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Most companies say they're using AI, but only 30% have even created an acceptable use policy. Alane Boyd and Micah Johnson are back with part 2 of their AI fluency series, and this time they're going deep on the organizational level: the six milestones that separate companies dabbling with AI from those actually building with it.

If your team is experimenting with AI tools but you have no committee, no shared systems, and no way to measure who knows what, you're building on sand. This episode gives you the framework to change that, no matter where your organization is starting from.

In this episode, you'll learn:

• How to build an acceptable use AI policy that evolves as your tools and workflows evolve
• Why AI champions matter, and how to identify and use the right people on your team
• How to measure your team's AI fluency using milestone tracking across roles
• The system for sharing wins and roadblocks so AI knowledge doesn't stay siloed
• Why clean data is non-negotiable, and why AI can't fix your messy folder system for you
• How to document your workflows so anyone can understand them, no technical background required

If you're serious about building an organization that doesn't just use AI but grows with it, this episode gives you the exact roadmap. Press play, your team will thank you.

If you haven't listened to part 1 yet, start there first: The 5 Individual Milestones of AI Fluency.

Education & Resources

Claude Cowork Masterclass

🛠️ Tools & Platforms Mentioned

• Claude Cowork
• n8n
• Slack
• ClickUp
• Asana
• Basecamp
• Skype
• Dropbox / Shared Drive

This episode is brought to you by Biggest Goal.

Every quarter your team spends evaluating AI is a quarter your competitors spend shipping. Most leaders feel the pressure but get stuck between ignoring AI and getting it wrong. More tools and more demos won't fix it. What actually works is hands-on training for the people doing the work.

For more information about our AI education programs, visit biggestgoal.ai.

Upcoming Sessions:

• Free Claude Cowork Webinar
• Claude Cowork Masterclass
• Claude Deep Dive Series

Connect with Us:

• TikTok
• LinkedIn
• YouTube
• Community

Disclosure: Some links are affiliate links, meaning we may earn a commission at no extra cost to you. Thanks for supporting the podcast!

Send us Fan Mail

Most business leaders talk about AI adoption. But Alane and Micah are asking the real question. How do you actually measure it?

In this episode, they introduce a five-milestone framework for tracking individual AI fluency on your team. This framework was built from a real gap Micah observed at a recent COO conference where everyone agreed the topic mattered but nobody had answers.

If AI adoption at your company feels more like chaos than progress, there's a good chance your team has no shared baseline and no way to know who's moving forward and who's stuck. Alane and Micah make the case that undefined fluency goals are a business problem, and that the fix is easier than most leaders think.

In this episode, you'll learn:

• How to define milestone one so every team member has a clear, achievable starting point with Cowork
• Why Skills, Folders, and Connectors are the baseline every team member should hit, and why that alone drives major efficiency gains
• How one team member spent 5 minutes on something that now saves 45 minutes every single day
• The two-track model (individual vs. organizational) and why measuring only one of them leaves half the picture missing

If you're ready to stop guessing about where your team stands with AI and start building a measurable path forward, this episode gives you the exact framework to do it.

Upcoming Education Sessions:

• Free Claude Cowork Webinar
• Free Claude Cowork Masterclass
• Claude Deep Dive Series

🛠️ Tools & Platforms Mentioned

• Cowork
• Claude
• n8n
• Python
• APIs & Webhooks
• ChatGPT

Learn More about our AI Agent + RAG Cohort:

Not sure how to get started with AI? Join our 4-week AI Agent Development Cohort, where you’ll build real AI agents and automation. No technical background required.

The July 20th cohort is filling fast. Save your spot and sign up today.

This episode is brought to you by Biggest Goal.

Every quarter your team spends evaluating AI is a quarter your competitors spend shipping. Most leaders feel the pressure but get stuck between ignoring AI and getting it wrong. More tools and more demos won't fix it. What actually works is hands-on training for the people doing the work.

For more information about our AI education programs, visit biggestgoal.ai.

Upcoming Sessions:

• Free Claude Cowork Webinar
• Claude Cowork Masterclass
• Claude Deep Dive Series

Connect with Us:

• TikTok
• LinkedIn
• YouTube
• Community

Disclosure: Some links are affiliate links, meaning we may earn a commission at no extra cost to you. Thanks for supporting the podcast!

Send us Fan Mail

Forget the full AI agent. Alane Boyd and Micah Johnson are making the case that Claude Cowork Skills are the most powerful, most overlooked feature in AI right now. One slash command. Twenty-five steps handled. Consistently, every time.

If your business relies on humans doing the same thing the right way every single time, you already know how that goes. The inconsistency, the retraining, the quiet shortcuts. It's not a people problem. It's a systems problem. Claude Skills are the fix.

In this episode:

• What a Skill actually is: part SOP, part system, part micro app
• How to standardize your team's work without retraining anyone
• Why adding a deal to your CRM is secretly a 25-step process, and how one command handles all of it
• How Skills connect to your tools and run automatically in the background
• How to build your first Skill the right way: start simple, iterate, don't wait for perfect
• How Alane's workshop analysis Skill works exactly like she does, so she doesn't have to be the one doing it

If your team is doing the same thing five different ways and you're ready to fix that, start here.

Upcoming Education Sessions:

• Free Claude Cowork Webinar
• Free Claude Cowork Masterclass
• Claude Deep Dive Series

🛠️ Tools & Platforms Mentioned

• Claude Cowork
• Grain
• ClickUp
• Pipedrive
• Copper
• n8n
• Python
• MCP (Model Context Protocol)
• Anthropic

Learn More about our AI Agent + RAG Cohort:

Not sure how to get started with AI? Join our 4-week AI Agent Development Cohort, where you’ll build real AI agents and automation. No technical background required.

The July 20th cohort is filling fast. Save your spot and sign up today.

This episode is brought to you by Biggest Goal.

Every quarter your team spends evaluating AI is a quarter your competitors spend shipping. Most leaders feel the pressure but get stuck between ignoring AI and getting it wrong. More tools and more demos won't fix it. What actually works is hands-on training for the people doing the work.

For more information about our AI education programs, visit biggestgoal.ai.

Upcoming Sessions:

• Free Claude Cowork Webinar
• Claude Cowork Masterclass
• Claude Deep Dive Series

Connect with Us:

• TikTok
• LinkedIn
• YouTube
• Community

Disclosure: Some links are affiliate links, meaning we may earn a commission at no extra cost to you. Thanks for supporting the podcast!