Coffee Chat Playbook Generator

This skill helps you prepare for professional coffee chats by gathering intelligence on the person and generating personalized conversation guides.

Prerequisites

Before using this skill, set up the following. Only Apify CLI is required for X scraping — everything else is optional.

1. Apify CLI (required for X/Twitter scraping)

Apify CLI is used to run the tweet scraper actor.

Install:

npm install -g apify-cli

Authenticate:

apify login
# Paste your Apify API token when prompted
# Get your token at: https://console.apify.com/account/integrations

Verify:

apify info
# Should show your username and token

Free tier includes $5/month of compute credits. Scraping 10 tweets costs ~$0.004, well within free limits.

2. Notion Integration (optional — for saving playbooks to Notion)

Create an integration:

1. Go to https://www.notion.so/my-integrations
2. Click "New integration"
3. Give it a name (e.g. "Coffee Chat Skill")
4. Copy the Internal Integration Token

Set the API key:

export NOTION_API_KEY="secret_xxxxxxxxxxxxxxxxxxxx"
# Add to your shell profile to persist:
echo 'export NOTION_API_KEY="secret_xxxxxxxxxxxxxxxxxxxx"' >> ~/.zshrc

Share your Notion page with the integration:

1. Open the Notion page where you want playbooks saved
2. Click "..." → "Add connections" → select your integration
3. Copy the page ID from the URL:
   • URL: https://notion.so/My-Page-abc123def456...
   • Page ID: abc123def456... (the part after the last -)

Update NOTION_PAGE_ID in the Notion Push section of this skill.

3. Web Search & Fetch (required for company and background research)

This skill relies on web search and web fetch to research the target's company, industry, and background in Steps 2 & 3. Your AI agent needs access to these tools.

If using OpenClaw or Claude Code:

• Web search and WebFetch are built-in — no setup needed

If using another agent framework, make sure it has access to:

• A search API (e.g. Brave Search, Serper, Tavily, You.com) for querying company news, funding rounds, founder backgrounds
• A web fetch / scrape tool for reading pages (company websites, LinkedIn profiles, news articles)

Without these tools the agent will fall back to training knowledge only, which may be outdated. Research quality will drop significantly.

4. Summary of everything you need

Setup (First Time)

Before using this skill, create your profile file at memory/my-profile.md:

# My Profile

- **Name**: [Your Name]
- **Role**: [Your current role and company]
- **Background**: [Brief career background, e.g. Finance → VC → AI]
- **Location**: [City, Country]
- **LinkedIn**: [Your LinkedIn URL]
- **Interests**: [Topics you care about / want to discuss]

Also configure integrations (optional):

• Notion: Set NOTION_API_KEY env var and update NOTION_PAGE_ID in the Notion Push section below
• Apify: Set APIFY_API_TOKEN env var for LinkedIn scraping (free tier available)

Workflow

Step 1: Collect Information

Ask the user for:

1. Target person's name (required)
2. Target's LinkedIn profile URL (optional but recommended)
3. Target's company name (required for research)
4. Target's X (Twitter) username (optional, e.g. @elonmusk or just elonmusk) — used for scraping recent posts
5. Context of the meeting (optional - how you met, goal)

Load your profile from memory/my-profile.md for comparison.

Step 2: Research Target's Company

For each target, do comprehensive company research:

1. Web search for company info:

   • Funding news
   • Product/feature launches
   • Team / founders

2. X (Twitter) search for company account:

   • Recent posts
   • Product demos
   • Engagement with community

3. News search for recent coverage:

   • Funding announcements
   • Product launches
   • Competitor/industry analysis

Step 3: Research Target's Background

1. Find LinkedIn profile via web search
2. Scrape LinkedIn posts (if available via Apify)
3. Scrape X (Twitter) posts — if user provided an X username, run:

apify call apidojo/tweet-scraper --input '{
  "searchTerms": ["from:USERNAME"],
  "maxTweets": 10,
  "sort": "Latest"
}' --output-dataset --silent

Replace USERNAME with the target's X handle (without @).

