Bridging the Generational Skills Gap in Retail With AI-Enhanced Training
The retail industry is entering a pivotal period as it braces for a significant shift in its workforce. Nearly 60 percent of retail employees aged 55 and older are expected to retire within the next five years, according to the whitepaper From Boomers to Zoomer: How to Bridge the Frontline Generational Gap. This shift presents a challenge beyond talent shortages; it threatens the transfer of institutional knowledge and frontline expertise that has powered retail operations for decades.
Many retail executives are already voicing concern that their organizations will struggle to retain this expertise. Without a structured approach to preserving and passing on key skills, retailers risk a growing disconnect between what the next generation of employees knows and what the job increasingly requires.
One core issue fueling this divide is inadequate training for younger workers. Subpar onboarding, limited coaching, and generic learning content have contributed to a widening skills gap. In fact, 30 percent of employees say they're likely to leave their current retail role due to insufficient training and development. This points to a clear imperative: retail leaders must rethink how they prepare employees for today’s customer expectations and tomorrow’s demands.
Artificial intelligence is increasingly emerging as a strategic lever to address this gap. It's not fully replacing human instruction, but amplifying its effectiveness. One promising application is the use of AI-driven roleplays, which simulate a range of real-world customer interactions, from routine service requests to emotionally charged encounters.
These AI-powered simulations allow employees to practice navigating difficult scenarios in a controlled, judgment-free environment. Unlike traditional training methods that may be limited by staffing, time or consistency, simulated conversations are always available, adaptable to specific roles, and capable of adjusting to the user’s progress. This training builds practical skills, but more importantly, it cultivates the confidence and emotional resilience needed to perform under pressure. When an employee has faced dozens of realistic scenarios during training, they're more prepared to respond with clarity and professionalism in the moment.
Consider a retail associate dealing with a frustrated customer who received the wrong product during the holiday rush. An AI-simulated roleplay can help that employee learn to de-escalate the situation, offer appropriate solutions, and maintain brand reputation, all before ever setting foot on the sales floor. Through exposure to these complex interactions, employees gain experience managing uncertainty, connecting with customers, and sustaining team morale.
Managers benefit as well. AI can analyze performance across simulated scenarios and provide insight into skills gaps and coaching opportunities.
One store manager shared the frustration this type of solution could address: “Without proper training … it creates a cycle where experienced team members are constantly interrupted to explain things, reducing overall productivity. I wish there were structured resources to help new employees get up to speed faster.”
AI simulations do not replace the need for strong human leadership. They free up time and resources so trainers and mentors can focus on higher-level coaching, career development, and culture. In this way, AI helps bridge the generational divide by enhancing human-led learning with modern, scalable tools.
Retail’s workforce challenges are real, and they're growing. However, with AI-driven training, particularly through conversation simulations that mirror the complexity of real-life customer service, retailers can equip the next generation with the confidence, knowledge and resilience to succeed. Now is the time to act. Retail leaders who invest in modern training strategies today will be better prepared to navigate tomorrow’s workforce transitions and unlock the full potential of their teams. The business outcomes — from sales targets to employee retention — will be clear.
Sam Dorison is the co-founder and CEO of ReflexAI, a company that equips human support and contact centers with scalable AI tools that deliver advanced roleplay simulations and intelligent quality assurance.
Sam Dorison is the Co-founder and CEO of ReflexAI, with expertise in AI strategy and product deployment across industries like mental health, cybersecurity, and smart cities. Previously, he was Chief Strategy & Innovation Officer at The Trevor Project, leading teams in crisis services, training, and research. Dorison has also worked at McKinsey & Company and Harvard Kennedy School. He graduated summa cum laude and Phi Beta Kappa from Princeton University, holds an LL.M. from Cambridge University, and a master’s degree from University College London as a Marshall Scholar.
