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Why Your Team Keeps Tripping Over Gen AI—And How to Fix It

If your team is still stumbling with Gen AI use, it’s time to stop blaming the tools — and start investing strategically in the people wielding them.

Dr. Gleb TsipurskybyDr. Gleb Tsipursky
March 11, 2025
in Tech
Reading Time: 5 mins read
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Why Your Team Keeps Tripping Over Gen AI—And How to Fix It

Gen AI promises big wins — increased efficiency, groundbreaking innovation, and sharper competitive edges — but those gains vanish quickly when your team isn’t properly equipped.

  • Custom Gen AI training should be role-specific, not one-size-fits-all, for better results.
  • Hands-on exercises and real-world scenarios improve adoption and long-term competence in Gen AI.
  • Gen AI training must be inclusive, offering varied formats and support to engage all employees

Organizations are racing toward generative AI (Gen AI) implementation, but many find themselves stumbling rather than sprinting. 

Gen AI promises big wins — increased efficiency, groundbreaking innovation, and sharper competitive edges — but those gains vanish quickly when your team isn’t properly equipped. 

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To stop wasting potential, leaders must craft training programs as precise and adaptive as the Gen AI technology itself, tailored directly to employee roles, experience, and practical workflows. 

Real success in Gen AI hinges not on generic introductions but on deeply customized, role-specific mastery. 

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Why Generic Gen AI Training Misses the Mark — And How to Target It Right 

Standardized training is tempting; it’s simple, scalable, and cost-effective. Unfortunately, it’s also largely ineffective. 

Employees across different roles rarely share identical workflows or responsibilities, which means a one-size-fits-all approach only scratches the surface of Gen AI’s capabilities. 

Instead, create laser-focused training modules customized to each job’s specific demands. Lawyers don’t need Gen AI explained through marketing jargon; they need actionable insights on document analysis, research acceleration, and automated drafting. 

Paralegals and support staff, meanwhile, thrive on automating routine workflows like scheduling and client communications. 

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Consider a hospital system: clinicians would leverage Gen AI for accurate diagnosis and predictive patient care, whereas administrative teams could boost efficiency in patient scheduling or billing systems. 

With Gen AI itself making personalized learning increasingly feasible at scale, there’s no excuse not to deliver targeted training that resonates directly with each employee’s daily tasks. 

From Theory to Action: Bridging Gen AI Knowledge and Real-World Skills 

Theoretical Gen AI training may enlighten, but without immediate practical application, your employees will quickly forget — or worse, disregard — what they’ve learned. To build lasting competence and confidence, every Gen AI program should integrate hands-on exercises, real-world scenarios, and relevant, relatable case studies. 

Give your team scenarios that mimic their everyday challenges, prompting them to use Gen AI tools practically — whether it’s automating client email replies, analyzing legal briefs, or optimizing internal communications. 

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Employees become confident Gen AI users only when they consistently experience the technology’s real-world value firsthand. 

Accessibility Isn’t Optional: Making Gen AI Training Inclusive and Fair 

Not all employees approach Gen AI with the same comfort, skill level, or learning style. Effective training embraces this diversity by delivering material through multiple formats—interactive modules, video tutorials, written guides, and live demonstrations. Offering a menu of options empowers your workforce to engage comfortably and effectively, no matter their technical background. 

Additionally, inclusivity means proactively addressing potential biases within Gen AI training materials and tools. Unchecked bias undermines credibility and can cause real-world harm, a risk underscored by extensive research from Harvard Business Review. To mitigate this risk, establish regular audits of both your Gen AI platforms and your training content, perhaps guided by proven frameworks such as Microsoft’s Responsible AI principles. 

Real inclusivity also requires additional support mechanisms—peer mentoring, supplemental sessions, or dedicated coaching for those who struggle. The goal is to ensure every employee feels not just able but enthusiastic about developing and applying Gen AI skills. 

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Real-World Impact: A Law Firm’s Leap from Hesitation to Gen AI Excellence 

A mid-sized law firm recognized it was falling behind competitors who had embraced Gen AI. Leaders asked me to spearhead a customized Gen AI training strategy designed explicitly around role-based applications. Attorneys explored tools for rapid research, document drafting, and case risk assessment. Paralegals and administrative staff mastered automation of scheduling and routine client communication. 

The critical breakthrough? Shifting training from conceptual lectures to practical workshops where employees applied Gen AI directly to their daily tasks. Employees quickly understood not only what Gen AI was but exactly how it could simplify their workloads. 

Within six months, measurable outcomes emerged clearly: 

  • Gen AI tool adoption surged dramatically, jumping from below 20% to over 85% 
  • Attorneys reported efficiency improvements of at least 30% in critical tasks like drafting and document analysis 
  • Administrative and paralegal staff saved 20% of the time previously wasted on routine tasks, allowing them to focus on higher-value work 

This targeted, practical approach didn’t just educate—it transformed productivity, effectiveness, and employee satisfaction. 

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Overcoming Common Gen AI Pitfalls (Because Problems Will Happen) 

Despite enormous upside, implementing Gen AI training often hits predictable snags: 

  • Resistance to Change: Fear of the unknown—and worries about automation replacing jobs—often provoke anxiety. Address this head-on with clear, ongoing communication emphasizing success stories and the career-enhancing benefits of Gen AI skills. 
  • Engagement Drop-off: Maintaining employee attention is challenging. Introduce gamification elements—quizzes, leaderboards, or badges—to encourage sustained participation and enthusiasm. 
  • Resource Constraints: Successful training requires investment—both financial and human. Securing buy-in from senior leadership, complete with budget and dedicated training resources, is essential to ensuring program sustainability and alignment with organizational goals. 

Bringing It All Together: Gen AI Training as a Strategic Advantage 

Your organization’s Gen AI future isn’t a question of technology—it’s a question of people. Effective training should introduce Gen AI as well as embed it seamlessly into workflows, role by role, person by person. When done right, the result isn’t merely higher adoption rates but meaningful transformations: employees who proactively use Gen AI to drive efficiency, innovation, and competitive leadership. 

If your team is still stumbling with Gen AI, it’s time to stop blaming the tool—and start investing strategically in the people wielding it. 

 

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Tags: AIHuman Resources (HR)LeadershipWorkforce
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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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