The starter kit Jay gives every leader and team he works with. Five sections of ten tips each — read it in 20 minutes, ship something this afternoon.
Before tools and prompts, mindset. Most AI failures aren't technical — they're how you frame the question.
An intern with the world's reading list — but they still need direction, examples, and review. Stop expecting magic. Start delegating well.
Try: When you're stuck, ask "How would I brief an intern on this?" Then paste that into your AI.
The leaders who win with AI aren't coders — they're people who can articulate what "good" looks like. Specificity is the skill that matters.
Try: Before each prompt, write the one-sentence outcome you want. Paste it in.
Stop using it to type faster. Start using it to think clearer. The best uses involve back-and-forth, not one-shot generation.
Try: After your first response, ask "What's wrong with this answer?" — and then "Fix it."
Don't reinvent. Keep a personal library. Most of your "AI productivity" comes from reusing the same 20 prompts.
Try: Open a Notion or Google Doc called "My Prompts." Paste every prompt that worked.
It's usually "I haven't tried asking that way yet." Before assuming a limit, try three different angles.
Try: Next time you think "AI can't do X," rephrase three times.
Would I pay $20 to skip this task? Then run it through AI. Stop hand-typing what a prompt can do in 30 seconds.
Try: Pick the dumbest, most repetitive thing on today's list. Prompt it instead.
The fastest way to a clear strategy is to draft 10 bad versions in 20 minutes with AI. Then pick.
Try: Ask AI for 10 different angles on your next decision. Pick the best three.
Anyone can prompt. What separates good output from great is editing — and editing is taste, which is yours alone.
Try: Spend 70% of your AI time reviewing/editing. 30% prompting.
Teams that hesitate lose 6 months while competitors compound. Imperfect adoption beats perfect strategy.
Try: Pick one workflow this week. Apply AI imperfectly. Iterate.
You'll discover the real limits by doing, not by reading. Push every workflow. Map the walls.
Try: Pick one core workflow. Use AI for every step this week. Note what breaks.
A few prompt patterns do 80% of the heavy lifting. Master these and you'll never write a vague prompt again.
"Write for a busy CFO who needs the bottom line in 30 seconds" produces wildly different output than "summarize this." Audience is half the brief.
Try: Add "Audience: [specific role + context]" to every prompt for a week.
"You are X. Your goal is Y. Constraints: A, B, C." This three-part structure removes 90% of the back-and-forth.
Try: Use the role/goal/constraint pattern for your next 5 prompts.
Paste 2 examples of what good looks like. AI matches patterns better than it follows instructions.
Try: Find an example of the output you want. Paste it. Ask for "more like this."
Before you generate, ask: "What questions would I need to answer to get great output here?" Then answer those.
Try: For your next big prompt, ask "What do you need from me to make this great?"
"Don't use the word 'leverage.' Don't open with a question." Negative constraints sharpen output faster than positive ones.
Try: Add a "Don't do" list to your next 3 prompts.
"Give me three drafts, each with a different angle." One great, one decent, one terrible — the terrible one teaches you what to avoid.
Try: Default to "give me 3 versions" on creative work.
"Now act as a skeptical senior exec and list the 5 weakest points in what you just wrote." Self-critique catches problems you'd miss.
Try: End every important draft with "what's wrong with this?"
"Write me a prompt that will produce X" works embarrassingly well. AI is great at prompting itself.
Try: Next time you're stuck, ask AI to write a prompt that would solve your problem.
"Here's my first pass — make it sharper" almost always beats "write something for me."
Try: Always write 100 words of your own first. Then improve with AI.
Your standing instructions live in the system prompt. Only the task changes. This is the speed unlock.
Try: Build a Notion page with 5 "system prompts" and reuse them.
These are the highest-ROI plug-ins for an average knowledge worker's week. Pick three and watch your output change in two weeks.
Paste 20 unread email subjects and ask: "Which 3 need a response today? Which 3 can wait? Which can be archived?"
Try: Tomorrow morning, triage before opening your inbox.
Paste raw notes and ask: "Pull out decisions made, action items with owners, and open questions."
Try: After your next meeting, prompt this. Send the result.
Most "polish" is starting from a blank page. Have AI draft. Spend your real energy on the edit.
Try: Next blog/post/email: AI drafts in 5, you edit in 25.
"Here's a CSV. What are the 3 surprising things in this data?" AI is a remarkable junior analyst.
Try: Run last month's report through AI and ask what you missed.
Before a big call: "Argue against my plan as a hostile board member would." Then "Now defend my plan."
