In this episode of The RaaP, Kyle and Kyle break down the most common—and most costly—pitfalls organizations encounter during the IT sourcing and vendor selection process.

From the ubiquitous “Yes, we can” trap, to hidden-fee mazes, to sales-to-delivery handoff failures, to misleading baseline quotes, to the ticking clock of renewal time bombs, the team walks through how these issues show up in real projects and what buyers can do to avoid them.

They also discuss why vendors aren’t acting maliciously—just operating within their incentives—and why experienced partners can spot these patterns early. The conversation is tactical, practical, and directly rooted in lessons from the field.