How to Close Your IT Talent Gap With Automation and Upskilling The ongoing IT talent shortage continues to place growing pressure on organizations to keep up with rising workloads and evolving technology demands, and hiring alone is no longer enough. In this video, we'll outline a 90-day program that helps IT leaders and MSPs close the talent gap through automation and structured upskilling. Before we begin, be sure to subscribe to NinjaOne's IT video hub and our YouTube channel for more tech content like this. Days 0–30: Measure, Triage, and Create Time In the first 30 days, the focus is on assessing your current workload, identifying automation opportunities, and creating dedicated time for learning, laying the groundwork for measurable improvements. Capacity Assessment Before making any changes, start by getting a clear picture of your team's workload. Track key metrics like tickets per technician, devices managed, and recurring task categories. Then, identify three to five repetitive, low-risk tasks that are strong candidates for automation, such as restarting services or clearing disk space. Skill Mapping Once you have your operational data, assess your team's skills and identify the gaps. Build a competency matrix that outlines the required skills for each role. This could include technical, procedural, and soft skills. Then, rate each team member's current proficiency. Pair developing technicians with mentors who are strong in the one or two target competencies each technician is working to develop. By day 30, your team should have a documented operational baseline, two to three automations in production, standardized SOPs, and active mentor- mentee pairs driving focused skill development. Days 31–60: Stand Up Learning Paths and Shift Left In days 31 to 60, the focus shifts to building on your foundation by formalizing learning paths, empowering frontline technicians to take on more complex work, and expanding your automation efforts. Learning Paths Create structured learning paths that guide each team member from novice to independent contributor, and include practical capstone tasks that demonstrate proficiency before moving to the next stage. Define clear progression stages for each role: learn, shadow, perform with supervision, then perform independently. Shift-left Practices Use detailed playbooks, SOPs, and guardrails to make advanced tasks approachable, consistent, and safe to execute. Add peer reviews for technicians' first few solo executions to reinforce quality and knowledge sharing. By day 60, your team should have live learning paths, 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 Competency Validation The final phase is about locking in your progress with measurable gains already in place, the focus now shifts to formal validation, clearer career paths, and targeted hiring to fill only the skill gaps that remain. Sustaining Progress Beyond the 90 Days Sustaining momentum beyond the initial 90 days requires consistent supporting practices that keep growth ongoing, results visible, and improvements aligned with business goals. Closing the IT talent gap is an ongoing effort, not a one-time fix. By following this framework, IT leaders can build teams that continuously improve and deliver stronger service outcomes. For more information, check out our official blog post on closing the IT talent gap with automation and upskilling, linked in the description below.