• Parse the dataset output and extract: tweet text, date, likes, retweets, replies
• If APIFY_API_TOKEN is not set or scraping fails, fall back to web search for recent X posts
• Skip this step silently if no X username was provided

4. Gather background info:
   • Previous work experience
   • Education
   • Notable projects/achievements
   • Recent posts/topics (from both LinkedIn and X)

Step 4: Generate Comprehensive Playbook

Follow the Full Playbook Template below with ALL sections:

• Target Profile Summary
• Company & Industry Research (detailed)
• Founder Deep Dive (for startup targets)
• Recent Content & Posts
• Profile Comparison
• 8 Questions
• 4 Talking Points
• Communication Tips
• Pre-Chat Checklist

Step 5: Save & Push to Notion (optional)

1. Save locally: memory/coffee-chat-{target-slug}-{YYYY-MM-DD}.md
2. Push to Notion: Append to your configured Notion page (if NOTION_API_KEY is set)

Full Playbook Template

# ☕ Coffee Chat Playbook: [Target Company/Name]

**Date:** [YYYY-MM-DD]
**Status:** Researched

---

## 📋 Target Profile Summary

### Basic Info
- **Target**: [Name] (Founder/CEO/PM at [Company])
- **LinkedIn**: [URL]
- **Location**: [City, Country]
- **Connection**: [How you met]

### Background
- [Previous career/experience]
- [Notable projects or achievements]
- [Education]

### Recent Posts / Topics
- [Topic 1 from LinkedIn/X]
- [Topic 2]
- [Topic 3]

---

## 🏢 Company & Industry Research

### Company Overview
- **Company Name**: [Name]
- **Founded**: [Year]
- **Location**: [HQ location]
- **Funding**: [Amount] ([Investors]) - [Date]
- **Team**: [Size/distribution if known]
- **X/Website**: [Links]

### Product
- [Product description]
- [Key features]
- [Target users]

### Industry Landscape
- **Market**: [Brief description of market]
- **Competitors**: [List key competitors]
- **Trends**: [Industry trends]
- **Challenges**: [Key challenges]
- **Opportunities**: [Opportunities]

### Investors (if applicable)
- **Investor 1**: [Background]
- **Investor 2**: [Background]

---

## 👥 Founder Deep Dive (for startups)

### [Founder 1 Name] ([Title])
- **Background**: [e.g., Documentary filmmaker, Ex-Google, etc.]
- **Work history**: [Notable companies/clients]
- **Notable achievements**: [e.g., Founded X, Award Y]
- **Philosophy/Interests**: [From posts]

### [Founder 2 Name] ([Title])
- [Same structure]

---

## 📱 Recent Content & Posts

### LinkedIn Posts
- [Post 1: topic and key message]
- [Post 2]
- [Post 3]

### X (Twitter) Posts — Last 10
> Scraped via apidojo/tweet-scraper. If X username not provided, use web search results.

| # | Date | Tweet | Likes | RT | Replies |
|---|------|-------|-------|----|---------|
| 1 | [YYYY-MM-DD] | [Full tweet text] | [n] | [n] | [n] |
| 2 | [YYYY-MM-DD] | [Full tweet text] | [n] | [n] | [n] |
| 3 | [YYYY-MM-DD] | [Full tweet text] | [n] | [n] | [n] |
| ... | | | | | |

**Key themes from X posts:**
- [Theme 1: what they talk about most]
- [Theme 2: opinions/stances]
- [Theme 3: recent interests or announcements]

**Engagement pattern**: [High/Medium/Low — what type of content gets most engagement]

---

## 🔍 Profile Comparison (You vs Target)

### Your Profile
- **Role**: [Load from memory/my-profile.md]
- **Background**: [Load from memory/my-profile.md]
- **Location**: [Load from memory/my-profile.md]

### Common Ground
- [Common industry or domain]
- [Similar career transition experience]
- [Shared interests]

### Conversation Starters (Based on Research)
1. "[Based on their product launch] I saw [product] launched - what was the inspiration?"
2. "[Based on their background] As someone who transitioned from [old career] to [new career], what surprised you most?"
3. "[Based on their philosophy] Your focus on [X] resonates with me because..."
4. "[Based on investors] How did you approach raising from [Investor]?"
5. "[Based on team] With your distributed team across [locations], how do you manage collaboration?"

---

## 💬 Questions to Ask (8 total)

### 👤 Personal (3)
1. [Question based on their background - e.g., "What prompted your transition from X to Y?"]
2. [Question based on their location/move - e.g., "What's it like building a US company from [location]?"]
3. [Question based on their interests - e.g., "I saw you worked on [project] - what was that experience like?"]

### 💼 Work-Related (3)
4. [Question about their product - e.g., "How is [Company] different from competitors?"]
5. [Question about challenges - e.g., "What's been the biggest challenge building [Company]?"]
6. [Question about team/culture - e.g., "How do you think about team building as a founder?"]

