Is this a fit?
Run paid AI workshops for businesses — for sales teams, marketing teams, executives, or entire companies. One client can be worth more than dozens of small consumer transactions.
Skills to bring or develop
- AI Tool Expertise
- Training & Facilitation
- Process Design
- Change Management
The starting sequence
- Build your AI expertise portfolio
- Create workshop curriculum
- Offer free AI audits
- Land first corporate clients
- Scale with online courses and group training
What the work involves
You don't need to be an AI researcher or engineer. You need to be genuinely ahead of most business owners — comfortable inside tools like ChatGPT, Claude, Notion AI, or Make.com — and able to translate that fluency into plain language a 52-year-old operations manager can act on Monday morning. The real skill here is facilitation and change management, not coding. You're helping teams unlearn old habits and build new ones, which means you'll hit resistance, skepticism, and the occasional 'we tried that and it didn't work.' If you can stay patient, curious, and concrete in those moments, you have what it takes. If you need everyone to be excited before you can move forward, this will wear you out fast.
Find your first customers
Treat this customer profile as a starting hypothesis. Talk to people in this role and find out what they already do, what it costs them, and whether they want help.
Role
VP of Operations / COO
Company size
50-500 employees
Industry
Professional Services / Mid-Market
Problems to investigate
- Team is curious about AI but nobody knows where to start
- Wasting money on AI tools nobody actually uses
- Competitors adopting AI faster
- No internal AI expertise
- Fear of AI replacing jobs creating resistance
Channels to test
- Local Networking
- Referrals
- Content Marketing
First launch approach
Offer free 30-minute AI readiness assessments to 20 businesses, convert top prospects to paid workshops
Ways to find your first customer
- Post daily AI tips and tool reviews on LinkedIn
- Offer free lunch-and-learn AI sessions to local businesses
- Partner with HR consultants and business coaches
- Speak at local chamber of commerce and industry events
- Create a "Top 10 AI Tools for [Industry]" guide as lead magnet
Content ideas
- How AI saved this team 20 hours/week
- 5 AI tools every operations team should use
- The real cost of NOT using AI in 2026
- AI implementation mistakes that waste money
Shape the offer & delivery
These are example packages to adapt, not current market rates or promises of sales. Choose one deliverable, set a revision limit, and test the scope with a real buyer before expanding.
AI Audit
$1,500 example price
- Tool assessment for your team
- AI readiness scorecard
- Top 5 quick wins report
- 1-hour debrief call
Team Workshop
$3,500 example price
- Half-day hands-on training
- Custom to your industry
- Prompt library for your workflows
- Recording + materials
- 30-day follow-up support
AI Transformation
$8,000/mo example price
- Full implementation partner
- Weekly training sessions
- Custom SOPs for every department
- Tool selection + setup
- Ongoing optimization + support
Build and deliver the offer
Service delivery
Packages
Name
Team Workshop
Deliverables
- Half-day or full-day AI training session for a team
- Custom exercises using their real workflows
Timeline
1 day, scheduled 2-3 weeks out
Included in this example
- Pre-session survey of team's current AI usage/gaps
- Slide deck + exercise materials
- Follow-up resource guide
Outside this example
- Ongoing 1:1 coaching
- Custom tool implementation
Name
Coaching Cohort
Deliverables
- 6-week group coaching program, weekly live sessions
Timeline
6 weeks
Included in this example
- Weekly live session
- Private community/Slack for the cohort
- Homework assignments applying AI to real work tasks
Name
Enterprise Retainer
Deliverables
- Ongoing AI adoption advisory for an organization
Timeline
Monthly, quarterly-planned
Included in this example
- Recurring training sessions
- Tool evaluation and recommendations
- Change-management support
Client onboarding
Step
Send a pre-training survey asking about the team's current AI tools, comfort level, and specific pain points
Who handles it
client
Step
Review a sample of the team's real work tasks so exercises use their actual context, not generic examples
Who handles it
client
Step
Confirm the org's AI usage policy/restrictions before designing exercises (some industries restrict specific tools)
Who handles it
you
Kickoff conversation
- Understand the real barrier: is it skill, fear, unclear use cases, or organizational policy?
- Identify 2-3 concrete workflows to use as live exercise material
- Set the success metric for the engagement — usually a specific behavior change, not just "awareness"
Your launch roadmap
Work through the phases at your own pace. Durations and task hours are estimates; client conversations, sales, and other outcomes depend on the response you receive. Growth and exit steps are optional later decisions.
