your Shortcut to Overcoming Digital Transformation Challenges
5. The Cloud
6. Spotlight on Google Cloud
7. The Path Forward

84% of companies fail at digital transformation.

By now, businesses understand the importance of digital transformation. When done right, it goes beyond modernising operations to reshape your business - faster, more competitive, and primed for new opportunities.

But let’s face it: the path to transformation isn’t always smooth. The challenges can feel overwhelming, and it’s easy to get stuck.

The good news? By using technology, and adopting some proven strategies, these barriers dissolve. I’ll describe the most common barriers to Digital Transformation - and how to overcome them.

Strategic Challenges

Leadership and Vision

Without a clear vision, digital transformation can quickly veer off course. Teams end up pulling in different directions, and valuable time and resources slip through the cracks.

Strong leadership is the antidote. A clear, shared vision gives teams a direction to follow. Here’s how business leaders can keep things on track:

1. Define your goals: Outline what success looks like for your business. Keep it specific, measurable, and achievable.
2. Set the pace: Break transformation into smaller, actionable milestones. These “quick wins” keep momentum high and teams motivated.
3. Unite your teams: Foster collaboration by ensuring everyone understands their role in the bigger picture. Tools like shared project dashboards can simplify communication.

The leadership team needs to choose the right approach and get everyone motivated around that common goal. A digital transformation framework can provide that structure - we’ve got a full article that’ll help you here.

Budget Constraints

Financial limitations can feel like a dealbreaker for digital transformation. It’s no surprise—most IT budgets are eaten up by maintaining legacy systems, leaving only 19% for new technology. That leaves businesses stuck, with 34% calling a lack of resources their biggest roadblock.

Here’s the good news: budget doesn’t have to hold you back anymore. All businesses have processes that are outdated, usually manual, and a drain for time and money. Nearly all repetitive tasks of this kind can be automated in some way - which is an immediate saving.

If you have Microsoft 365, tools like Copilot Studio allow you to build tailored automations that fit your business perfectly - with a cost similar to a regular Microsoft 365 licence. It’s efficient, scalable, and far more accessible than you might think.

Elsewhere, it’s pretty likely that you’re using SaaS tools. The more tools, the more they cost. Bespoke software can be a great way to achieve your unique goals without relying on multiple SaaS platforms (and the cost of getting them to play well together).

Regardless of your approach, by investing in systems that do exactly what you need, you’ll cut out unnecessary costs and free your business from the limitations of one-size-fits-all tools.

Digital transformation isn’t about spending more - it’s about spending smarter.

Technical Barriers

Legacy Systems

Outdated infrastructure doesn’t just slow progress for businesses. It actively creates bottlenecks, blocking modern tools from working effectively and turning digital transformation into an uphill battle.

The reality: innovation doesn’t have to wait for a full upgrade. Start by identifying the ‘most broken’ aspects of your workflow. Particularly where it aligns with your goals or values. If customer service is your focus, begin by upgrading systems that empower your customer service. If legacy systems have security issues, they become more urgent, so should be prioritised.

Instead of ripping out everything at once, start by integrating tools that bridge the gap. Platforms like Microsoft 365 can layer over legacy systems, bringing automation, efficiency, and innovation without a full-scale overhaul.

For businesses ready to take it further, cloud-based solutions can replace clunky infrastructure bit by bit. This phased approach means you modernise at your pace, without breaking the bank or disrupting daily operations. (I talk about this Staged Approach to Digital Transformation more here).

Cyber Security

Cyber security risks cast a long shadow over digital transformation. The fear of breaches, data theft, or operational disruption is real - and it’s enough to slow decision-making to a crawl. It’s no surprise that 40% of CEOs rank cyber security as their top concern.

Strong cyber security enables digital transformation. By taking a proactive approach, you can move forward confidently:

• Modern platforms have security built in: Tools like Google Cloud come with enterprise-grade protections as standard, helping you stay secure as you grow.
• Automate threat detection and response: Identifying risks and reacting in real-time, reduces the pressure on your teams and ensures nothing slips through the cracks.
• Stay one step ahead with zero-trust architecture: By verifying every user and device, you limit exposure and keep critical systems locked down.

When cyber security is part of the plan - not an afterthought - it becomes a foundation for you to build technology into your operations. It gives you the confidence to transform at speed without compromising safety.

Organisational Challenges

Skills Gap

Digital transformation is only as strong as the people driving it. But finding the right talent isn’t easy - 54% of organisations struggle to hit their goals due to shortages in critical areas like cyber security, data analytics, and software integration. Without the right expertise, projects stall, teams get frustrated, and progress grinds to a halt.

Here’s how to bridge the gap:

1. Leverage upskilling and reskilling: Invest in your existing teams. Platforms like Microsoft Learn and LinkedIn Learning offer accessible, targeted training to boost skills in key areas without long-term disruption.
2. Partner with external experts: Outsourcing to specialised providers can inject the skills you need, exactly when you need them. Whether it’s automating workflows, integrating new tools, or bolstering cyber security, a reliable partner keeps your plans on track.
3. Embrace low-code tools: Platforms like Power Automate and Copilot Studio allow teams to build workflows and automations without needing deep technical expertise. It’s an efficient, accessible way to drive transformation.