Try: Steelman your next big decision before the meeting.
ChatGPT for creative + general, Claude for nuanced writing + analysis, Perplexity for research with citations.
Try: Compare the same prompt across ChatGPT, Claude, and Perplexity once this week.
Hour-long talk → tweet thread, LinkedIn post, blog article, newsletter, 3 short clips, 1 quote graphic. One piece of work, week of content.
Try: Take your last recorded talk and extract 7 pieces this week.
"How might this email be misread by [recipient]? Where are the ambiguities?"
Try: Pre-mortem your next sensitive email before hitting send.
"Explain [thing] like I'm a smart 12-year-old. Then like I'm an expert. Then point out where those two answers disagree."
Try: Pick a topic you've been avoiding. Apply this. Time it.
Wisprflow or phone voice typing → paste into AI → "polish this for [audience]." You'll triple your writing speed.
Try: Voice-dictate your next 5 messages. Polish with AI.
The bottleneck isn't tooling. It's getting humans to actually use it. These tips are about culture, not code.
Don't pilot "AI for marketing." Pilot "AI for our weekly content brief." Specific, owned by one person, measurable.
Try: Name the ONE workflow you'll change first. Write it down today.
Every team has one person who's already messing around with AI on their own time. Find them. Make them the visible lead.
Try: Identify your AI champion this week. Give them air cover.
End every standup with: "What prompt saved you time this week?" Shared learning compounds. Hidden learning evaporates.
Try: Add this question to your next team meeting agenda.
Get the team in a room. List the 10 most common tasks. Build a prompt template for each, together.
Try: Schedule a 60-min "prompt sprint" with your team this month.
"AI is going to make us all redundant" is the silent killer of adoption. Address it: "AI replaces tasks, not people who think."
Try: Put "job impact" on your next team agenda. Don't dodge it.
Adoption fails when "use AI" is added on top of existing workload. Carve out 2 hours/week of "explore AI" time.
Try: Block 2 hours this Friday for your team to play with AI.
People learn AI by watching peers struggle and succeed. A 90-min team session beats five 30-min individual ones.
Try: Run a 90-min team AI session instead of solo onboarding.
When someone saves 4 hours with AI, broadcast it. Slack channel, all-hands, leader email.
Try: Create #ai-wins in your team's chat tool this week.
Tool sprawl kills adoption. Pick ChatGPT or Claude as the team default. Pick one image tool. One transcription tool.
Try: Pick your team's "official 3" AI tools this week.
Pick a number. When you hit it, do something visible. Adoption is a story, not a memo.
Try: Set your team's first AI milestone today. Pick the celebration.
Once AI is in your workflow, two questions matter: is it costing us anything risky, and is it actually paying off?
Use enterprise versions (ChatGPT Team, Claude Enterprise) or local models for PII, contracts, financials.
Try: Audit what your team has pasted this month. Adjust.
You don't need 30 pages. You need: "Use these tools. Never these. Always disclose AI use in [contexts]."
Try: Draft your one-page policy using the AI Use Policy Starter.
Customer-facing content, regulated industries, legal docs — disclose. Internal emails — don't bother.
Try: Make your disclosure rule explicit this week.
"We're more productive with AI" is unprovable. "We saved 12 hours this week" is. Multiply by hourly rate. Communicate the number.
Try: Set up a simple hours-saved tracker in your team's spreadsheet.
$20/month for ChatGPT Plus is the best ROI in your tech stack. Don't cheap out at the start.
Try: Audit your team's AI subscriptions. Upgrade where it matters.
One doc, updated weekly: "Workflow → time saved → who did it." After 8 weeks you have a story.
Try: Start your team's AI Wins doc today.
Three questions before you ship AI output: 1) Did I verify the facts? 2) Does it sound like me/us? 3) Could it hurt anyone if wrong?
Try: Print this checklist. Tape it near your screen.
Your "what AI fails at for us" list is more valuable than the success list. It tells you where humans still earn their salary.
Try: Make a #ai-fails channel.
AI tools are improving faster than any other category. The tool that lost 6 months ago may be winning now.
Try: Block one 60-min "tool audit" on your calendar every 90 days.
AI as "a project" sunsets. AI as "the way we deliver more output with the same team" lives in the P&L forever.
Try: In your next leadership update, tie your top AI win to a P&L line.
You don't need to act on all 50. Pick three. Ship one this week. The leaders who win with AI are not the ones who read the most — they're the ones who shipped one bad version first.
Take the 90-second AI Opportunity Quiz, or book a 20-minute call.