⬡ Shadow AI & Building Your Policy · Issue 4 of 5 Thursday · July 9, 2026 · Issue #038 Today we start building. Before I get into the framework, one thing I want to be clear about: an AI policy is not a legal document. It doesn't need to be reviewed by a lawyer before it exists. It needs to be reviewed by a lawyer before it becomes binding on employees or clients in high-stakes ways — but the version you write this week is a governance starting point, not a legal instrument. Treat it that way...
4 days ago • 4 min read
⬡ Shadow AI & Building Your Policy · Issue 3 of 5 Wednesday · July 8, 2026 · Issue #038 Before you can write a policy, you need to know what you're governing. Most firms that decide to address AI governance skip straight to the policy document — and end up writing rules around tools they think their team uses, for workflows they assume are the risky ones, based on data they've never actually collected. The policy looks fine on paper. It governs a business that doesn't quite exist. Today's...
5 days ago • 5 min read
⬡ Shadow AI & Building Your Policy · Issue 2 of 5 Tuesday · July 7, 2026 · Issue #038 Let me tell you how a shadow AI incident actually starts. Not the dramatic version. The real one. It starts with someone doing something completely reasonable on a Tuesday afternoon. ⬡ How It Starts · A Composite Scenario Note: The following is a composite scenario drawn from publicly reported incident patterns, not a single documented case. The details are illustrative of how shadow AI incidents typically...
6 days ago • 3 min read
⬡ New Series · Shadow AI & Building Your Policy · Issue 1 of 5 Monday · July 6, 2026 · Issue #038 I want to start this week by naming something that's almost certainly already happening inside your firm right now — and that most firm leaders have been slow to address because addressing it feels awkward. Your team is using AI tools you haven't approved. Not because they're reckless. Because they found something that makes their work faster and nobody told them not to. That's shadow AI. And...
7 days ago • 5 min read
⬡ The Compliance-Ready AI Stack Series · Issue 5 of 5 · The Master Framework Friday · June 27, 2026 · Issue #037 We started Monday with the regulatory landscape. Tuesday: law firms. Wednesday: financial services. Thursday: healthcare. Today we close the series with the framework that underlies all of it. This is what we build to at The Promptory when we're implementing AI in a regulated industry. Not a policy template you fill out once and file away. A six-step operational methodology that,...
10 days ago • 6 min read
⬡ The Compliance-Ready AI Stack Series · Issue 4 of 5 · Healthcare Thursday · July 2, 2026 · Issue #037 Healthcare has the highest stakes and the clearest compliance requirements of any industry in this series. When AI governance fails in law or finance, the consequences are serious: regulatory fines, license exposure, client loss. When AI governance fails in healthcare, the consequences can include patient harm. That's not a rhetorical escalation — it's why HIPAA enforcement is criminal as...
11 days ago • 5 min read
⬡ The Compliance-Ready AI Stack Series · Issue 3 of 5 · Financial Services Wednesday · July 1, 2026 · Issue #037 Financial services firms are in the most paradoxical position in professional services AI right now. On the productivity side, the gains are extraordinary. AI-powered portfolio analysis, automated reporting, intelligent client follow-up, compliance monitoring — the tools that were enterprise-only two years ago are now accessible to a five-person RIA for under $200/month. On the...
12 days ago • 5 min read
COMPLIANCE SERIES #2 of 5 — ⬡ The Compliance-Ready AI Stack Series · Issue 2 of 5 · Legal Tuesday · June 30, 2026 · Issue #037 The legal industry has a complicated relationship with AI. On one hand, attorneys are among the highest-value users of AI in any professional services category — the research compression alone is transformative. A task that took four hours of database work now takes forty minutes. Contract review that required a junior associate's full day now surfaces every critical...
14 days ago • 6 min read
⬡ New Series · The Compliance-Ready AI Stack · Issue 1 of 5 Monday · June 29, 2026 · Issue #037 Something has changed in the professional services AI conversation — and I want to name it directly before we spend a week on it. Six months ago, the primary conversation was adoption. How do you get your team to use AI? Which tools are worth trying? How do you make a business case for the subscription? That conversation is over. Adoption happened. Broadly, quickly, and in most cases without...
14 days ago • 4 min read