A skills gap doesn’t have to mean stalled progress. With the right mix of training, tools, and partnerships, you can equip your teams to succeed and keep your transformation moving forward.

Cultural Resistance

Change is hard—especially when it disrupts familiar ways of working. Moving from traditional workflows to tech-driven processes can spark pushback when teams feel left out, poorly supported, or blindsided by change. Without clear communication and proper training, frustration and resistance are almost inevitable.

To overcome this, communicate early and clearly, showing your teams why the change matters and how it will make their day-to-day roles easier. Involve them in the process from the beginning. When employees have a voice in shaping how new tools are adopted, they’re far more likely to feel ownership and support the transition.

Make sure to also equip people with the skills and confidence they need to use any new systems effectively. And don’t underestimate the value of celebrating progress. When small wins are highlighted - whether it’s a streamlined workflow or saved hours - it proves that the change works, building trust and momentum along the way.

Above all, lead by example. If you’re happy to put up with inefficient processes, that stance will be reflected through your organisation. As a start, read our guide: 5 Things Any Business can Automate in 2025.

Automation: Your Shortcut to Overcoming Digital Transformation Challenges

How much time do your teams lose to repetitive, manual tasks every week? Over a year, those lost hours add up to wasted productivity—and missed opportunities. It’s no surprise that 98% of executives see AI and automation as critical to their future strategies.

By streamlining processes and reducing manual workloads, automation helps businesses operate more efficiently, scale effectively, and free up teams for higher-value work.

In practice, automation replaces repetitive tasks with systems that work around the clock. Intelligent systems deliver consistent, accurate results, minimising errors and protecting customer trust. And because automation scales seamlessly, businesses can grow without a surge in resources or costs.

Take accounts payable as an example: traditionally time-consuming, automation handles invoice matching, approvals, and payments with minimal oversight, leaving finance teams free to focus on strategy.

The benefits speak for themselves:

• Efficiency: Automate repetitive tasks, freeing employees for strategic work.
• Cost Savings: Minimise errors and resource waste.
• Enhanced Security: Automate compliance checks and security protocols.
• Collaboration: Improve visibility and data sharing across teams.

The Cloud

Feature	Legacy Systems	Cloud-Based Solutions
Scalability	Fixed capacity, requires expensive hardware upgrades.	Highly scalable, adjusts to demand with minimal downtime or cost.
Cost	High upfront costs for hardware and ongoing maintenance expenses.	Pay-as-you-go pricing model with lower initial investment.
Integration	Limited compatibility with modern tools and technologies.	Seamless integration with AI, ML, analytics, and other advanced tools.
Accessibility	On-premises access, with limited remote capabilities.	Accessible from anywhere with an internet connection.
Security	Relies on outdated protocols and is vulnerable to breaches.	Advanced, built-in security features like encryption, IAM, and compliance tools.
Maintenance	Requires dedicated IT teams for updates, patches, and troubleshooting.	Managed by the cloud provider, with automated updates and minimal maintenance effort.
Data Management	Creates silos, making it difficult to share and analyse data efficiently.	Centralised data storage, allowing for real-time analytics and easy sharing.

Spotlight on Google Cloud

Google Cloud provides a robust toolkit for tackling digital transformation challenges head-on. Here’s how it can help:

Scalability and Flexibility

Whether you’re a fast-growing startup or an established enterprise, Google Cloud scales effortlessly to meet your needs. It adapts to changing workloads without costly hardware upgrades, so you can focus on growth without worrying about infrastructure keeping up.

Built-In Security You Can Trust

Security is baked into Google Cloud. With features like Identity and Access Management (IAM) and advanced encryption, Google Cloud protects your data from every angle. It also helps you meet industry compliance standards, so you can stay confident and secure in an ever-changing threat landscape.

Collaboration That Works Anywhere

Google Workspace tools - like Docs, Drive, and Meet - integrate seamlessly with Google Cloud, enabling real-time collaboration from anywhere. Whether your teams are in the office, remote, or hybrid, everyone can work together on shared files without missing a beat. For small businesses, tools like Docs, Sheets, and Slides are an added bonus - they’re free and come packed with the functionality most teams need.

Insights That Drive Better Decisions

Data is powerful, but only if you know how to use it. Google Cloud’s analytics tools, like BigQuery, turn your data into real-time, actionable insights. By centralising and analysing your information, you can make faster, smarter decisions that drive your business forward.

With Google Cloud, digital transformation doesn’t have to be overwhelming. It delivers smart infrastructure, strong security, and tools that empower your teams to work better, wherever they are.

The Path Forward

Successful digital transformation projects don’t just focus on upgrading technology; IT is important, but creating sustainable change in your business means aligning your team and operations with a clear, unified vision.

Success lies in planning, persistence, and a willingness to evolve. For businesses looking to transform, the rewards - greater efficiency, innovation, and growth - are well worth the effort.

Ready to take the leap? Contact us today for tailored automation solutions that drive your transformation forward. Let’s build the future, together.

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