Three years ago, I had what I thought was a solid IT team. Strong on infrastructure, reliable on support, capable of keeping the lights on for our e-commerce operation. We had good people doing good work.
Today, that same team composition would leave us dangerously exposed. Not because the people are wrong, but because the skills the business needs have fundamentally changed.
The Ground Has Shifted
Cast your mind back to early 2023. ChatGPT had just launched. Most organisations were still mid-way through cloud migrations. Cybersecurity was important but not yet the board-level obsession it has become.
Now look at where we are:
- AI is embedded in operations. Not as a novelty, but as a core tool. Your team needs to understand AI integration, prompt engineering, data pipelines, and governance frameworks.
- Cloud is the default. On-premises infrastructure has not disappeared, but the centre of gravity has shifted. Your team needs deep cloud-native skills.
- Security is everything. Post-quantum cryptography, zero trust architecture, supply chain security, AI-powered threat detection. The security skills gap has widened enormously.
- Automation has eaten the routine. Ticket routing, user provisioning, monitoring response, patch management. If your team is still doing these manually, you are paying human rates for robot work.
The traditional IT operations role is being compressed from both sides. Automation handles the routine. Specialist skills are needed for the complex work. The middle ground is shrinking fast.
The Roles That Have Changed
The Traditional Sysadmin
Three years ago, we had dedicated system administrators managing on-premises servers. Today, most of that infrastructure runs in the cloud. A sysadmin who cannot write Terraform or navigate Kubernetes is increasingly limited in what they can contribute.
The Helpdesk Technician
First-line support has been transformed by AI-powered service desks, self-service portals, and automated resolution workflows. The role has morphed into something closer to customer experience and technical problem-solving. Soft skills and analytical thinking matter more than knowing how to reset a password in Active Directory.
The Network Engineer
Software-defined networking, cloud-native networking, and zero trust architectures have transformed what it means to manage a network. Traditional knowledge of switches, routers, and VLANs is still valuable, but it is no longer sufficient.
The New Hybrid Roles
What has emerged are hybrid positions that blend disciplines:
- Cloud Security Engineer - combining infrastructure, cloud, and security expertise
- DevOps/Platform Engineer - bridging development and operations with automation
- AI Operations Specialist - managing AI model deployment, monitoring, and governance
- Identity and Access Management Specialist - as zero trust makes identity the new perimeter
- Data Engineer - managing the pipelines that feed both business intelligence and AI
These roles did not exist in most IT departments three years ago. Now they are critical.
The Retraining vs Hiring Dilemma
Do you retrain your existing team or hire new people? The honest answer is both.
The Case for Retraining
Your existing team knows your business. They understand your systems, your culture, your customers. That institutional knowledge cannot be replicated by a new hire. Retraining is also significantly cheaper - the average cost of replacing a technical employee is typically one to two times their annual salary.
The Case for Hiring
Some skills gaps are too wide to bridge through training alone. If you need a senior cloud architect and your most experienced infrastructure person has never worked outside on-premises environments, that is a two to three year development journey.
My Approach: The 70/30 Rule
In our team, I work roughly to a 70/30 split. Seventy per cent of our skills gap is addressed through retraining and upskilling. Thirty per cent requires strategic hiring for critical capability gaps we cannot develop fast enough internally.
Building a Skills Matrix
Before you can close the gap, you need to see it clearly.
Step 1: Define the Skills You Need
Start with your technology strategy, not your current team. For us, that produced five priority areas:
- Cloud-native infrastructure (Azure, AWS, IaC, containers, serverless)
- Cybersecurity (zero trust, threat detection, incident response)
- Automation and DevOps (CI/CD, scripting, platform engineering)
- AI and data (AI integration, data pipelines, ML operations)
- Leadership and communication (vendor management, stakeholder communication)
Step 2: Assess Current Capabilities
Use a four-point scale:
- Awareness - understands the concept but cannot execute
- Developing - can execute with guidance
- Competent - can execute independently
- Expert - can lead others and handle complex scenarios
Involve team members in the assessment. They often have the most accurate view of their own capabilities.
Step 3: Map the Gaps
Plot current capabilities against required. The gaps become immediately visible.
Step 4: Build Individual Development Plans
Align organisational needs with individual motivation. Forcing someone into a role they have no interest in is a recipe for poor outcomes.
The Practical Framework for Upskilling
Dedicated Learning Time
We allocate one half-day per fortnight as protected learning time. No tickets, no meetings, no interruptions. This sounds expensive. It is. But it is cheaper than hiring replacements when your team leaves because their skills are stagnating.
Certification Pathways
We fund relevant certifications for every team member, typically two per year. Current priorities: Azure/AWS cloud, CompTIA Security+ and CySA+, Terraform and Kubernetes, and emerging AI certifications.
Project-Based Learning
The most effective learning happens on real work. I deliberately assign stretch projects that push people into their development areas. This requires accepting that things will take longer. That is the investment.
Mentoring and Knowledge Sharing
We run fortnightly technical sessions where team members present what they have learned. Where we have hired specialists, part of their role is explicitly to mentor and upskill existing team members.
The Human Side
Skills matrices and development plans are the easy part. The hard part is the human element. Some team members will resist change. Some will feel threatened. The key is honest, compassionate communication about where the industry is heading, combined with genuine investment in helping people get there.
The IT skills crisis is real. But it is not insurmountable. The leaders who invest in their teams now will have a significant competitive advantage. Those who ignore it will find themselves constantly hiring, constantly onboarding, and never quite keeping up.
Originally published on danieljamesglover.com
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