0 of 14 tasks checked
01 · Foundation 1 week · suggested pace
Build expertise portfolio and workshop materials
Build a repeatable process for assessing a company's AI readiness — tools used, processes, pain points, quick wins
Target deliverable: AI Audit Checklist + Scorecard
Tool examples: Notion, Google Docs
Planning allowance: 6 hours
Create a half-day hands-on workshop with exercises, prompt libraries, and take-home materials
Target deliverable: Workshop deck + materials
Tool examples: Google Slides, Notion, Canva
Planning allowance: 10 hours · AI can assist; review the output
Create a 20-minute sample training video showing your teaching style and AI expertise
Target deliverable: Demo reel for prospects
Tool examples: Loom, ChatGPT
Planning allowance: 4 hours · AI can assist; review the output
02 · Launch 2 weeks · suggested pace
Land first 2-3 corporate training clients
Reach out to 20 businesses offering free 30-minute AI readiness assessment
Target deliverable: 10 audits completed
Tool examples: LinkedIn, Email, Loom
Planning allowance: 10 hours
Run a free "AI for Your Business" webinar to build authority and capture leads
Target deliverable: 50+ webinar attendees
Tool examples: Zoom, LinkedIn, Canva
Planning allowance: 8 hours
Follow up with audit prospects, pitch paid workshops
Target deliverable: 2-3 paid workshops booked
Tool examples: Email, Zoom, Google Docs
Planning allowance: 6 hours
03 · Scale 2 months · suggested pace
Build recurring revenue and online presence
Package workshop content into a self-paced online course for passive revenue
Target deliverable: Online course live
Tool examples: Teachable, Loom, Canva
Planning allowance: 20 hours · AI can assist; review the output
Post AI insights 5x/week on LinkedIn, grow to 5K+ followers
Target deliverable: Authority in AI training niche
Tool examples: LinkedIn, ChatGPT
Planning allowance: 10 hours · AI can assist; review the output
Pitch ongoing AI transformation packages to workshop graduates
Target deliverable: 2 transformation retainers
Tool examples: Email, Zoom, Notion
Planning allowance: 8 hours
04 · Exit 60 days · suggested pace
Prepare your AI coaching and training business for sale, acquisition, or hands-off operation
Create comprehensive standard operating procedures covering every repeatable process in your AI coaching and training business — client onboarding, delivery workflows, billing, and support. A buyer needs to run this without you.
Target deliverable: Complete SOP handbook with video walkthroughs
Tool examples: Notion, Loom, Google Docs
Planning allowance: 12 hours · AI can assist; review the output
Record the questions this step raises for your business, location, and circumstances. Confirm requirements and assumptions with current official sources and a qualified professional before acting.
Target deliverable: Valuation estimate with supporting financials
Tool examples: Google Sheets, ChatGPT
Planning allowance: 6 hours · AI can assist; review the output
Organize all financial records, contracts, customer data, IP documentation, and legal documents into a virtual data room that a buyer or their advisor can review.
Target deliverable: Organized virtual data room
Tool examples: Google Drive, Google Sheets
Planning allowance: 10 hours
Identify every area where the business depends on you personally. Delegate, automate, or document each one. Test by taking 2 weeks off and measuring impact.
Target deliverable: Owner dependency scorecard (before/after)
Tool examples: Notion, Zapier, Slack
Planning allowance: 20 hours
Create a teaser document (blind profile) for your AI coaching and training business and either list on marketplaces (Acquire.com, Flippa, Quiet Light) or reach out directly to 5-10 potential acquirers.
Target deliverable: Teaser document + 5-10 buyer conversations started
Tool examples: Acquire.com, Google Docs, Email
Planning allowance: 8 hours · AI can assist; review the output
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Tools, budget & effort
These are tools named in the original playbook, offered as examples to evaluate. Check current capabilities, pricing, licensing, and data handling with the provider before subscribing. Start with the tools you already have.
- ChatGPT
- Claude
- Midjourney
- Notion
- Loom
Tools to evaluate
Item
A presentation/workshop deck tool (Google Slides or Canva)
Why consider it
Paid workshops need real, polished delivery materials
Item
Zoom or similar for virtual workshop delivery
Why consider it
Many workshop clients want a remote-friendly option
Workshop delivery and virtual training
- Zoom Webinars
- Butter
- Loom
Client deliverable and SOP documentation
- Notion
- Google Docs/Slides
- Tango
CRM and client pipeline management
- HubSpot CRM
- Notion CRM template
- Calendly
Make the numbers your own
Include setup, subscriptions, selling, fulfillment, revisions, support, and your time. Use your actual inputs and compare a cautious case with a better case.
Open the experiment calculator →AI roles & prompt templates
Assign a clear job, provide approved inputs, and review the result. These are role and prompt ideas; this page does not run AI or connect your accounts.
Content Writer
Help me draft 3 hands-on exercises for a sales-team AI workshop
Sales Optimizer
Help me write an outreach message pitching a half-day AI workshop to a mid-size company
Copy a prompt, then add your context
Replace the bracketed placeholders. Use information you have permission to share, ask for sources, and check every factual or numerical claim.
