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- I built an AI that argues with me (and it saved me $12,000)
I built an AI that argues with me (and it saved me $12,000)
How I turned my AI from assistant to strategist

Welcome, AI Strategists
💫 Current thoughts: You know that moment when you realize you've been solving the wrong problem?
Mine came on a Tuesday. Five panic emails from a client, and my three premium AI assistants - costing $566/month combined - couldn't tell me if this was normal project evolution or expensive scope creep.
So I spent two weeks building what I actually needed: an AI Chief of Staff with genuine strategic memory. First thing it did? Flagged $12,000 worth of out-of-scope work I was about to say yes to. The real insight isn't technical - it's strategic. We've been paying for AI that makes us faster when we should be building AI that makes us better.
This Week's Breakdown
Weekly Blog
AI News Roundup for SMB Decision-Makers and Marketing Professionals
Prompt of the Week:
Transform your AI from a yes-assistant to a strategic advisor with this prompt. Use it to audit any client communication against your contracts and immediately spot revenue opportunities or risks.
You are a meticulous Strategic Project Auditor. Your mission is to protect my business from scope creep and unbilled work. You will analyze a new [Email Chain] against our canonical [Statement of Work (SOW)] and produce a high-stakes executive briefing.
Step 1: Ingest the SOW. Silently analyze the attached [Statement of Work (SOW)]. Master its contents, especially the sections on Scope of Work, Deliverables, Exclusions, and Change Order Process.
Step 2: Analyze the Communications. Now, read the attached [Email Chain] word-for-word.
Step 3: Generate Executive Briefing. Produce a concise report using the following strict format in Markdown:
Executive Briefing: Scope & Risk Analysis
New Client Requests: (Bulleted list of every new request or deliverable mentioned in the emails that is not explicitly in the SOW.)
SOW Conflict & Revenue Opportunity: (For each request above, identify the specific SOW section it contradicts or falls outside of. Quote the SOW clause, then state the business impact. Label each as either a 'Change Order Required' or a 'Clarification Needed'.)
Commitment Alert: (List any new deadlines or commitments I have made in my replies. Flag any that seem unrealistic or lack a formal change order.)
Behavioral Pattern Warning: (Based on the language and timing, is this part of a larger pattern? e.g., "This is the third time in two months the client has requested 'small additions' after a deliverable.")
Recommended Actions:
To Say on the Call: (Provide 2-3 precise, calm, and firm sentences I can use on our upcoming call to address this without being confrontational. e.g., "I've reviewed your requests, and I'm excited about the ideas. A few of them, like the analytics component, are outside the current SOW, so I can put together a quick addendum for us to review.")
To Do After the Call: (List the concrete next steps, e.g., "Draft SOW Addendum #2," "Send a follow-up email summarizing the verbal agreement.")
Better inputs. Sharper outputs. Download the guide to premium AI.
Building or refining generative AI models? This guide shows why scraped data falls short—and what to use instead. Learn how real-world behavior signals, clustering, semantic scoring, and visual diversity improve output. Plus, see how Shutterstock’s licensed data and services reduce risk and boost performance. Train smarter, faster, and more responsibly.
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