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.

Our workshops align your leadership team on a shared AI roadmap. Our 4-week cohort get your teams building real AI agents, and automation workflows. And our ongoing groups keep leaders and builders sharp long after the cohort wraps.

Upcoming Sessions:

• 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!

For more information, visit our website at biggestgoal.ai.

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.

Our workshops align your leadership team on a shared AI roadmap. Our 4-week cohort get your teams building real AI agents, and automation workflows. And our ongoing groups keep leaders and builders sharp long after the cohort wraps.

Upcoming Sessions:

• 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!

For more information, visit our website at biggestgoal.ai.

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.

Our workshops align your leadership team on a shared AI roadmap. Our 4-week cohort get your teams building real AI agents, and automation workflows. And our ongoing groups keep leaders and builders sharp long after the cohort wraps.

Upcoming Sessions:

• 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!

For more information, visit our website at biggestgoal.ai.