### 🌐 Industry (2)
7. [Question about industry trends - e.g., "Where do you see the industry heading in 2-3 years?"]
8. [Question about advice - e.g., "What advice would you give to someone in my role?"]

---

## 🗣️ Your Talking Points (4)

1. **Your background**: [Load from memory/my-profile.md]
2. **What you admire**: [Something specific from their profile/posts]
3. **Your work**: [Current role and what you're building]
4. **Curiosity**: [Something specific you want to learn from them]

---

## 🧭 Communication Principles & In-Chat Guide

### ☕ The COFFEE Framework (30-min structure)

Use this as your session blueprint. Every great coffee chat has a shape.

| Time | Phase | What to do |
|------|-------|------------|
| 0–5 min | **C — Connect** | Start human. Share who you are briefly. Ask about them first. |
| 5–10 min | **O — Offer Proof** + **F — Frame** | Optionally show a 60-sec artifact (1-pager, analysis, teardown) that proves you've done homework. Then frame the agenda: *"I have a few questions — happy to go wherever is useful for you too."* |
| 10–25 min | **F — Focused Questions** | Ask 2–3 non-Googleable questions. Listen 70%, talk 30%. Follow their thread. |
| 25–30 min | **E — End on Time** | Start wrapping at min 25. Don't let it run over. |
| Closing | **E — Extend Help** | Before you leave: *"Is there anything I can help with from my end?"* |

> **Litmus test for every question:** If the answer is fully on Google or their LinkedIn, don't ask it. Ask things only *they* can answer.

---

### The Golden Rule: 70/30

> **They talk 70%, you talk 30%.** Your job is to draw them out, not to impress them.

- Ask open-ended questions, then listen fully before responding
- Don't fill silence — let them think
- Put your phone away. Be fully present

---

### 🤝 Nonverbal Signals (Don't Overlook These)

| Signal | What to do |
|--------|-----------|
| Eye contact | Maintain natural eye contact — shows you're engaged |
| Nodding | Nod slowly to signal you're following and interested |
| Smile | Warm, genuine smiles — not forced |
| Body posture | Lean slightly forward, open body language, no crossed arms |
| Hands | Keep visible, use to emphasize points naturally |
| Phone | Face-down or away — checking it kills rapport instantly |

---

### 🎭 Identify Their Networker Persona

Read the room in the first 2-3 minutes. Adjust your style accordingly.

#### 🔵 Practicalist
> Fact-driven, problem-solver, sticks to the point, values time efficiency

**Signs**: Gets straight to business, asks direct questions, gives concise answers

**Your technique**:
- Be clear on your intention upfront ("I'm here to learn about X")
- Skip small talk, lead with substance
- Give them space to respond — don't ramble
- Use data and specifics, not vague observations

**Sample opener**: *"I wanted to connect because [specific reason]. I have a few focused questions — hope that works for you."*

---

#### 🟡 Conversationalist
> Personable, relationship-focused, loves stories, open to tangents

**Signs**: Asks personal questions, shares stories, warm and expressive

**Your technique**:
- Power on small talk — ask about their weekend, their city, their journey
- Match their warmth and storytelling style
- Pay close attention to body language — they're reading yours too
- Let conversations flow naturally, don't over-structure

**Sample opener**: *"I loved your post about [X] — it really resonated with me. How did that come about?"*

---

#### 🔴 Dominator
> Dominates the conversation, tends to be the one asking questions, high-status energy

**Signs**: Asks lots of questions, steers topics, rarely pauses for your input

**Your technique**:
- Listen to their questions — they reveal what they care about
- Be more assertive: when there's a natural pause, jump in with your question
- Use bridging phrases: *"That's a great point — it makes me curious about..."*
- Don't wait to be invited — politely redirect to your agenda

**Sample opener**: *"Before I forget — I actually had a specific question I was hoping to get your take on..."*

---

### 💬 Question Bank (70/30 Principle)

Design questions to keep them talking. Follow up on their answers before moving to the next question.

