Happy Thursday! Welcome back to HOW TO // AI.
Sooner or later, someone at your company asks: "Are we ready for AI?" For almost every team I talk to, the honest answer is "partly, and we're not sure which part."
After 25+ years in enterprise IT across virtualization, cloud, and networking, I built three ways to find out. One is free and takes three minutes.
🧭 Readiness isn't one thing. It's six.
Most teams are strong in two or three of these and exposed in the rest. When I score IT teams, the weak spots are usually data and security: AI assistants surfacing files nobody meant to share, and people pasting work into AI tools you haven't approved.
The free AI Readiness Score asks ten questions and shows where you stand on all six, plus your red flags. It's built for IT leaders, but if you're the one who'll be asked, take it yourself first.
📄 Want the full picture?
The AI Readiness Report covers all 24 questions and turns your answers into a 35+ page plan: your top risks with a fix for each, quick wins, and a 90-day plan. I review every one personally, and it's yours within 48 hours.
$497, or $1,997 with a 60-minute strategy call.
📜 Need an AI policy this month?
The fastest fix for shadow AI isn't a ban. It's a one-page policy plus one approved tool. Write it yourself with the free template in my shadow AI policy guide, or let the AI Use Policy Pack write five documents for your company from a 5-minute form.
$149, in Word and PDF, with one free regeneration or a full refund within 14 days. It isn't legal advice, so have HR and legal review it.
🎯 Try this in five minutes
If you run IT, sign in as an ordinary employee and search your shared drives or SharePoint for salary, pricing and termination. Anything that comes back, an AI assistant connected to your documents could surface too.
🕵️ Plus: is that job posting real?
My tenth free tool checks a job posting or recruiter message for scam signs and ghost jobs, and marks every red flag in it. Three free checks a day, no sign-up.
🎁 Share HOW TO // AI, get free rewards
Forward this to whoever at your company will be asked "are we ready for AI?" 1 referral gets you the Complete Kit Vault, and 10 get you my book, Amplified, free.
📬 In case you missed it
Ten free AI tools, no sign-up
Summarize anything, quiz yourself, answer an email, plan a certification, or check a job posting. Nothing stored.
What does AI actually know about you?
A ten-minute audit for ChatGPT, Claude, and Gemini, plus the one rule that matters more than every toggle.
🤔 Got questions?
Has someone already asked whether your company is ready for AI? Tell me how you answered. Email [email protected] and you just might be featured in an upcoming issue!
Stay curious, stick with it, and watch your skills grow week by week!
Until next time :)
-David
P.S. If your day job is enterprise IT - VMware, cloud, storage, infrastructure - I write a second newsletter that decodes that world in ten minutes a week: Subscribe to Enterprise Techie →
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