Build a custom AI readiness audit for a prospective client
I run an AI coaching and training business. I have a discovery call coming up with a [INDUSTRY] company that has [NUMBER] employees and currently uses [LIST THEIR TOOLS]. They want to understand how AI could help their team. Create a 15-question AI readiness audit I can send them before the call. The audit should cover: 1. Current workflow pain points (5 questions) 2. Existing tech stack and data hygiene (4 questions) 3. Team AI literacy and comfort level (3 questions) 4. Leadership buy-in and budget signals (3 questions) For each question, include: the question itself, why I'm asking it (my internal note), and what a 'low readiness' vs 'high readiness' answer looks like. Format it as a Google Form-ready list I can copy directly. Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
Write a workshop agenda and facilitator guide for a half-day AI training session
I'm delivering a half-day (4-hour) AI training workshop to a team of [NUMBER] people at a [INDUSTRY] company. Their primary roles are [JOB TITLES]. Their current AI experience level is [beginner/intermediate]. The business outcomes they want are [LIST 2-3 GOALS]. Create a complete facilitator guide including: - A timed agenda broken into 30-minute blocks - Learning objectives for each block - 2-3 hands-on activities or exercises per block (specific, not generic) - Suggested prompts or demos I can run live - Common participant questions and how to answer them - A 10-minute 'next steps' closing that leaves them with a concrete action plan Make the activities specific to their industry and job roles. Avoid generic 'explore ChatGPT' exercises — give me real workflow-connected tasks they'll actually use Monday morning. Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
Create a 90-day AI implementation SOP for a client's team
I need to write a 90-day AI implementation plan for a client. Here are their details: - Industry: [INDUSTRY] - Team size: [NUMBER] - Current tools they use: [LIST] - Top 3 workflow bottlenecks they want to solve with AI: [LIST] - Budget for new AI tools: [MONTHLY BUDGET] - Technical comfort of team: [LOW/MEDIUM/HIGH] Create a 90-day phased implementation SOP with: - Phase 1 (Days 1-30): Foundation — tool selection, team onboarding, first wins - Phase 2 (Days 31-60): Integration — embedding AI into existing workflows, building internal prompts library - Phase 3 (Days 61-90): Optimization — measuring time saved, expanding use cases, reducing friction For each phase include: weekly milestones, who owns each task (role-based), success metrics, and a 'what to do if stuck' troubleshooting note. Format as a table I can drop into Notion or Google Docs. Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
Generate a proposal and pricing package for an AI training engagement
I'm an AI coaching and training consultant. I just completed a discovery call with a potential client. Here's what I learned: - Company: [INDUSTRY], [NUMBER] employees, [REVENUE RANGE if known] - Their problem: [DESCRIBE PAIN POINT IN 2-3 SENTENCES] - What they asked for: [WHAT THEY SAID THEY WANT] - What I think they actually need: [YOUR ASSESSMENT] - Their timeline: [WHEN THEY WANT TO START] - Budget signals: [WHAT THEY SAID OR HINTED] Write a professional proposal (not a template — a real one) that includes: 1. A one-paragraph 'situation summary' that proves I listened 2. Three tiered packages (Starter, Growth, Transformation) with clear deliverables, timelines, and prices in the range of $2,500 / $5,500 / $10,000 3. What's included and explicitly excluded in each tier 4. A ROI framing paragraph (time saved, errors reduced, capacity gained) 5. A clear call to action with a 7-day decision window Tone: confident, specific, no fluff. Write it as if I'm sending it today. Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
What a working week could look like
This is an example cadence. Include time for customer conversations, review, and admin; reduce the scope to fit your available hours.
What
Chief of Staff check-in — share one client win, one stuck point, one tool you tested
When
Daily · 15 min
What
LinkedIn content or direct outreach to niche contacts
When
Mon & Wed · 45 min
What
Tool and prompt testing — stay current, document what's useful for clients
When
Fri · 1h
What
Client delivery review — audit SOPs or workshop materials for accuracy and freshness
When
Sun · 1h
Problems to plan for
Use these playbook prompts to question your plan. Pricing, channels, and delivery models should be tested with your own customers.
Training people on AI tools instead of solving their actual business problems
Start every engagement with a workflow audit. Identify 2-3 specific tasks that eat time or cause errors. Design your training around those exact tasks. Measure time saved, not features learned.
Underpricing because you feel like you're 'just teaching'
Price by project or outcome, not by the hour. Anchor your pricing to the value delivered, not your time spent.
Taking on clients without change management buy-in from leadership
Before signing any engagement, require a 30-minute call with the decision-maker (not just the team lead). Confirm they'll attend the kickoff, send an internal communication endorsing the training, and set aside 30 minutes/week for follow-up during implementation. Make this a contract requirement.
Building a curriculum once and never updating it as AI tools change
Schedule a monthly 2-hour 'curriculum audit' block in your calendar. Update one module, test your demos, and note any tool changes. Treat your training materials like a living product, not a finished document.
Trying to serve every industry instead of picking a niche
After your first 3-5 clients, look at where you got results. Pick one or two industries and go deep. Build industry-specific case studies, prompts libraries, and SOPs. Your marketing becomes easier and your close rate goes up.
Your first small test
- Choose one customer. Find five people who have the problem described in this guide.
- Show one useful sample. Ask about their current process, priorities, and objections.
- Offer a clearly scoped pilot. Agree on deliverables, a price to test, and what success means.
- Record the evidence. Track responses, costs, hours, and what the buyer actually used. Decide whether to continue, change, or pause.
Explore related ideas
Adapted from Ashley’s Waymaker side-hustle playbooks, imported October 15, 2026. This is a published snapshot, not a live connection to your Waymaker account. Source examples are planning material, not verified customer outcomes. Explore Waymaker.