Field notes on AI in business
Practical writing on AI, automation and the day-to-day work of running a business. From the team that builds and runs AI systems.
AI compliance
Contract Lifecycle Management AI and the Outside Counsel Approval Question
Contract Lifecycle Management AI and the Outside Counsel Approval Question A general counsel at a mid-size financial services firm recently told me something that stuck with me. They had been feeding...
Basel IsmailMay 25, 2026
AI compliance
Solo and Small Firm Lawyers, Cost Pressure, and the Compliant AI Stack
Solo and Small Firm Lawyers, Cost Pressure, and the Compliant AI Stack A solo practitioner in family law is paying $79/month for a general-purpose AI writing tool, feeding it client intake notes, and...
Basel IsmailMay 25, 2026
AI compliance
Trade Secret Audits: The Quarterly Review Every Mid-Market Company Now Needs
Trade Secret Audits: The Quarterly Review Every Mid-Market Company Now Needs A trade secret audit sounds like one of those things your outside counsel recommends once, you nod politely, and then...
Basel IsmailMay 24, 2026
AI compliance
Litigation Holds Now Have to Cover AI Chat Histories
Litigation Holds Now Have to Cover AI Chat Histories If your litigation hold procedures were last updated before 2023, they almost certainly have a gap. A big one. Employees across your organization...
Basel IsmailMay 24, 2026
AI compliance
Why Your Information Security Awareness Training Probably Does Not Mention AI
Why Your Information Security Awareness Training Probably Does Not Mention AI I just reviewed the security awareness training programs from three major vendors. Combined, they serve something like...
Basel IsmailMay 24, 2026
AI compliance
Shadow Procurement: When Departments Buy AI Tools Without Telling IT
Shadow Procurement: When Departments Buy AI Tools Without Telling IT A marketing manager signs up for an AI copywriting tool. Puts it on the corporate card. The tool ingests the company's brand...
Basel IsmailMay 24, 2026
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AI compliance
Data Loss Prevention in the AI Era: Why DLP Tools From 2019 Cannot Help You
Data Loss Prevention in the AI Era: Why DLP Tools From 2019 Cannot Help You Your DLP system is probably very good at catching someone emailing a spreadsheet full of Social Security numbers to a Gmail...
Basel IsmailMay 24, 2026
AI compliance
ABA Formal Opinion 512: The Generative AI Ethics Rules Every Lawyer Should Have Read
ABA Formal Opinion 512: The Generative AI Ethics Rules Every Lawyer Should Have Read The ABA Standing Committee on Ethics and Professional Responsibility released Formal Opinion 512 on July 29, 2024,...
Basel IsmailMay 24, 2026
AI compliance
Prompt Injection Attacks and the Trade Secret Exfiltration Vector Nobody Saw Coming
Prompt Injection Attacks and the Trade Secret Exfiltration Vector Nobody Saw Coming A researcher named Johann Rehberger demonstrated in late 2023 that he could get ChatGPT to exfiltrate conversation...
Basel IsmailMay 23, 2026
AI compliance
Retrieval Augmented Generation and the Confidentiality Boundary You Keep Forgetting
Retrieval Augmented Generation and the Confidentiality Boundary You Keep Forgetting RAG is the architecture everyone reaches for when they want an LLM to answer questions about internal documents....
Basel IsmailMay 23, 2026
AI compliance
Why Training a Model on Your Proprietary Data Is a Bigger Decision Than Most CISOs Realize
Why Training a Model on Your Proprietary Data Is a Bigger Decision Than Most CISOs Realize A vendor pitches you on fine-tuning a large language model with your proprietary data. Better outputs,...
Basel IsmailMay 23, 2026
AI compliance
Model Cards, Data Sheets, and the Vendor Disclosures You Should Be Demanding
Model Cards, Data Sheets, and the Vendor Disclosures You Should Be Demanding I've been reviewing AI vendor documentation for regulated clients for the better part of three years now, and I can tell...
Basel IsmailMay 23, 2026
1,319 articles