Sidecar Sync
Sidecar Sync
Amith Nagarajan and Mallory Mejias
The 95% Problem: Fixing What’s Broken in Enterprise AI | 116
39 minutes Posted Jan 8, 2026 at 11:00 am.
Zombie Apocalypse & Beverage Goblins
Why 95% of Enterprise AI Projects Fail
The System vs. Feature Problem
Workflow-First Implementation
The Tail Wagging the Dog: When IT Leads AI Strategy
Consumer-Grade Tools vs. Enterprise Expectations
Should Associations Wait on AI from Their Vendors?
Partnerships, Not Products: Rethinking Implementation
Governance, Change & Measuring What Matters
Wrapping Up
0:00
39:11
Download MP3
Show notes
Send us Fan Mail In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias dig into the startling findings of a recent MIT study: 95% of enterprise AI initiatives are failing to deliver measurable impact. Why are so many organizations investing in AI only to watch their efforts fizzle? Mallory and Amith unpack 10 core reasons for these failures—ranging from building chat-first features instead of end-to-end workflows, to skipping the unglamorous data cleanup that powers real results...