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How to Close Your IT Talent Gap With Automation and Upskilling

by Jarod Habana, IT Technical Writer
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Key Points

  • Follow an IT upskilling plan: Implement a 90-day IT talent gap program that combines automation, mentorship, and role-targeted upskilling.
  • Automate IT tasks: Automate repetitive operational tasks to reduce technician workload and reallocate time to higher-value learning and strategic work.
  • Use learning paths: Role-based learning paths integrate hands-on practice, mentor support, and measurable skill checks for faster tech capability growth.
  • Shift-left IT strategy: Equip frontline technicians to handle more complex tasks with playbooks and guardrails, for fewer escalations and faster response times.
  • Measure IT performance: Track automation impact, skills progress, and service metrics to demonstrate ROI and sustain improvement.
  • Continuous learning: Beyond 90 days, do recurring reviews, performance scorecards, and ongoing learning for long-term scalability and resilience.

There has been an ongoing IT talent shortage in every industry, challenging organizations to keep up with rising workloads and evolving tech demands. Simply hiring new employees is no longer enough to stay competitive, so IT leaders and managed service providers (MSPs) must focus on closing the tech talent gap by combining automation with deliberate upskilling.

Keep reading to learn how to create a 90-day program that accelerates proficiency and retention while handling more work more consistently.

Create a 90-day program to reduce the tech skills gap

A structured approach is crucial when building a 90-day program to close the IT talent gap. You need a repeatable system if you aim to balance measurement, automation, and skills development, while expanding your team’s capacity and improving day-to-day efficiency.

📌 Prerequisites:

  • Baseline metrics for volume, backlog, service levels, and after-hours load
  • Skills inventory that lists required competencies per role and current team proficiency
  • Defined mentors and time allocation for coaching and practice
  • A shortlist of high-frequency tasks that are eligible for automation
  • Role scorecards for near-term hiring

Days 0–30: Measure, triage, and create time

For the first 30 days, the program should focus on understanding the current workload, identifying automation opportunities, and carving out time for learning. This phase will set the foundation for measurable improvements.

Capacity assessment

Before making changes, you need a clear picture of the team’s actual workload and constraints.

  • Quantify the work: Track tickets per technician, devices managed per person, change requests, and recurring task categories.
  • Find toil candidates: Select three to five repetitive, low-risk daily tasks (e.g., restarting services, clearing disk space) that could be safely automated within the next month.

Skill mapping

After collecting operational data, map out your team’s competencies and gaps.

  • Build a role competency matrix: For each role, list the required skills (technical, procedural, and soft skills) and rate each team member’s current proficiency.
  • Assign mentors strategically: Pair each developing technician with a mentor who is strong in their target skills, ensuring every mentee has one or two focused competencies to work toward.

Quick wins

Quick wins help build momentum and confidence across the team.

  • Standardize SOPs: Document and publish step-by-step procedures for your most repetitive workflows.
  • Launch one automation per week: Roll out small, safe automations that immediately reduce queue volume (e.g., alert acknowledgment).
  • Protect learning time: Block dedicated time each week for team members to shadow mentors, complete training modules, or practice new skills.

By the end of the first 30 days, your team should have a documented operational baseline, two to three automations in production, standardized SOPs for key workflows, and active mentor-mentee pairs driving focused skill development.

Days 31–60: Stand up learning paths and shift left

The second phase should build on what you established during the first 30 days. You must now formalize development through learning paths, pushing work closer to the front line, and expanding automation.

Learning paths

Establish structured learning paths that guide each role from novice to independent contributor.

  • Define the sequence for each role: Outline clear stages (learn, shadow, perform with supervision, and perform solo), so progress is visible and consistent.
  • Add capstone tasks: Include small, practical projects or deliverables at the end of each stage to confirm both proficiency and confidence.

Shift-left practices

Empower frontline (L1) technicians to take on more complex tasks previously reserved for higher tiers.

  • Move common L2 work to L1: Use detailed playbooks, SOPs, and built-in guardrails so advanced tasks are approachable, consistent, and safe to execute.
  • Implement peer review: To reinforce quality control and knowledge sharing, require peer validation for the first few solo executions of new tasks.
  • Track impact: Measure the reduction in escalations and monitor any changes in resolution time or service quality.

Automation growth

Keep scaling automation to target higher-value gains.

  • Identify the next three targets: Focus on tasks that frequently interrupt technicians or generate repetitive manual effort.
  • Define measurable outcomes: Each new automation should directly contribute to a key improvement (e.g., fewer escalations, faster resolution, reduced after-hours load).

By the end of Day 60, the team should have live learning paths for key roles, more work being resolved at the frontline level, and a measurable reduction in escalations and manual interventions.

Days 61–90: Certify, scale, and hire into clarity

The last phase should focus on formal validation, organizational structure, and precise hiring. By then, the team should have built momentum with measurable progress, and the goal is to lock in those gains through certification, clear career paths, and strategic recruitment that fills only the remaining skill gaps.

Competency validation

Use structured assessments to turn learning progress into proven capability.

