What does the Ryan skill do?

Ryan prepares board packs, writes all-hands communications, structures decision frameworks, and handles the high-stakes internal communications that flow through the CEO office. Load once into Claude Projects and get a configured Chief of Staff without explaining context at the start of every session.

How do I install this skill file?

Download the .md file, paste the full contents into Claude Projects Instructions, add your business context, and start your first session. Works with Claude, ChatGPT, or any AI chat accepting system prompts.

Which AI tools does this skill work with?

Works with Claude (recommended), ChatGPT, and any AI chat accepting system prompts. Claude Projects gives the best results — the skill is optimised for Claude's instruction-following capabilities.

What is included in this download?

One .md skill file delivered instantly after purchase. Contains the full role configuration, expertise context, and behavioural rules. No subscription required — yours permanently. Works with Claude, ChatGPT, or any AI chat.

How is this different from using Claude without the Ryan skill?

Without a skill file, Claude starts every session as a general-purpose assistant. With Ryan loaded, Claude applies Chief of Staff expertise and methodology from the first message — no re-explaining, consistent quality every time.

Chief of Staff AI Skill for Claude & ChatGPT

Name: Ryan — Chief of Staff AI Skill
Brand: KissMySkills
SKU: chief-of-staff-skill-claude
Price: 39.0 USD
Availability: InStock
Rating: 4.75 (20 reviews)

Ryan — Chief of Staff AI Skill

$39.00

Ryan — Chief of Staff AI Skill

$39.00

⚡ Instant download ◆ Claude & ChatGPT ∞ Keep forever

Instant download · 30-day money-back guarantee. Pay once, keep forever — no subscription. Refund policy

Get chief-of-staff output — board packs, all-hands, OKRs, and briefings — that makes the decision obvious on one page.

One-page briefings and decision memos with a recommendation
Board packs, CEO letters, and investor updates
OKR frameworks and company strategy narratives
DACI/RACI and two-way-door decision structures

CEOs, founders, and execs who need leverage, not a glorified EA.A chief of staff costs $150,000+/yr — this is one file, yours forever.

// what's inside

Drop Ryan into Claude and get a Senior Chief of Staff with 9 years supporting CEOs and C-suite executives — preparing board packs, writing all-hands communications, building OKR frameworks, producing executive briefings, and driving cross-functional initiatives that have no natural owner.

Ryan is not a glorified EA. He owns outcomes. Headline first, always — key message, supporting detail, action. When given a task, Ryan thinks about what the executive actually needs, not just what they asked for. If a brief needs 10 pages, it has failed. The best CoS output makes the decision obvious on one page. Ryan treats all context as confidential.

What you get

→ Executive office documents — one-page briefings for meetings and decisions, action item trackers, weekly executive digests, and decision memos with options and clear recommendations
→ Board and investor materials — board meeting packs, CEO letters, post-board follow-up communications, investor update letters, LP reports, and fundraising narrative frameworks
→ Strategic planning — OKR frameworks, company strategy narratives, vision documents, competitive analysis summaries, leadership offsite agendas, and facilitation plans
→ Internal communications — all-hands presentations, company updates, leadership announcements, sensitive communications (restructures, leadership changes), and weekly OKR progress reports
→ Cross-functional initiative management — project plans and milestone trackers, stakeholder communication frameworks, cross-functional accountability structures, and blocker resolution frameworks
→ Decision-making support — DACI and RACI frameworks, two-way vs one-way door decision structures, leadership meeting agendas built around the decisions that actually need to be made

📄 ryan-chief-of-staff.skill

Under 2 min install

Works with Claude, ChatGPT & any AI chat

How to install

Download the .skill package → open Claude → paste SKILL.md into your Project Instructions or system prompt → describe the executive task, meeting, or communication you need → Ryan produces the output instantly. All context treated as confidential.

ryan-chief-of-staff.md

# Ryan — Chief of Staff AI Skill

You are Ryan, a senior chief of staff. You own outcomes, lead with the headline, and make the decision obvious on one page.

## What you do
- Board packs, CEO communications, OKRs, exec briefings
- Cross-functional initiatives with no natural owner
- Decision memos with options and a recommendation

## How you work
1. Ask what decision or outcome this serves
2. Headline first, supporting detail second
3. If it needs 10 pages, it has failed — compress

Excerpt from the actual file you'll download.

// try it

prompt

$Board meeting is in 6 days and we have no deck. Build me the board-pack outline and the CEO update narrative.

Ryan returns: a board-pack structure (sections, owners, what each must say) → a CEO update written headline-first → the 3 decisions the board actually needs to make → a one-page pre-read so nobody walks in cold.

// how to install Under 2 minutes

Four steps. Any AI chat.

01
Download the file
After checkout, the download link lands in your inbox. Save the file anywhere on your device.
02
Open your AI chat
Claude, ChatGPT, Gemini, Grok, or Copilot — whichever one you already use.
03
Paste the file contents
Drop it into the system prompt, Project instructions, or custom instructions field.
04
Start working
Your AI is now configured as a specialist. Ask it anything inside its domain.