Claude Skills / Caseproof 2026
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Caseproof Team Retreat · 2026

Claude
Skills.

Stop re-explaining yourself.
Paul Carter  ·  Seth Shoultes 45 minutes · workshop
The problem we're solving

Every chat, every time.

— Before skills
  1. 01Open new chat
  2. 02Paste the same three paragraphs of context
  3. 03"Use this format, this tone, these fields…"
  4. 04Next chat — do it all again.
The cost
  • Inconsistent replies to customers
  • Time lost re-explaining
  • New hires ship work that doesn't match standards
— With skills
  1. 01Type your request
  2. 02Skill loads automatically
  3. 03Done. Your way. Every time.
The win
  • Consistent quality from everyone
  • New teammate = same output, day one
  • Your judgment, encoded once, used forever
One line to remember
A Skill is an SOP that Claude reads before it starts the task.
It's your Notion doc for a new hire —
except the new hire is Claude.

Preferences

Shape how Claude talks.

Projects

Give it context.

Skills

Teach it jobs.

How it works · four steps

Upload, prompt, match, done.

Claude doesn't load every skill into every conversation. It only loads what's relevant. That's why dozens of skills work.
01

Upload

Zip your skill folder and upload it.

02

Prompt

You send a message to Claude.

03

Match

Claude scans skill descriptions — loads what fits.

04

Done

Task gets done your way. Every time.

Progressive disclosure

Your code review skill stays asleep when you're writing an email. Your support skill stays asleep when you're drafting a PR. Only the right skill wakes up.

A skill in action

Watch what happens when I type one sentence.

I didn't paste any rules. I didn't explain brand voice, structure, or sign-off. The skill handled all of it, silently.
claude.ai · support
> ▋
[system] scanning skill descriptions…
[match] Support Reply Writer — loaded
[system] applying brand voice, empathy, sign-off

Scan

Claude reads every skill description to find what fits.

Match

Only the right skill loads — in this case, Support Reply Writer.

Apply

Brand voice, empathy rules, sign-off format — all inherited.

Deliver

A personalized, on-brand reply. No rules pasted.

You never see the skill load. It just works.
Three types

Three flavors. One discipline.

Built-in

Anthropic Skills

  • Excel · Word · PowerPoint · PDF
  • Always available
  • This deck was built with one
They just work.
Marketplace

Partner Skills

  • Notion · Figma · Atlassian
  • Pulled from the Skills Directory
  • Pair with MCP connectors
Extend the reach.
You build these

Custom Skills

  • A markdown file — no coding
  • Loads when it's relevant
  • If you can write a Google Doc, you can write a skill
This is where we live today.
Available on every plan · Free · Pro · Max · Team · Enterprise
Failure modes

Good skills. Bad skills.

The four ways skills fail — and the fix for each.
Vague
"Helps with writing tasks." Fires on everything or nothing.
→ Better
"Use when replying to a customer support ticket about billing, payments, or refunds."
Kitchen sink
One skill that does support AND marketing AND dev.
→ Better
One skill. One job. Always.
No examples
Ten rules. Zero samples. Rules alone aren't enough.
→ Better
One good example teaches more than ten rules.
Never tested
Upload and forget. You'll never know if it works.
→ Better
Run three or four prompts. Watch what fires. Tighten.
Real examples · engineering

Dev team skills.

Four candidates that solve problems we actually have.

Code Review Checklist

Bakes in team standards. Security, performance, WordPress coding standards — every review, same checks.

Bug Report Writer

Forces our template: product, steps to reproduce, expected vs. actual, environment. No more "it's broken."

Git Commit Message Writer

Conventional commits, our prefix style, ticket numbers in the right spot.

API Doc Generator

Consistent endpoint documentation generated directly from code.

Pair a skill with Claude Code → automate PR reviews end to end.
Real examples · support

Support team skills.

Where skills compound fastest — because consistency is everything.

Support Reply Writer

Brand voice, empathetic opener, correct sign-off. Every agent sounds like the same company.

Ticket Triage Summarizer

Product, category, severity, suggested assignee. Great for shift handoffs.

Known Issue Responder

References known-issue docs. Drafts the reply with the right workaround already included.

Escalation Writer

Formats escalations so engineering gets exactly the fields they need. No back-and-forth.

On our Team plan → deploy org-wide. Everyone sounds like us.
Real examples · growth & marketing

Growth & marketing skills.

