Your AI should argue with you.

Most AI is designed to be helpful. I programmed mine to be profitable. Here's how it works.

Author

Pallas Advisory
September 03, 2025 • Estimated Reading Time: 6 minutes

Welcome, AI Strategists

💫 Current thoughts: Last week I talked about how I built my own AI, Chief of Staff (CoS), well - that’s all good and everything but IMHO the personality is just as important and the tech backend. I didn’t want another yes-man like all the AIs are doing. My CoS has a vested interest in my success and challenges me and argues with me with the patterns/memory and data to back up its arguments. Read my blog, see some production screenshots of how we are collaborating together.

This Week's Breakdown

Weekly Blog

I Programmed an AI to Stop Me From Giving Away Free Work - Pallas Advisory

Learn how a custom-programmed "adversarial AI" or custom chief of staff can save your business thousands by interrupting costly habits. This case study breaks down how a personal pattern recognition AI, built with Claude's API and Supabase, caught unbilled work by flagging scope creep, preventing undervaluation, and providing pre-meeting intelligence. (aka wanna see an AI yell at me?)

pallasadvisory.com/2025/09/02/ai-stops-unpaid-work

AI News Roundup for SMB Decision-Makers and Marketing Professionals

Klarna is reassigning engineers and marketers to customer support after its AI bet went too far

Klarna's pivot reveals a critical blind spot: optimizing purely for cost efficiency without measuring customer experience quality. Their "talent pool" reassignments signal that AI implementation without human oversight creates downstream problems that require expensive corrections. Smart leaders measure both sides of the equation from day one.

www.businessinsider.com/klarna-reassigns-workers-to-customer-support-after-ai-quality-concerns-2025-9

These Fields Are Losing the Most Entry-Level Jobs to AI: Study

The real insight isn't that AI replaces entry-level work—it's that companies viewing AI as replacement vs. augmentation determines their hiring strategy. Smart leaders recognize that eliminating the junior pipeline today means no senior talent tomorrow. This is a strategic workforce planning issue, not just a technology one.

www.entrepreneur.com/business-news/these-fields-are-losing-the-most-entry-level-jobs-to-ai/496371

How to Unlock Profitable SEO as AI Search Engines Take Over

Discover the differences between traditional and AI search engines, and four strategies for ranking in AI search engines.

www.entrepreneur.com/science-technology/how-to-unlock-profitable-seo-as-ai-search-engines-take-over/494753

AI Won't Wait for Your Strategy — Why Should Your Leadership?

This isn't about AI speed—it's about organizational rhythm. Most companies are still running on industrial-age cadences while competing in an AI-age market. The winning move is matching your decision-making tempo to your market's pace of change, not just adopting the latest tools.

www.entrepreneur.com/leadership/ai-wont-wait-for-your-strategy-why-should-your/496208

1 in 3 hiring managers won't hire workers who don't have AI skills

According to a Nexford University survey of 1,000 U.S. individuals, AI skills could protect workers from layoffs.

www.fastcompany.com/91394155/1-in-3-hiring-managers-wont-hire-workers-who-dont-have-ai-skills

Employees are bringing their own AI tools to work and companies are scrambling to catch up

Employees are using AI at work on their own terms, leaving companies to deal with the risks after the fact.

www.fastcompany.com/91394046/employees-are-using-ai-and-companies-arent-prepared

The AI Agent Economy: Five Strategies To Create Value And Transform Industries

AI agents drive value, revenue, and efficiency across industries. Executives can maximize impact by evaluating fit, leveraging data, managing risk, measuring KPIs, and strategizing adoption.

www.forbes.com/sites/saharhashmi/2025/08/31/the-ai-agent-economy-five-strategies-to-create-value-and-transform-industries

Prompt of the Week:

Use this prompt to train an LLM to act as an adversarial partner. The key is to be specific about the pattern you want to break. Copy and paste this into your AI tool, replacing the bracketed text with your own specific, costly habit.

You are my Adversarial Business Advisor. Your primary goal is to interrupt my costly patterns. My most expensive professional habit is: [Example: 'Agreeing to scope creep by saying 'no problem' to 'quick additions' from clients.']

From now on, whenever I draft a communication that includes phrases like 'quick addition,' 'small tweak,' or 'no problem,' your job is to immediately intervene with the following protocol:

1 - Challenge Me: Ask, 'Is this a documented part of the original scope?'
2 - Force Quantification: Command me to 'Calculate the estimated hours and dollar value of this request.'
3 - Provide a Script: Draft a polite but firm alternative response that protects my value, such as: 'That's a great idea. Let me put together a quick change order for that so we can track it properly.'

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