Cup of Wit

Essay archive

Essays

Field notes, operating-model questions, and practical AI strategy for making AI useful inside real organizations.

2026

Agents & AutomationOperating Models
I Built an AI Agent That Reads My Invoices Before I Do.

Build #4 in the automation stack — and the hardest debugging session yet.

AI StrategyOperating Models
Your Team Is Already Using AI. You Just Haven't Decided How Yet.

The teams that get AI governance right don't write more rules. They make clearer decisions.

Prompting & ContextOperating Models
What AI Can't Remember — And Why That's Your Competitive Edge

Every time you close a chat window, AI forgets everything.

Agents & AutomationAI Strategy
The AI Agent Promised to Do Your Work. Here's Why It Didn't

You were told it would handle it.

Agents & AutomationPrompting & Context
I Built an AI Research Agent. Here's the Unfiltered Account.

What the tutorials don't show you — including the part where the AI confidently led me in circles, and why that's actually the most important lesson.

Agents & AutomationOperating Models
I Automated My Content Pipeline. Here's the Honest Account.

The build-in-public post I wish existed — including the ratio nobody talks about, and what it means differently depending on your role.

Prompting & Context
Stop Searching AI. Start Managing It

Most people treat AI like a smarter Google.

AI StrategyOperating Models
AI Does Not Replace Human Judgment — It Reveals Its Absence

For leaders who believe their organizations are ready for AI — and haven't asked what they're actually ready for.

Here's something nobody in the AI conversation wants to say out loud.

Prompting & ContextAI Strategy
The Real Skill of the AI Age Is Not Prompting — It's Questioning

Everyone is learning how to prompt.

Operating ModelsAI Strategy
The Quiet Danger of AI: Decision-Making Without Thinking

For leaders who think AI is making their teams smarter — and haven't noticed what it might also be making them.

Let me say something uncomfortable.

Operating ModelsAI Strategy
From Pilot to Production: Why Most AI Projects Never Scale (And How to Fix That)

Your company ran a successful AI pilot. Leadership loved the demo. The team celebrated. Six months later, it's still a pilot.

AI StrategyAgents & Automation
5 Signs Your AI Strategy Is Really Just an Automation Strategy (And Why That's a Problem)

A practical guide for leaders who think they're doing AI transformation — but haven't made the leap yet.

Let me be direct: most organizations that say they have an "AI strategy" don't.

Operating ModelsPrompting & Context
8 Ways to Make AI Outputs Trustworthy: Evidence, Traceability, and QA

A practical checklist for leaders who need AI work to be defensible, auditable, and compliance-ready.

Let me be direct: the #1 reason enterprise AI initiatives stall isn't the technology. It's trust.

Prompting & ContextOperating Models
7 Red Flags Your Prompting Problem Is Actually a Process Problem

You’ve spent hours tweaking your AI prompts.

Prompting & Context
How to “Brief” AI Like a Human Teammate (So It Actually Understands the Assignment)

You wouldn't give a colleague a one-line instruction for a complex deliverable. AI deserves the same discipline.

You wouldn't walk up to a colleague and say: "Write something about business capabilities." Yet that's exactly how most people prompt AI. They type vague…

Agents & AutomationPrompting & Context
How to Turn AI Into Your Assistant (So You Become Faster, Not Replaceable)

AI won't replace you. But someone using AI effectively will. Here's how to stay on the right side of that gap.

The fear is real: "If AI can do my work, why do they need me?" I hear this from experienced consultants, business architects, and analysts who've spent decades…

Prompting & Context
From Prompting to Context Engineering: The Shift That Changes Everything

Most teams are still playing the prompt game.

Prompting & ContextOperating Models
The Real Bottleneck Isn't AI—It's Ambiguity

AI doesn't clarify ambiguity — it multiplies it. How to define problems clearly enough that AI can actually help.

An AI transformation project stalled after six months of intensive work.

Prompting & Context
How to Engineer Better Inputs: The Data/Context Moves That Beat Better Prompts

I spent two hours crafting the perfect prompt. The AI output was still garbage.

AI Strategy
Why "AI for AI's Sake" Fails: How Smart Organizations Tie Every Initiative to Business Outcomes

The organizations achieving real ROI on AI share one discipline: they never start with the technology.

It's never a great idea to adopt AI for its own sake, but the AI-fueled organizations have clear business objectives for their AI technology initiatives.

Operating ModelsAI Strategy
How to Get Stakeholder Buy-In for AI Outputs (Without Sounding Like You’re Outsourcing Thinking)

The quality of your AI-assisted work doesn't matter if stakeholders don't trust how you produced it. Five language patterns that change that.

I've seen this mistake kill deals more than once. A consultant delivers a brilliant analysis—sharp insights, solid recommendations, 40 pages of documentation…

Operating Models
The Hidden Risk: AI Increases Mistakes When Accountability Is Unclear

When AI makes a consequential decision and no one is accountable, the entire organization pays the price.

Here's a scenario that should terrify every executive: Your AI-powered procurement system just rejected a \$2M vendor contract. The vendor threatens legal…

2025

Prompting & ContextOperating Models
How to Run AI Through a Human Workflow: Ask → Verify → Decide

Every consultant I know has the same problem with AI: they love what it drafts, but they don't trust it enough to hit "send."