In this MSDW Podcast episode, Jason Gumpert, podcast host and co-founder of MSDynamicsWorld (MSDW), sits down with C5 Insight’s CEO, Geoff Ables, and Prachi Mishra, Copilot expert from Microsoft, to explore what it really takes to make AI transformation successful.
Together, they explore the promise and pitfalls of generative AI, namely Microsoft Copilot, including the risks of “shelfware,” the cultural and leadership challenges of new technology adoption, and the rise of AI agents as digital coworkers.
Blending firsthand experiences with expert guidance, this discussion helps leaders move beyond skepticism and achieve real business outcomes with AI solutions like Copilot.
AI-Driven Digital Transformation: Experts in Failure, Partners in Success
AI Skepticism, Societal Transformation, and Business Impact
The conversation begins with reflections on the rise of AI and its impact across work and society.
Prachi Mishra shares how generative AI has relieved daily work anxieties, offering a glimpse into its personal productivity benefits. Geoff Ables reflects on living through past technology hype cycles and explains why AI feels fundamentally different. Together, they point to AI’s rapid societal adoption, practical business case studies, and its growing influence even on executive responsibilities.
- 02:01 – Prachi Mishra shares how generative AI has transformed her work and alleviates anxiety from certain tasks.
- 03:30 – Geoff Ables reflects on standard hype cycles and his shift from AI skepticism to impactful transformation.
- 04:40 – AI’s growth rate is the largest societal transformation in recent history, reaching 100 million users in just 2 years.
- 05:00 – Real-world case study on reducing EDI (electronic data interchange) error workload by 30% using AI.
- 06:12 – Geoff Ables shares that forecasters project AI can automate up to 50% of CEO responsibilities (his role).
AI Shelfware, Value Creation & Adoption
The discussion turns to the concept of “shelfware,” when organizations purchase technology but fail to achieve ongoing use and value.
Geoff Ables explains that without adoption strategies and continuous training, even promising AI tools like Copilot won’t deliver on its promises. He highlights the importance of proof-of-value programs that guide teams through real-world applications and ensure lasting adoption.
- 07:20 – Jason Gumpert asks Geoff Ables to explain shelfware.
- 08:00 – The shelfware cycle: companies see the value potential of new technology, purchase the tech, but the software sits on a shelf, delivering little to no value.
- 08:30 – C5 Insight’s Copilot proof of value programs identify relevant Copilot business use cases to ensure employee adoption.
- 09:10 – Without a Copilot adoption strategy and ongoing training, usage declines.
- 10:26 – Shelfware definition: paying for licenses but you’re not able to extract the value of what you’re paying for.
Change Management & Customer Zero
Change management becomes a key discussion point, underscoring its role in making AI adoption stick.
Prachi Mishra notes that even Microsoft’s teams initially struggled to integrate Copilot into daily workflows, emphasizing the importance of structured change management. Geoff Ables adds that most organizations underestimate the human element, often finding retraining people harder than deploying the technology itself. They note that Microsoft partners who adopt a “customer zero” mindset model Copilot adoption internally, building credibility and demonstrating proven strategies to clients.
- 10:38 – Prachi Mishra emphasizes the need for change management and user adoption strategies.
- 12:21 – Geoff Ables addresses the human element of change, explaining habit formation and the challenge of retraining the brain.
- 13:38 – 70% of C5 Insight’s clients initially reach out for help to save failed or failing Microsoft business technology investments.
- 14:22 – Customer zero: make yourself your own customer. C5 Insight embraces AI internally to better understand clients’ challenges and speak to real-world Copilot use cases.
AI Agent Delegation
The conversation expands to AI agents, which go beyond automation to act as digital workers.
Agents can independently handle tasks like lead qualification, allowing teams to scale their efforts more efficiently. While powerful productivity drivers, Geoff Ables notes that adopting agents requires a cultural shift. Together, they point to a future where organizations empower “makers” who can train and shape AI agents to create new business value.
- 16:23 – AI is more than automation: Geoff Ables discusses the role of AI agents.
- 17:03 – Prachi Mishra describes outsourcing work to autonomous Copilot agents to enable scalability.
- 17:48 – Prachi Mishra explains how agents streamline manual tasks like lead qualification.
- 18:48 – Geoff Ables discusses the cultural shift required to adopt AI and the idea of making “makers.”
- 20:50 – Prachi shares how being a Copilot “super user” positioned her as a changemaker within Microsoft.
The Role of Leadership in AI Transformation
The focus shifts to leadership’s critical role in digital transformation success (and failure).
Geoff Ables explains that most AI and digital initiatives fail due to a lack of vision and poor execution, outlining the framework leaders need to succeed. Prachi Mishra adds that Microsoft provides resources and toolkits to help organizations strengthen adoption and guide their teams through change.
- 22:10 – Industry stats show that only 20–40% of digital transformations succeed (download the infographic on the top 10 pitfalls).
- 23:03 – The importance of leadership engagement in AI transformation success.
- 24:04 – Vision + Execution = Success. Execution requires a center of excellence with training, governance, and continuous improvement, not just a project plan.
- 24:55 – Microsoft resources for businesses: Copilot for Sales Success Kit and the Microsoft 365 Center of Excellence.
365 Leadership Summit | September 18-19, 2025 in Denver, CO
The episode concludes with a preview of the upcoming 365 Leadership Summit.
The event is designed for business leaders and change influencers who want to understand how to drive AI transformation from the top without diving into technical training. The summit emphasizes change management, digital strategy, business technology roadmaps, AI-powered leadership, Copilot case studies, and more.
- 26:11 – Geoff Ables invites you to join the 365 Leadership Summit, September 18–19 in Denver, CO: the non-technical, AI-first digital transformation event for business leaders and change influencers.
Designed as a niche event, it equips leaders to align business strategy and Microsoft technology to drive cultural change and sustainable success.
Use promo code MSDW to save $500 on your registration!
At C5 Insight, we call ourselves “Experts in Failure, Partners in Success” because we’ve seen what doesn’t work and know how to help you get it right. We’re committed to being our own customer zero, so you work with a trusted Microsoft Partner who models methods for success.
Contact C5 Insight to keep the conversation going.