A Claude skill that reviews and coaches any document, pitch, email, or message before you share it with a senior leader or executive.
Built on research into how executives actually make decisions — not how we assume they do.
Install this skill and Claude will automatically activate it whenever you're preparing something for a leader. It reviews your content against a structured checklist and gives you specific, honest feedback — not generic encouragement.
It checks for:
- Are you leading with the recommendation, or making them earn it?
- Are you presenting options, or forcing a yes/no?
- Does your pitch connect to what they're measured on — not just what you care about?
- Are you responding to a subtle thread they dropped, and did you make that visible?
- Do you have cross-functional support, or is this just your opinion?
- Have you defined a specific kill date to de-risk the ask?
- Are you going in to learn, or just to get a rubber stamp?
It also simulates exec-specific pushback — if you paste in past feedback or known positions from your specific executive, it red-teams your pitch against their beliefs, not a generic sceptic.
executive-influence-coach/
├── README.md
├── SKILL.md — Main coaching logic and review checklist
├── executive-influence-coach.skill — Packaged skill file (install this)
├── influence_playbook.md — Full playbook distilled from the podcast
├── transcipt_lenny.pdf — Source transcript: Lenny's Podcast with Jessica Fain
└── references/
├── before-the-meeting.md — Research tactics and exec simulation with AI
└── building-trust.md — Shrink the change, kill things, act fast
- Download
executive-influence-coach.skill - In Claude.ai, go to Settings → Skills → Add Skill
- Upload the
.skillfile - Done — Claude will now use it automatically when relevant
Just share what you're about to send or present:
"I'm about to send this strategy doc to my CPO tomorrow — can you review it?"
"I have a product review with my VP on Friday. Here's my pitch deck. Coach me."
"Review this email before I send it to my skip-level."
Claude will ask a few targeted questions (what are the exec's current pressures, any past feedback you can share) and then give structured coaching.
Treat your executive like your most important user.
You apply curiosity and empathy to understand customers. The moment you walk into an exec meeting, most people forget those skills entirely. This skill is a forcing function to remember them.
"It's not your fault — but it is your problem." — Annie Pearl (ex-CPO Calendly, Glassdoor)
The coaching framework in this skill is based on insights from Jessica Fain (product leader at Webflow, former Chief of Staff to the CPO at Slack) as discussed on Lenny's Podcast — "The Art of Influence: The Single Most Important Skill That AI Can't Replace" (March 2026).
The skill was built as a practical implementation of those ideas — something you can actually use the day before a difficult conversation, not just read and forget.
Also worth checking out: User Story Mapping Skill
Built by Tom Shahar. Contributions and feedback welcome.