  • Run practical evaluations: Do short, scenario-based tests or live exercises that align directly with each learning path.
  • Promote based on performance: Recognize advancement through demonstrated outcomes, not just completion of training materials.

Organizational clarity

Motivate ongoing growth by providing transparency and structure.

  • Publish role ladders: Define clear levels for each technical role with associated competencies and responsibilities.
  • Set promotion criteria: Make advancement criteria objective and consistent across the team.
  • Enable mobility: Open lateral or vertical moves for team members who demonstrate readiness to encourage retention through opportunity.

Targeted hiring

Fill the remaining capability gaps based on measurable data.

  • Use role scorecards: Align hiring profiles directly with the skill shortages not yet addressed by upskilling.
  • Pilot apprenticeship programs: Bring in early-career talent through structured internships or apprenticeships to shorten ramp time.

By the end of Day 90, the team should have certified competencies, transparent career ladders, and targeted hiring efforts precisely aligned to fill unmet needs.

Sustaining progress beyond the 90 days

The framework must help to keep your momentum and drive lasting impact after the initial 90 days. These supporting practices help keep growth continuous, results visible, and improvements aligned with business goals.

Mentorship that works in busy teams

Effective mentorship doesn’t always require long sessions. Instead, it thrives on structure, consistency, and real work. You want to keep the process lightweight and focused to help even busy teams develop talent without losing productivity.

  • Hold short, weekly meetings: Keep sessions under 30 minutes with clear goals.
  • Practice on live work: Use real tasks with checklists and rollback plans to ensure safety and relevance.
  • Track progress: Maintain a simple, visible dashboard showing skills attempted, approved, and next steps.

Automation that actually sticks

For automation to deliver lasting value, it needs to be intentional, well-documented, and reviewed on a regular schedule. Focus on impact, safety, and sustainability, not just on volume.

  • Select the right tasks: Automate high-volume, repetitive jobs with clear inputs, predictable outcomes, and low failure risks.
  • Document thoroughly: Capture preconditions, error handling, and rollback steps so automations remain reliable as the environment evolves.
  • Review monthly: Evaluate performance, retire automations that no longer provide ROI, and refine those with improvement potential.

Metrics and reporting

Make progress visible and actionable with a concise, recurring scorecard that ties automation and upskilling to service outcomes.

  • Capacity and outcomes: Track tickets per tech, time to first response, time to resolve, and escalation rate.
  • Automation impact: Monitor automation coverage by category and hours saved per month.
  • Talent and learning: Measure path completion, signed-off skills, internal promotions, and new-hire ramp time.
  • Cadence: Share a one-page scorecard every 30 days that highlights key improvements and next priorities.

NinjaOne integration

NinjaOne’s platform can provide automation, visibility, and reporting capabilities to execute and sustain this 90-day program effectively.

CapabilityHow it helpsKey benefit
Automation at scalePackage and schedule routine remediation, patching, and checks to reduce queue volume and manual effort.Frees technician time for higher-value work and learning.
Onboarding playbooksDeploy role-based scripts, tools, and policies to ensure new hires are productive from day one.Accelerates ramp-up and consistency across roles.
Operational visibilityExport device counts, ticket metrics, and automation runs to quantify time saved.Enables data-driven decisions and capacity planning.
ReportingGenerate 30-day scorecards showing automation coverage and service improvements by client or team.Maintains transparency and momentum through regular reporting.

A systematic path to IT capacity and retention

Closing the IT talent gap should be an ongoing system of measurement, automation, and growth. With the steps outlined in this article, IT leaders can create teams that continuously improve while delivering stronger service outcomes. Just make sure to focus on building a culture where people and technology can scale together to ensure success.

Related topics:

FAQs

The tech skills gap refers to the growing difference between the skills organizations need to operate effectively and the abilities their current workforce possesses. It’s driven by rapid technology change, shifting business needs, and a shortage of qualified professionals.

Create time by automating two or three high-volume tasks first. Protect one hour per week for mentorship and pair it with live work so learning happens naturally within existing workflows. This keeps development continuous without adding extra burden.

Choose repeatable tasks with high frequency, low risk, and clear rollback procedures. Measure their impact by tracking queue reduction and total hours saved per month.

Attach each module to a real task, add a small capstone project, and require mentor sign-off to mark completion. Review progress during weekly standups to keep accountability high. This consistent rhythm prevents momentum from fading.

Hire when a skill is mission-critical, can’t be developed internally within one or two quarters, or poses a significant operational risk if left unfilled. Upskilling should handle the rest to preserve continuity and culture.

Track automation hours saved, improvements in time to resolve, and completion rates for learning paths. Share a one-page monthly summary showing measurable gains in efficiency and internal promotions. This helps demonstrate ROI to both leadership and staff.

Start with a single focus area, such as ticket automation or L1 skill growth. Once that foundation delivers visible results, expand to additional roles and workflows.

Keep the same rhythm (measure, automate, learn, and report) on a quarterly cycle. Regular reviews and updated scorecards ensure continued growth and long-term success.

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