I Finally Cracked Why AI Agent Projects Keep Failing—And I Built a Workbook with 11 Prompts So You Can Fix Yours Tomorrow

I’ve been watching teams burn months trying to automate their most important workflows. Smart engineers. Good models. Ambitious roadmaps.

And then three months in: stalled agents, bloated scope, frustrated leadership, and humans who’ve completely checked out.

Meanwhile, down the hall, another team automated three “boring” tasks and freed up 30% of their week.

The difference isn’t talent or technology. It’s where they started.

The teams that win don’t start with the core of the workflow—the part that requires deep expertise and judgment. They start with the edges: data preparation, QA, synthesis, handoffs, packaging. The mechanical stuff that surrounds the valuable work.

This is obvious in hindsight, but almost nobody does it. Because the edges feel like the boring parts. The stuff you do before and after the “real work.”

That framing is the trap.

Here’s what’s in this post:

• The edge-first framework — What “edge” actually means, why core-first automation fails, and how to identify the five edge categories in any workflow you touch

• The trust problem nobody mentions — Why AI automation is an organizational trust exercise, not a technical project, and how attacking edges first earns you the right to eventually touch the core

• Field notes by role — What edge-first automation looks like for PMs, engineering leads, sales, customer success, and ops—including the common traps each role falls into and where to start

• Eleven companion prompts — A full prompt manual that turns an LLM into a genuine thinking partner. These aren’t checklists; they give the model enough context on edge-first automation to reason alongside you. Including:

  • The Workflow Compass — Map a messy workflow and find the edges. For anyone staring at a process they don’t fully understand yet.

  • Edge Discovery Through Human Friction — Surface edges through where time and energy disappear. For teams who know something’s wrong but can’t name it.

  • The Fast-Win Filter — Pick which edge to automate first. For when you have multiple candidates and need to prioritize.

  • Design a Semi-Manual Version-0 — Build something shippable in days, not months. For avoiding the agent moonshot trap.

  • Extract Tribal Knowledge Safely — Get people to share the unwritten rules. For when you need insider knowledge without triggering defensiveness.

  • Communicate Edge Automation Without Threatening People — Tell your team what’s happening. For leaders who need buy-in, not fear.

  • Edge Stacking ROI Projection — Model the compounding value of multiple edges. For building the case for continued investment.

  • Am I Ready to Approach the Core? — Honest readiness assessment. For when you’re tempted to move inward and need a sanity check.

  • Diagnose Why My Last Agent Project Failed — Postmortem framework. For anyone whose automation stalled and wants to understand why.

  • Build an Edge Automation Portfolio — Find opportunities across adjacent teams. For scaling beyond your own workflow.

  • The One-Prompt Guided Journey — End-to-end walkthrough in a single conversation. For people who want the whole experience without switching prompts.

• The path inward — How edge automation positions you to eventually automate the core, and how to know when you’re actually ready

This is field notes from what I’m actually seeing, not theory. No vapor statistics, no Gartner citations—just the pattern that separates teams that ship from teams that stall.

If you’ve had an automation project fail, or you’re about to start one and want to avoid the obvious mistakes, this framework will save you months. Grab the prompts, read the breakdown, and let me know where you’re looking to automate.