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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!

Send us Fan Mail

Here's something that'll mess with your head: ChatGPT and Claude have zero memory. Every message you send, the model reads your entire conversation from scratch, answers, then forgets everything. When these tools claim they "remember" you, that's not the AI. It's separate software making judgment calls about you, and you never see it happen.

If you've ever wondered why AI gives inconsistent outputs or seems to lose the plot, this episode connects the dots. Alane Boyd and Micah Johnson break down why relying on automatic AI memory quietly works against your team.

In this episode:

• Why AI memory is really judgment calls stacked on judgment calls
• How bad memories become invisible and skew everything after them
• Why context bleeds between clients without warning
• How every team member ends up with a different "source of truth"
• The file-based system that puts you in control of what AI remembers
• Why Biggest Goal shut off automatic memory at the organization level (and nobody noticed)

Memory is just context. Once you control the context, the outputs finally get consistent.

Upcoming Education Sessions:

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

Tools/Platforms Mentioned

• ChatGPT - AI chat interface with automatic memory feature
• Claude - Anthropic's AI assistant with memory functionality
• Claude Desktop - Desktop application for Claude
• Claude Cowork - Business/team version of Claude
• OpenAI Codex - Code-understanding AI model
• Obsidian - Knowledge management and note-taking app
• Google Drive - Cloud storage service for file syncing
• Dropbox - Cloud storage service for file syncing

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

What happens when someone goes on vacation and all their AI work becomes inaccessible? Alane Boyd and Micah Johnson tackle the collaboration crisis emerging as teams adopt Claude for real work.

This isn't really about vacations. It's about work getting siloed in individual AI sessions where no one else can access the research, problem-solving, and progress being made. When AI tools actually do the work instead of just providing suggestions, everything changes.

In this episode, you'll learn:

• Why AI work gets trapped in individual sessions and how to prevent it
• The paradigm shift from sharing AI chats to sharing AI outputs
• How to use Connectors and Skills to automatically save progress to shared systems
• Real examples of ClickUp integration that keeps work flowing
• Why this collaboration problem affects daily teamwork, not just vacations
• Practical systems for making AI enhance collaboration instead of breaking it

If you're ready to stop treating Claude like a personal diary and start using it as the collaborative tool it's meant to be, this episode shows you exactly how.

Upcoming Education Sessions:

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

Tools/Platforms Mentioned

• Claude
• Project Management Tools: ClickUp, Asana, Monday.com
• Help Scout
• Pipedrive
• Salesforce
• Front
• Slack
• Teams
• Dropbox
• Google Drive
• SharePoint

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

Before you connect AI to anything, decide where each type of information live, and never let it live in two places. Alane Boyd and Micah Johnson tackle the biggest mistake teams make when implementing AI tools like Claude.

If you've ever wondered why your AI gives inconsistent answers or pulls outdated information, this episode reveals the culprit. The hosts get real about why downloading files and re-uploading them to AI projects creates chaos.

In this episode, you'll learn:

• How to establish a single source of truth that works for both humans and AI
• Why duplicate files kill AI accuracy before you even realize it's happening
• The knowledge layer approach to connecting AI with your existing systems
• Real examples of what goes wrong when information lives in multiple places
• How to properly connect Claude to SharePoint, Google Drive, and other storage without creating copies
• Why standardization isn't optional when AI tools are part of your workflow

If you're ready to stop making AI guess where to find information and start giving it access to the right source, this episode shows you exactly how.

Upcoming Education Sessions:

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

Tools/Platforms Mentioned

• Claude
• SharePoint
• Google Drive
• Dropbox
• Box
• PM Tools: ClickUp, Asana, Monday.com
• Grain
• Microsoft 365
• Ignite
• Rippling
• Pipedrive
• Obsidian
• Trainual

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

Your project management tool is capable of so much more than task tracking, but most teams are using only 10% of its potential. Alane Boyd and Micah Johnson break down the harsh reality of why that remaining 90% is limiting your team, workflows, and AI automation efforts.

If you've ever felt like your PM tool is just a fancy to-do list that doesn't really streamline anything, this conversation will change your perspective. The hosts get real about the five foundational elements that separate teams who struggle with scattered workflows from those who've built AI-powered automation hubs.

In this episode, you'll learn:

• Why standardization comes before automation and the chaos that happens when you skip this step
• How to template everything without losing your mind or creativity
• The tough love truth about where ALL work must live (hint: not in Slack)
• Why collaboration belongs in your PM tool, not scattered across platforms
• The training approach that actually gets teams using features consistently
• Real examples of how AI agents like Perry and Cleo leverage these foundations

If you're ready to transform your project management tool from a glorified to-do list into the command center for seamless workflows and AI automation, this episode shows you exactly how to build those foundations.

If this episode hits home, we have free PM basics courses for ClickUp, Asana, and monday.com at biggestgoal.ai. Share them with your team. They'll thank you.

Upcoming Education Sessions:

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

Tools/Platforms Mentioned

• Project Management Tools: ClickUp, Asana, and monday.com
• Slack
• Microsoft Teams
• Claude Cowork
• n8n
• Perry (Podcast Agent)
• Cleo (Client Onboarding Agent)

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

A hundred episodes ago, Alane Boyd and Micah Johnson asked what if you could save one hour a day... and that felt ambitious. Now they're watching AI compress entire job functions into a single afternoon.

This milestone episode isn't just a celebration, it's a timeline of the AI revolution in business. From traditional automation and project management tools to AI agents that completely transform how companies operate.

In this episode, you'll learn:

• How the AI conversation evolved from "save an hour" to "transform everything" in 24 months
• Why the fundamentals matter more now than ever (good data, workflows, APIs)
• What companies are doing wrong when they try to add AI to old processes
• The timeline that changed everything from ChatGPT to Claude Cowork
• Predictions for the next 100 episodes and where business automation is heading
• What hasn't changed (great judgment, team members) vs what's accelerating

If you've been on this journey or just starting to think about AI in your business, this episode is both your celebration and your roadmap for what's possible.

Upcoming Education Sessions:

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

Tools/Platforms Mentioned

• Claude Cowork
• ChatGPT
• Perplexity
• Automation Platforms: n8n, Zapier, Make
• PM Tools: ClickUp, Asana, Monday
• MCP Servers
• APIs
• Gamma

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!