> **How to use this bank:**
> - Pick 2-3 **Core Questions** per section — these are your main agenda
> - Use **Follow-Up Questions** only if time allows and the topic naturally opens up
> - Use **Transition Phrases** to move between topics without abrupt cuts

---

#### 🔓 Warm-Up (first 5 min — build comfort)

**Core:**
- *"How's your week going? Anything exciting on your plate right now?"*
- *"How did you end up in [city/role]? Was it planned or did it just happen?"*

**Follow-up (if they open up):**
- *"What do you enjoy most about being based in [city]?"*
- *"Was there a specific moment that made you decide to make the move?"*

**Transition into background:** *"That's really interesting — I'd love to hear more about your path to where you are now..."*

---

#### 🧬 Background & Journey (understand their path)

**Core:**
- *"What drew you to [industry/role] originally?"*
- *"What's been the most unexpected part of your journey so far?"*
- *"If you could start all over again, would you change your career path in any way?"* *(UB)*

**Follow-up (if time allows):**
- *"If you could go back and tell your younger self one thing, what would it be?"*
- *"Was there a specific decision that really changed the trajectory of things?"*
- *"How long does it typically take for people to rise to more senior levels in this field?"* *(UB)*

**Transition into work:** *"It sounds like you've built a really intentional path. I'm curious how that shapes how you think about [Company] today..."*

---

#### 🏢 Work & Company (go deeper on what they do)

**Core:**
- *"What does a great day at work look like for you right now?"*
- *"What's the hardest problem [Company] is working through?"*
- *"What parts of your job do you find most challenging — and most enjoyable?"* *(UB)*

**Follow-up (if they go deep):**
- *"How has the team's approach evolved as you've scaled?"*
- *"What's something people on the outside misunderstand about what you're building?"*
- *"How would you describe the culture — what kind of person thrives here?"* *(UB)*
- *"Why do people typically leave this company or field?"* *(UB)*

**Transition into industry:** *"Given everything you're seeing up close at [Company], I'd love your take on where the broader space is going..."*

---

#### 🌐 Industry & Trends (show intellectual curiosity)

**Core:**
- *"Where do you think [industry] is heading in the next 2-3 years?"*
- *"What's a trend you're watching that most people aren't paying attention to yet?"*
- *"What are the biggest challenges facing this industry right now?"* *(MIT)*

**Follow-up (if time allows):**
- *"Who do you think is doing the most interesting work in this space right now?"*
- *"Is there a bet you're making that feels contrarian to the mainstream view?"*
- *"Is the field growing — are there good opportunities for newcomers?"* *(UB)*
- *"What developments on the horizon could affect opportunities in this space?"* *(UB)*

**Transition into closing:** *"This has been really eye-opening — before we wrap up, I wanted to make sure I ask..."*

---

#### 🤝 Relationship-Building & Closing (make it mutual)

**Core:**
- *"Is there anything I can help with from my end — introductions, resources, anything?"*
- *"Would it be okay to keep in touch? I'd love to follow your journey."*
- *"Are there any questions I should have asked but didn't?"* *(MIT — always ask this)*

**Follow-up:**
- *"Who else do you think I should be talking to in this space? Would it be okay to use your name?"* *(UB)*
- *"What resources — books, podcasts, communities — would you recommend I look into?"* *(MIT)*

---

#### ⚡ Persona-Specific Follow-Ups
- **Practicalist**: *"How do you measure success on that?"* / *"What's the ROI you're seeing?"*
- **Conversationalist**: *"Tell me more about that — how did it feel?"* / *"What was the moment you knew?"*
- **Dominator**: *"You mentioned [X] — I've been thinking about that a lot. Can I ask your take on [Y]?"*

---

#### 🏛️ Consulting / Finance / High-Prestige Firm (use when target works at MBB, Big 4, investment bank, etc.)

These questions are sharper and more direct — suited for time-pressed, high-status professionals who respect preparation.

**About their firm & culture:**
- *"What surprised you most about [Firm] that you only discovered after joining?"*
- *"How would you describe someone who truly excels here — what separates them from the rest?"*
- *"What do you see as [Firm]'s biggest opportunity and biggest challenge right now?"*
- *"How would you compare [Firm] to others you've worked with or considered?"*

**About their career path:**
- *"What underrated skill do you think accelerated your growth here?"*
- *"What surprised you most moving from individual contributor to managing others?"*
- *"Looking back, what do you wish you'd known before entering this field?"*

**Situational / behavioral (if they're senior and the vibe allows):**
- *"Tell me about a time you had to persuade someone to change their mind when the stakes were high — how did you approach it?"*
- *"Describe a moment when you had to make a call with limited information. What did you do?"*
- *"What's a professional risk you took that paid off — and one that didn't?"*

**About breaking in (if you're exploring the field):**
- *"How do most people at your level enter this field — what paths tend to work?"*
- *"Considering my background, how well do you think I'd fit into this type of role?"* *(UB)*
- *"What would you recommend I do in the next 6 months to be a stronger candidate?"*
- *"Are there specific companies or teams within the industry you'd suggest I look at?"*

> **Tone note for consulting/finance targets:** Be crisp. Lead with your agenda. They appreciate directness and hate meandering. Show you've done the homework — reference their work, their firm's recent deals or reports, their public writing.

