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What Tracking Gen AI Skills Can Teach Us About The Future Of Work

To unlock Gen AI's full impact, organizations must measure how employees apply what they learn — from real-time engagement to ROI.

Dr. Gleb TsipurskybyDr. Gleb Tsipursky
October 10, 2025
in Tech
Reading Time: 5 mins read
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What Tracking Gen AI Skills Can Teach Us About The Future Of Work

Generative AI won’t transform your workplace unless you track how well your teams actually use it — from prompt skills to performance metrics that reveal whether learning translates into real-world results.

Generative AI (Gen AI) is reshaping the workplace, offering powerful tools for creativity, productivity, and efficiency. However, unlocking its potential hinges on more than just adoption; employees must develop a nuanced understanding of how to use this technology effectively. 

Organizations must go beyond traditional training approaches and embrace rigorous tracking of learning progress and outcomes specific to Gen AI skills. 

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By measuring key performance indicators (KPIs) such as skill application rates, engagement metrics, and real-world results, leaders can ensure that their teams stay competitive in this rapidly advancing field. 

Why Tracking Gen AI Skills Progress Is Crucial 

Gen AI tools, from text generators to image creation platforms, require a blend of technical expertise and creative application. Without a clear system to measure how employees are learning and applying these tools, organizations risk misaligned training efforts and underwhelming outcomes. 

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Tracking provides actionable insights that guide improvements in learning programs, ensuring employees acquire not only knowledge but also the confidence to leverage Gen AI effectively. 

  1. Skill Application Rates: It’s not enough for employees to complete a training module on Gen AI; organizations must evaluate how well they apply those skills in their roles. For instance, are content teams using Gen AI-generated suggestions to improve efficiency, or are they ignoring its inputs, preferring to generate and edit their own content? 
  1. Engagement Metrics: Measuring time spent on training modules, participation in Gen AI simulations, and frequency of interaction with learning tools can reveal whether employees are actively engaged with the content or merely going through the motions. 
  1. Post-Training Results: The ultimate test of Gen AI learning is its real-world impact. Metrics such as increased productivity, error reduction, and enhanced innovation reflect how effectively employees are utilizing Gen AI to meet organizational goals. 

Client Case Study: Scaling Gen AI Skills Adoption at a Regional Retailer 

A regional retailer illustrates the transformative power of tracking Gen AI learning progress. Facing mounting competition, the company sought to use AI-driven tools to improve marketing personalization and streamline supply chain operations. 

However, initial adoption efforts fell short. Employees struggled to integrate Gen AI applications into their workflows, and training programs yielded inconsistent results. 

To address these challenges, the company partnered with me as a consultant specializing in Gen AI adoption strategies. We implemented a robust tracking system with the following components: 

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  • Baseline Assessments: We tested employees on their familiarity with Gen AI tools and core AI concepts before training began. 
  • Tailored Learning Modules: We customized training to address specific gaps, such as using Gen AI for customer segmentation or predictive analytics. 
  • Real-Time Progress Monitoring: Dashboards provided managers with insights into module completion rates, engagement levels, and assessment scores in real time. 
  • Outcome Tracking: We also measured post-training KPIs, such as increased marketing campaign ROI and reduced inventory mismanagement. 

Within three months, 87% of employees reported confidence in using Gen AI tools, up from just 40% before training. More importantly, the retailer achieved a 15% reduction in inventory errors and a 20% increase in marketing campaign performance, demonstrating the tangible value of targeted, data-driven learning programs. 

Identifying Gen AI Skills Gaps 

Tracking learning progress is particularly valuable in identifying skills gaps, which are often amplified when adopting complex technologies like Gen AI. Many employees may struggle with specific aspects of Gen AI, such as prompt engineering, interpreting AI outputs, or understanding ethical considerations. By analyzing pre- and post-training assessments, organizations can pinpoint these challenges and refine their programs. 

For instance, if data shows that employees consistently perform poorly on tasks related to evaluating AI-generated insights, it could indicate a need for more focused training on critical thinking and contextual judgment. Similarly, if team members excel in basic operations but struggle with advanced applications, leaders can design supplemental modules to close these gaps. 

Generative AI is not a one-size-fits-all tool, and we should not approach its training in that way. Tracking learning outcomes enables organizations to personalize the learning journey for each employee, tailoring it to their specific strengths, weaknesses, and roles. 

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Personalized learning fosters higher engagement and better retention, ensuring employees are not overwhelmed or under-challenged. 

For example, a marketing analyst may need intensive training on creating compelling AI-generated copy, while a data scientist may focus more on configuring AI models for predictive analytics. Tracking data such as individual progress rates and feedback allows organizations to offer customized learning paths that adapt in real-time to employees’ needs. 

Leveraging AI Tools to Track AI Learning 

Ironically, one of the best ways to track learning progress in Gen AI programs is by using AI itself. Advanced learning management systems (LMS) with built-in AI capabilities can analyze employee interactions, generate insights on performance trends, and even recommend personalized training modules. These tools simplify the process of collecting, interpreting, and acting on learning data, allowing leaders to focus on strategic improvements. 

For instance, AI-powered LMS platforms can flag employees who may need additional support, such as those repeatedly scoring below average on AI ethics modules. They can also identify top performers who might be ready for leadership roles in AI adoption initiatives. 

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Best Practices for Tracking Gen AI Learning 

To maximize the impact of tracking, organizations should follow these best practices: 

  1. Define Clear Objectives: Align training goals with strategic business priorities. For Gen AI, this could mean improving innovation rates, reducing repetitive manual tasks, or enhancing customer experiences. 
  1. Integrate Real-World Scenarios: Ensure training programs simulate practical challenges employees are likely to face when using Gen AI tools. This bridges the gap between theory and application. 
  1. Foster a Culture of Feedback: Use both quantitative data and employee feedback to refine training programs. Understanding learners’ experiences helps fine-tune content and delivery methods. 
  1. Continuously Review and Adapt: Gen AI technologies evolve rapidly, so training programs must keep pace. Regularly updating learning content and tracking mechanisms ensures long-term relevance, while managing risks. 

Conclusion: Data-Driven Learning for the Gen AI Era 

The rise of Gen AI presents organizations with incredible opportunities — but also challenges. Without effective tracking of learning progress and outcomes, businesses risk falling short of realizing AI’s full potential. By implementing robust systems to monitor skill acquisition, identify gaps, and personalize learning, leaders can ensure their teams are equipped to thrive in the AI-driven future. 

Tracking learning outcomes isn’t just about measurement; it’s about creating a culture of continuous growth and innovation where employees and AI work together to achieve extraordinary results in the future of work.

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Dr. Gleb Tsipursky

Dr. Gleb Tsipursky

Dr. Gleb Tsipursky, called the “Office Whisperer” by The New York Times, helps tech-forward leaders replace overpriced vendors with staff-built AI solutions. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote seven best-selling books, and his forthcoming book with Georgetown University Press is The Psychology of Generative AI Adoption (2026). Prior to that, he wrote ChatGPT for Leaders and Content Creators (2023). His cutting-edge thought leadership was featured in over 650 articles in prominent venues such as Harvard Business Review, Fortune, and Fast Company. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State. A proud Ukrainian American, Dr. Gleb lives in Columbus, Ohio

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