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Between Fires and Futures: Real Conversations for Tech Leaders Navigating What’s Now—and What’s Next
Between Fires and Futures: Real Conversations for Tech Leaders Navigating What’s Now—and What’s Next

The Cheapest Decision in IT Is the Most Expensive One: Why Mid-Market Tooling Choices Are Quietly Capping Your AI Strategy with Corey Wisdon

25 May 2026 39:51 Tonya Turrell

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About this episode

What if the technology decision that saved your company money three years ago is the very thing slowing your growth today?

In this season two finale of Between Fires and Futures, Tonya sits with Corey Wisdon to unpack one of the biggest hidden problems in mid-market IT: the long-term cost of “cheap and fast” infrastructure decisions.

Corey shares the story of a $3 million enterprise deployment that took eight months before users could even log in, and how that experience completely changed the way he approaches IT strategy, ServiceNow implementations, and AI adoption today. 

They also dive into the surprising reality behind enterprise deployments, the burnout happening on service desks, and why simplicity, integration, and long-term thinking matter more than ever in 2026.

Tune in to hear:

  •  Why the “fast and cheap” IT decision often becomes the most expensive one later 
  •  The hidden costs of fragmented tool stacks and over-customized platforms 
  •  What really causes enterprise deployments to stall after go-live 
  •  Why many organizations are failing to see ROI from AI tools 
  •  The biggest mistakes companies make when rolling out AI internally 
  •  How poor governance creates “agent sprawl” inside organizations 
  •  Why mid-market companies are underserved by enterprise IT vendors 
  •  The difference between ticketing systems and scalable enterprise platforms 
  •  How RL Canning’s hosted ServiceNow model gets organizations live in just 45 days 
  •  The importance of roadmap thinking instead of reactive technology purchases 
  •  Why simplicity is becoming the most important strategy in modern IT 

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© 2026 Between Fires and Futures: Real Conversations for Tech Leaders Navigating What’s Now—and What’s Next. All rights reserved.

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