---

### 🔍 Finding Common Ground (TLDR)

Before the chat, scan their LinkedIn/X for:
- **Shared experiences**: same industry, career pivot, city, university
- **Shared interests**: topics they post about repeatedly
- **Shared values**: how they talk about their work and people

Use these to open genuine threads — not forced flattery. One real connection beats five generic questions.

---

### ✨ Value-Added Mindset

Go in with a giving mentality, not just a taking one:
- Bring a relevant article, resource, or intro to offer
- Share a genuine observation about their work: *"I noticed [X] — have you considered [Y]?"*
- Follow up within 24hrs: summarize 1-2 things you learned and mention what you'll do next

---

## ⚠️ Communication Tips

- **Tone**: Warm, curious, show genuine interest in their journey
- **Attitude**: Be authentic, appreciate their unique background
- **Address**: First names
- **Time Zone**: [Check time zone difference if remote]

---

## ✅ Pre-Chat Checklist

- [ ] Review company website and product
- [ ] Check recent LinkedIn/X posts
- [ ] Prepare 30-sec self introduction
- [ ] Set up calendar invite (consider time zones)
- [ ] Have questions ready
- [ ] Have pen and paper for notes

Notion Push (Optional)

Requires NOTION_API_KEY environment variable and your target page ID.

# Set your Notion page ID here
NOTION_PAGE_ID="YOUR_NOTION_PAGE_ID"
NOTION_KEY="${NOTION_API_KEY}"

curl -s -X PATCH "https://api.notion.com/v1/blocks/${NOTION_PAGE_ID}/children" \
  -H "Authorization: Bearer $NOTION_KEY" \
  -H "Notion-Version: 2022-06-28" \
  -H "Content-Type: application/json" \
  -d '{
    "children": [
      {"object": "block", "type": "heading_1", "heading_1": {"rich_text": [{"text": {"content": "☕ Coffee Chat Playbook: [Target]"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "Date: [YYYY-MM-DD]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "📋 Target Profile Summary"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[Basic info, background, recent topics]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "🏢 Company & Industry Research"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[Funding, location, team, product, industry landscape]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "👥 Founder Deep Dive"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[Background, work history, achievements, philosophy]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "📱 Recent Content & Posts"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[LinkedIn posts + X activity]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "🔍 You vs Target"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[Common ground and conversation starters]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "💬 Questions (8)"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[8 questions: 3 personal, 3 work, 2 industry]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "🗣️ Talking Points (4)"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[4 talking points]"}}]}},
      {"object": "block", "type": "divider", "divider": {}},
      {"object": "block", "type": "heading_2", "heading_2": {"rich_text": [{"text": {"content": "⚠️ Tips & ✅ Checklist"}}]}},
      {"object": "block", "type": "paragraph", "paragraph": {"rich_text": [{"text": {"content": "[Communication tips and pre-chat checklist]"}}]}}
    ]
  }'

Quality Standards

1. Always include Company & Industry Research - funding, product, competitors, trends
2. Always include Founder Deep Dive - for startup targets, research each founder's background
3. Always include Recent Content - LinkedIn posts + X activity
4. Always compare profiles - find common ground between you and the target
5. Generate exactly 8 questions - 3 personal, 3 work, 2 industry
6. Generate exactly 4 talking points - show you've done homework
7. Save locally - always save to memory/coffee-chat-{target-slug}-{YYYY-MM-DD}.md
8. Push to Notion - if NOTION_API_KEY is configured
9. Make questions specific - based on their background, posts, company news

Known Limitations

LinkedIn Scraping

• LinkedIn company scrapers often return wrong data
• LinkedIn profile scrapers may fail on free Apify tier
• Workaround: Use web search for company/founder info, check X for recent posts

Profile Cache

• Located at: memory/my-profile.md
• If missing, ask the user to provide their background before proceeding

Notion

• Requires NOTION_API_KEY environment variable
• Set your page ID in the Notion Push section above
• Notion API version: 2022-06-28