In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock are joined by Derek Crager, a seasoned engineer turned AI entrepreneur who shares his journey from blue-collar work to building AI-powered knowledge management solutions. Derek discusses how AI is transforming workplace onboarding, knowledge transfer, and personal productivity, drawing parallels between today's AI revolution and the early days of the internet.

Derek brings a practical perspective on implementing AI in enterprise environments, focusing on his company's voice-powered AI assistant "Pocket Mentor" that helps organizations capture tribal knowledge and streamline employee onboarding. The conversation explores the challenges of extracting expertise from subject matter experts, the importance of having clear business outcomes when adopting AI, and advice for students navigating career choices in an AI-driven world.

Key Takeaways:

• Focus on Business Outcomes Over Buzzwords - Don't implement AI just to check a box or follow trends. Instead, identify specific business problems (like inefficient onboarding or knowledge retention) and then explore how AI can provide practical solutions to those challenges.
• AI Excels at Knowledge Augmentation and Accessibility - AI's greatest strength lies in making organizational knowledge instantly accessible 24/7, without judgment, and at a consistent quality level. This is particularly valuable for onboarding new employees and capturing tribal knowledge from subject matter experts before it walks out the door.
• Take Time to Learn and Evaluate Before Jumping In - The AI wave mirrors the early internet adoption curve and will continue evolving over the next 10-15 years. Organizations and individuals have time to thoughtfully evaluate AI solutions rather than rushing to adopt the first available option, emphasizing the importance of learning practical applications before implementation.

Talent acquisition remains stuck in the past while organizations have drastically evolved. "We still hire like it's 1999," explains Leandro Cartelli, CEO of Lana Talent, highlighting a critical disconnect between modern business needs and outdated hiring practices.

In this episode, Dave and Peter explore with Leandro how successful teams are built through strategic cultural assessment rather than simple skill matching. The conversation reveals the difference between "cultural fit" and "cultural add," and how one retail company reduced their 80% turnover rate by half, saving millions through targeted assessment questions.

Leandro breaks down why remote team success hinges on comprehensive onboarding (which drives 80% better retention) and intentional connection building beyond work tasks. Without deliberate efforts like virtual team activities and structured check-ins, remote work becomes "just a slogan" rather than a successful strategy.

Key Takeaways:

• Culture encompasses both fit and add - assess how candidates navigate existing dynamics while bringing fresh perspectives
• Remote work requires intentional investment - comprehensive onboarding and dedicated connection-building are non-negotiable
• Treat talent acquisition strategically - connect hiring with development plans and performance expectations for real business impact

Getting executive buy-in for transformation requires more than vision – it demands clarity about what will actually change and how success will be measured. Leaders need concrete details about what will look different in their organization, not just high-level strategy.

This episode explores balancing directive consulting with coaching. Modern transformations benefit from proven frameworks combined with coaching conversations that help leaders navigate challenges personally. We also examine measuring system change rather than just activity, understanding that progress is non-linear and involves experimentation cycles.

Key Takeaways

• Close the Vision-Reality Gap - Executives need concrete details about organizational changes, not just strategic concepts
• Blend Consulting with Coaching - Combine proven frameworks with personal coaching conversations
• Measure System Change - Focus on meaningful indicators rather than activity metrics