Advanced LLM Usage for CEOs and Executives Series
This short article series is designed to help owners, entrepreneurs, and senior staff use AI LLMs far better. As a past CTO and VP of Engineering and someone who has used AI every day in many ways for several years now, I have found most do not understand its limitations or its most powerful features either. These eight articles reveal not just tips and tricks, but major traps in using AI—especially when it gives confidently stated, credible-sounding answers that are wrong.
Your AI Can Hold a Library and Still Miss the Facts That Matter
Article 4 of 8
The hidden cause of shallow AI output
Executives often blame the model when an answer is generic. The more common problem is that the system has been given a vague question, a few facts, and no reliable picture of the business. A good consultant would ask questions before prescribing. AI should be forced to do the same.
The context window is the information available to the model for the current work. Some products also offer projects, knowledge bases, or memory features, but the underlying principle remains: the answer can only be as company-specific as the relevant context the system can retrieve and use.
Capacity is not attention
A large context window is useful, but it is not proof that every fact will receive equal attention. The 2024 research paper ‘Lost in the Middle’ found that model performance could decline when relevant information was buried in the middle of a long context. Models continue to improve, but the management lesson survives: relevance, structure, and source quality matter more than the raw number of pages uploaded.
Think of context as a conference-room table. Put the right contract, financial statement, customer research, and decision memo on the table and the conversation improves. Cover the table with outdated drafts, duplicated files, random articles, and contradictory numbers and the important document becomes harder to see.
Build a CEO Context Pack
- Objective: the decision or work product required.
- Company brief: stage, history, business model, offers, customers, and economics.
- Strategy: where the company intends to win and what it refuses to become.
- Current truth: approved KPIs, financials, priorities, constraints, and dates.
- Source hierarchy: which files control when sources conflict.
- Definitions: what terms such as lead, customer, margin, qualified, or complete mean here.
- Guardrails: privacy, legal, brand, approval, and risk limits.
- Output test: format, evidence, citations, assumptions, and acceptance criteria.
Click the image above to learn about Bob’s Trusted Adviser program for SMBs that want to scale.
For a free business assessment Zoom call on what is holding your company back that you may not see, click here. Bob Norton does all these personally. Offer good for CEOs and owners at companies with at least $500K in revenue or 6+ employees. A complete written report is available to anyone for $1,200.
ADVANCED MOVE – COPY/PASTE PROMPT Use only the attached sources for company-specific claims. Begin by listing the files you can access, their dates, and any conflicts. Treat [NAME THE AUTHORITATIVE FILES] as controlling. Cite the filename and page or section for every material fact. If the answer is not in the sources, say “not found” and ask for the missing information. |
Create specialists, not one giant junk drawer
I use separate projects for separate domains: marketing, strategy, clients, health, and other areas. Each specialist receives the context required for its job. That produces better focus and reduces the chance that old, irrelevant, or contradictory information contaminates the answer.
Also know the privacy terms of the product and account you use. Business and enterprise plans may provide additional contractual and administrative protections; consumer settings can differ. Context engineering and data governance belong in the same conversation.
The advanced question is not, “How large is the context window?” It is, “Did we put the right truth on the table, and can the model show us where every important claim came from?”
ADVANCED LLM WEBINAR
COMING SOON
Most owners never get beyond prompts, drafts, and occasional research. This fall, AirTight Management will host an Advanced LLMs for CEOs live series built around real business work: better decisions, faster research, smarter workflows, stronger management systems, and more than 100 practical moves you can use—with some tools and models available nowhere else.
The launch price is $29 for the complete live, four-webinar series, recordings, and downloadable tools. Click here to register.