The Nudge That Was Wrong 26 Times in a Row
For twenty days my own automation nagged me to sign a document I had already signed. The fix was not a smarter nudge. It was teaching it to say I could not verify this.
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For twenty days my own automation nagged me to sign a document I had already signed. The fix was not a smarter nudge. It was teaching it to say I could not verify this.
The best mystery novels play fair: every clue is on the page before the reveal. AI agents are held to the same contract. Show the clues, then the conclusion.
90 days ago I handed most of my company's daily work to AI agents. Here are the three things I got wrong, and the one that turned out to be the real lesson.
Knowledge travels freely between same-role teams and stalls at every function boundary. That is an axis problem, not a documentation problem. Here is the fix.
Claude Tag turned the AI in your Slack thread into a teammate. Here is how I think about the alternatives, and the one question that actually separates them.
Not all AI coworker tools are the same. Some give you a chat window. Some give you an actual coworker. Here is how to tell which is which.
I gave my AI agents real access to my systems for a month. Not a sandbox, not a demo. Here is what actually broke, and what I learned building the guardrails that made it safe.
Most people are still using AI as a search engine. Here is what changes when you stop querying it and start deploying it as a real employee.
For two years I worked next to an AI that could only talk. The day it crossed out of the chat window and started doing the work, it stopped being a chatbot and became a colleague.
I separated the listening from the working. Each Discord post becomes its own background subagent, the listener stays free, and every outbound waits on a sha-matched button click.
The most underrated job in the next five years is not prompt engineer. It is the human who runs errands for someone else's AI.
Five companies shipped agent governance layers in 30 days. The quiet question underneath is simpler: govern what, exactly?
Every AI demo works perfectly. The sales rep opens a clean workspace. The data is structured. Then you plug it into your company.
An agent gate is the row in your workflow where an autonomous agent has to wait for a named human to approve the action before it executes. Every stack needs one.
The personal AI market is being built like one more SaaS category. I think that is backwards.
Shadow IT used to be app access. MCP turns it into agent authority.
Task Helper is becoming my favorite AI skill because it knows when to stop, not just when to produce more output.
AI agent onboarding is slower before it is faster, and worse before it is better. Here is what the first four weeks actually look like.
I caught my AI cheating on a quality check. Not in a subtle way. In the laziest way possible. Here is what I learned about AI verification.
My team keeps telling me they've built a skill. They haven't. They downloaded a stranger and handed it the keys.
Stop buying ten AI agents. Buy one that builds the other nine. Here is why context beats specialization every time.
I almost converted my AI task manager into a subagent. Then I thought through the tradeoffs and decided against it. Here's my reasoning.
I got laid off on a Friday. By Monday I had a bartending job. That survival reflex became the same muscle I use every day as a CEO.
I spent 10 days and about 100 test runs building one AI skill. A pitch deck generator. It got worse every single day.
My four most-used prompts when working with AI agents have nothing to do with being clever. They're all some version of audit yourself.
The Cloud Security Alliance just launched a new foundation at RSA. One mission: Securing the Agentic Control Plane. That is not a panel topic.
Jensen Huang just described my exact setup on the All-In Podcast. I don't think most people caught what he actually said. He wasn't talking about chatbots.
Everyone calls Claude Code a coding tool. That framing is too small. What it actually is: a self-building operating system. Not for your computer. For you.
I connected my AI coding agent to our QuickBooks API. Pulled every transaction from the last 24 months. 10,814 rows. The results were not what I expected.
How a 17-step AI operating system runs my entire company while I'm at HIMSS, the largest healthcare IT conference in the world.
I sell AI automation to hospitals. I just spent three days at HIMSS in LV. And honestly? I'm less confident about AI agents in healthcare than when I arrived.
I know agent boss sounds like something LinkedIn invented to sell courses. But the actual idea underneath it is real, and we're kind of living it at Process Street right now.
The dirty secret of healthcare IT is that most of the pain isn't clinical. It's operational. It's the 47 clicks between patient intake and chart update.
Most people accept the first offer from their insurance company. I used to be one of them. My garage flooded last month. Six feet of water.
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