How I'm Using Claude Skills to Stop Switching Between Projects
Stakeholder writing coaching, powered by Wes Kao's frameworks, now triggers automatically when I need them most.
For months, I faced this impossible choice: get sharp writing feedback from the frameworks I trusted, or maintain deep project context. I couldn’t have both. Until Claude Skills changed everything.
The frameworks I was trying to use? Wes Kao’s communication coaching, gold for for product leaders (actually, for anyone who manages stakeholders). They can help transform rambling updates into executive-ready communication: leading with decisions needed rather than burying them in paragraph three, structuring information so stakeholders can act immediately. The difference between “thanks for the update” and “approved, let’s move forward.”
The productivity tax I was paying
This was my Frankenstein Claude setup:
Separate Projects for each client, loaded with their strategy docs, product context, and past decisions
One Project dedicated to Wes Kao’s Communication Coaching, built from Lenny’s Podcast transcript and her other Substack articles
But here’s what using them actually looked like:
Step 1: Draft a status update in Client X’s Project. Ask Claude for feedback to make sure I haven’t missed critical points. Claude catches gaps because it knows the client’s context.
Step 2: Copy that message. Open a new thread in the Wes Kao Coaching Project. Paste. Work through the communication structure to make it land properly.
Exhausting, right? And I did this multiple times per day. And honestly? I skipped Step 2 about half the time. The friction was too high, so I’d send “good enough” messages and miss out on Wes’ coaching.
Last week, Claude Skills eliminated that choice. If you’ve ever copied and pasted between tools to get different types of feedback or maintained separate workspaces for different expertise, this can change your workflow, too.
The moment everything changed
On October 16th, Anthropic launched Agent Skills, plug-in modules that help Claude perform focused, repeatable tasks.
A Claude Skill isn’t some mysterious AI construct. It’s just a folder containing a SKILL.md file (your instructions) plus any supporting files you want to reference. To use it in the web app or Claude Desktop, you zip that folder and upload it. That’s it. The whole process took maybe 15-20 minutes, and now it works across every project.
I saw the announcement and immediately knew: Wes’ Coaching is my first Claude skill I’ll build and use.
How I built it
1. I asked Claude to create the skill for me
Claude has a built-in meta-skill (a skill-creator skill) that helps you build new skills. I didn’t need to find or enable anything special—it’s already loaded and ready.
I opened a new chat and said, “Please help me create a new skill that helps me improve my writing to stakeholders based on Wes Kao’s frameworks. Attached are the files with her frameworks.”
I used the same files I’d been using in my dedicated Wes Kao Project, no extra work required - download them here.
2. Claude asked clarifying questions
It wanted to understand my writing style and context, so it asked for writing samples. A few back-and-forth exchanges to get the details right.
3. A few minutes later: the skill was ready
Claude generated a zip file containing the complete skill. It even gave me immediate feedback on a sample message (nice touch, it showed me that Claude made good use of the frameworks).
4. I uploaded it to Claude
Went to Settings → Capabilities → Skills, uploaded the zip file, and it was instantly available across all my projects.
That’s it.
What’s inside a SKILL.md file
The metadata at the top (between the --- lines) tells Claude when to invoke the skill. Everything below is the actual prompt, the frameworks, examples, and instructions Claude should follow.
This is only a sample, download it here to see the whole SKILL.md file
---
name: stakeholder-comms
description: This skill applies Wes Kao’s communication frameworks to improve stakeholder writing. Use when the user needs to write or refine emails, memos, status updates, proposals, or any professional communication to stakeholders (managers, executives, clients, cross-functional partners). This skill provides direct, blunt feedback on what’s wrong and how to fix it using proven frameworks for concision, executive presence, and strategic communication.
---
# Wes Kao Stakeholder Writing Skill
This skill transforms wordy, unclear, or weak stakeholder communication into sharp, executive-ready writing using Wes Kao’s proven frameworks. It provides direct feedback without sugarcoating.
## When to Use This Skill
Use this skill when the user is:
- Writing emails, memos, or messages to stakeholders (managers, executives, clients, partners)
- Asking for feedback on draft communication
- Struggling with being too wordy or unclear
- Needing to sharpen their executive presence in writing
- Wanting to learn Wes Kao’s frameworks through practical application
- Revising communication that didn’t get the desired response
[To see the full prompt, download it]
What changed
Now, when I’m writing stakeholder messages in ANY project, Client X’s product strategy or Client Y’s roadmap, the stakeholder-comms skill triggers automatically. Claude has the tool, knows when to use it, and applies it in the right context.
I don’t even need to say “use the stakeholder-comms skill.” When I start drafting a client update, Claude detects it’s stakeholder communication and automatically applies Wes’ frameworks. This happens 100% of the time, compared to 40-50% when I remembered to use the dedicated project.
The iteration that mattered
Here’s what I learned: The description in your skill’s metadata is how Claude decides when to trigger it. When Claude initially named my skill ‘wes-kao-stakeholder-writing,’ it didn’t trigger consistently. Once I renamed it to ‘stakeholder-comms’ (matching how I naturally talk about the task) and updated the metadata in SKILL.md to match, triggering improved dramatically.
What you should try
What I recommend: Start with Option 2, create your own custom version. Here’s why: Claude will tailor the skill to your specific writing style and needs, making it trigger more reliably than using mine (Option 1).
Option 1
Download my stakeholder-comms skill here, install it and start using it immediately.
Option 2
Choose the frameworks that suit you
Open a new Claude chat
Say: “Help me create a skill to improve my writing comms to my stakeholders based on Wes Kao’s frameworks”
Attach the frameworks
Answer Claude’s clarifying questions about your style and needs
Download the generated skill zip file
Upload to Settings → Capabilities → Skills
Test it in your next relevant conversation
Option 3
Create your own skill.
What repetitive task in your workflow could benefit from a Claude Skill? The best candidates are things you do weekly that follow a consistent pattern or framework. I’m curious about your use cases, I would love to learn more about them. Just leave a comment.
Let’s tinker. Together.
Ady,
Tinkerer in Residence