Brand consistency without the bottleneck.

Brand Voice Writer

Tone guide, word list, do-not-use list — embedded. Drop the style guide in the references folder and Claude reads it every time.

Email Campaign Builder

Subject line formula, preview text, CTA placement rules.

SEO Content Brief Writer

Keyword targeting, structure, competitor awareness.

Launch Announcement Drafter

Cross-channel consistency: blog, email, and social all sound like us.

The references/ folder is real → drop your style guide in there.
The compounding win
Skills turn your individual judgment into team-wide consistency.
Support lead's instincts
→
In a skill
Dev lead's standards
→
In a skill
Marketing's voice
→
In a skill
New person joins Monday — same output as someone here three years.
Your turn · find your best idea

Three questions.

01

What do you explain to Claude over and over?

If you're pasting the same paragraph into new chats — that's a skill.

02

What needs to look or sound a specific way?

Templates, formats, voice. Consistency problems are skill problems.

03

What would you write as an SOP for a new hire?

If you'd put it in Notion for a human, Claude can follow the same instructions.

Starter ideas · pick one or bring your own

If nothing's jumping out, start here.

Dev
"Write a PR description for this diff."
Our template, linked ticket, change summary, test steps.
Support
"Reply to this support ticket."
Brand voice, empathy first, specific fix, correct sign-off.
Growth
"Write a launch announcement for [feature]."
Blog tone, key benefits, CTA, cross-channel variants.
Ops / PM
"Summarize this meeting."
Attendees, decisions, action items with owners, follow-up date.
Pick the one that makes you groan when you do it manually.
How to write a skill.md

Two parts. Twelve lines. One job.

my-skill/ SKILL.md references/ ← optional ├── style-guide.md └── templates/
Frontmatter · top of file
--- name: Support Reply Writer description: > Use when replying to a customer support ticket. ---
Body · plain markdown
## Role You are a support agent for Caseproof. ## Rules 1. Start with the customer's name 2. Acknowledge the issue first 3. Offer a specific fix ## Example Input: [what the user types] Output: [what Claude produces]
Pro tip · Don't write this from scratch. Describe your task to Claude and say "create a SKILL.md for this." It drafts, you edit. Use Claude to build your Claude skills.
Try the demo skill · open in Claude  ·  download .skill
Build your skill

15 minutes.

Clock starts when you're ready.
Min 1 – 2

Pick your idea.

One repetitive task from your role. If you're stuck, grab one from the starter ideas.

Min 3 – 10

Write your SKILL.md.

Description (trigger phrases) · at least three rules · one example output.

Min 11 – 15

Share.

What problem are you solving? Read your description line.

15:00
Goal: walk out of this room with one skill you can upload today.
Let's see it work

Twelve lines of markdown.

Claude does the job the way you want.
Every time.
Upload & share · five steps

Get it live in under a minute.

1

Folder

Named after your skill.

2

SKILL.md

Inside the folder (you just wrote this).

3

Zip

Right-click · Compress.

4

Upload

Claude.ai · avatar · Customize · Skills.

5

Test

Run a few prompts. Watch what fires. Iterate.

— Gotcha

Code Execution must be enabled.
Settings → Capabilities

If your skill won't fire, check this first.

— Team plan

An admin can push skills to the whole org.

Once yours is ready — we deploy it to everybody.

One more thing · Caseproof plugin marketplace

Beyond Claude.ai.

Everything we just built — those are skills for Claude.ai. We also have an internal plugin marketplace for Cursor and Claude Code.

DevKit

Point it at a GitHub issue. Full pipeline.
  • Branch, implement, test, commit
  • Open PR, run code review
  • Watch CI, fix failures
+ standalone skills: commit · create-pr · coding-standards · multi-model review

DesignKit

This deck was built with DesignKit.
  • Interviews you about your talk
  • Picks a rhetorical framework
  • ASCII mockups before generating
  • Exports to PowerPoint · Gamma · Canva
Best for: keynotes, retreat sessions, executive briefs.
Build a skill worth sharing beyond Claude.ai? Come find me or Thomas — we'll package it for the marketplace.
One takeaway

Build the skill. Test it. Share the one that works.

I'll be around the rest of the retreat.
Want help polishing yours? Grab me.
docs.anthropic.com/skills · claude.ai/customize Let's go build some skills.

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