Welcome to Functional Executives, where Veer and Jim Boswell bring pragmatic, real-world insights from the front lines of technology, finance, and strategy for mid-market companies. In this episode, Veer and Jim Boswell dive into the world of AI in business—from the early hype of ChatGPT, to the challenges of AI maturity, to the practical pitfalls and opportunities facing organizations today.

They discuss why most mid-sized businesses are still at the starting gate with AI, explore the growing need for organizational literacy and certifications, and highlight the importance of moving beyond flashy AI projects to make the technology a seamless part of daily operations. Along the way, they share personal experiences, debate risk and regulation, and challenge the fear-driven binary thinking that often holds companies back. Whether you’re a senior executive or hands-on operator, you’ll get actionable advice and thought-provoking commentary on how to leverage AI while navigating the messy realities—and opportunities—of digital transformation.

Veer and Jim Boswell discuss how most mid-sized companies are at the very low end of the AI maturity curve, despite leadership often believing they are much further along

Jim Boswell introduces the idea that companies must move beyond viewing AI as a novelty, integrating it as a fundamental aspect of daily work—much like past shifts to digital and mobile-first mindsets

Veer emphasizes that early AI policies should rely on existing principles (like email or data sharing policies) and common sense, rather than creating fear-driven, overly restrictive rules

Jim Boswell argues that focusing on high-profile AI initiatives is less valuable than embedding AI into everyday workflows and making it almost "invisible" through practical adoption and proficiency

Veer points out that many companies already operate in gray technical areas (like non-compliant Excel spreadsheets driving key decisions) and that similar flexibility should be considered with AI

Connect With Us

• Reach out if you’re interested in deeper education, workshops, or one-on-one strategy sessions tailored to your business’s AI journey. Our contact info is in the show notes!