Lenny Playbooks

Lenny Playbooks - Role-Based Skill Combinations

Curated collections of Lenny skills for specific roles and career stages. Each playbook combines essential skills from the base Lenny skill categories.

Available Playbooks

1. Startup Founder Playbook

For: First-time founders, early-stage startup leaders Stage: Pre-seed to Series A

Core Skills (from lenny- categories):*

• lenny-startup: Fundraising Strategy, Startup Pivoting, Designing Team Rituals
• lenny-hiring: Writing Job Descriptions, Conducting Interviews, Building Team Culture
• lenny-strategy: Defining Product Vision, Writing North Star Metrics, Prioritizing Roadmap
• lenny-growth: Measuring Product-Market Fit, Designing Growth Loops
• lenny-sales: Founder Sales
• lenny-execution: Shipping Products, Managing Timelines

Key Focus Areas:

1. Find product-market fit before scaling
2. Build the founding team
3. Raise capital strategically
4. Ship fast and iterate

2. First-Time Manager Playbook

For: Individual contributors transitioning to management Stage: First management role

Core Skills:

• lenny-hiring: Running Effective 1:1s, Having Difficult Conversations, Delegating Work
• lenny-communication: Written Communication, Stakeholder Alignment
• lenny-decision: Running Effective Meetings, Post-mortems & Retrospectives
• lenny-career: Managing Imposter Syndrome
• lenny-advanced: Coaching Product Managers, Energy Management

Key Focus Areas:

1. Shift from doing to enabling
2. Build trust through 1:1s
3. Learn to delegate effectively
4. Develop your management style

3. Product Manager Playbook

For: PMs at any level Stage: All career stages

Core Skills:

• lenny-strategy: Writing PRDs, Problem Definition, Scoping & Cutting, Setting OKRs & Goals
• lenny-research: Conducting User Interviews, Usability Testing, Analyzing User Feedback
• lenny-execution: Shipping Products, Cross-functional Collaboration
• lenny-communication: Giving Presentations, Stakeholder Alignment
• lenny-advanced: Developing Product Taste, Systems Thinking

Key Focus Areas:

1. Define problems worth solving
2. Understand users deeply
3. Ship with quality and speed
4. Influence without authority

4. Growth Leader Playbook

For: Growth PMs, Growth marketers, Growth leads Stage: Post-PMF companies

Core Skills:

• lenny-growth: Measuring Product-Market Fit, Designing Growth Loops, Retention & Engagement, Pricing Strategy
• lenny-research: Designing Surveys, Analyzing User Feedback
• lenny-marketing: Launch Marketing, Content Marketing, Community Building
• lenny-advanced: User Onboarding, Behavioral Product Design
• lenny-technology: AI Product Strategy

Key Focus Areas:

1. Build sustainable growth loops
2. Optimize activation and retention
3. Experiment systematically
4. Scale what works

5. Engineering Manager Playbook

For: Tech leads becoming managers, Engineering managers Stage: First EM role or scaling teams

Core Skills:

• lenny-hiring: Conducting Interviews, Evaluating Candidates, Onboarding New Hires
• lenny-design: Engineering Culture, Platform & Infrastructure, Design Systems
• lenny-technology: Technical Roadmaps, Managing Tech Debt
• lenny-decision: Running Decision Processes, Evaluating Trade-offs
• lenny-communication: Running Offsites

Key Focus Areas:

1. Build high-performing engineering teams
2. Balance technical debt and features
3. Create strong engineering culture
4. Develop technical leaders

6. Sales Leader Playbook

For: Sales managers, VP Sales, CROs Stage: Building or scaling sales teams

Core Skills:

• lenny-sales: Founder Sales, Building Sales Team, Enterprise Sales, Partnership & BD
• lenny-startup: Sales Compensation Design, Sales Qualification
• lenny-hiring: Writing Job Descriptions, Conducting Interviews
• lenny-communication: Giving Presentations, Stakeholder Alignment
• lenny-strategy: Competitive Analysis

Key Focus Areas:

1. Build repeatable sales processes
2. Hire and develop sales talent
3. Design effective compensation
4. Scale enterprise sales

7. AI Builder Playbook

For: AI/ML PMs, AI engineers, AI startup founders Stage: Building AI-first products

Core Skills:

• lenny-technology: AI Product Strategy, Building with LLMs, AI Evaluation (Evals), Evaluating New Technology
• lenny-strategy: Writing PRDs, Problem Definition
• lenny-research: Conducting User Interviews, Usability Testing
• lenny-advanced: Vibe Coding, Dogfooding
• lenny-growth: Measuring Product-Market Fit

Key Focus Areas:

1. Design for AI's strengths and weaknesses
2. Build robust evaluation frameworks
3. Ship AI products users love
4. Stay ahead of rapid capability changes

8. Executive Communication Playbook

For: Directors, VPs, C-suite executives Stage: Senior leadership roles

Core Skills:

• lenny-communication: Giving Presentations, Written Communication, Stakeholder Alignment, Running Offsites, Media Relations
• lenny-decision: Running Decision Processes, Planning Under Uncertainty
• lenny-hiring: Managing Up, Building a Promotion Case
• lenny-marketing: Brand Storytelling, Positioning & Messaging

Key Focus Areas:

1. Communicate with clarity and impact
2. Align stakeholders at scale
3. Build executive presence
4. Navigate organizational politics

9. Career Growth Playbook

For: Anyone looking to advance their career Stage: All career stages

Core Skills:

• lenny-career: Startup Ideation, Managing Imposter Syndrome, Personal Productivity, Organizational Transformation
• lenny-hiring: Building a Promotion Case, Negotiating Offers, Finding Mentors & Sponsors, Career Transitions
• lenny-advanced: Energy Management
• lenny-communication: Written Communication, Giving Presentations

Key Focus Areas:

1. Build skills before you need them
2. Create visibility for your work
3. Find mentors and sponsors
4. Navigate career transitions

How to Use Playbooks

Quick Start

Ask me to help with a specific playbook:

• "Use the Startup Founder playbook to help me with fundraising"
• "Apply the PM playbook to write a PRD for [feature]"
• "Use the First-Time Manager playbook for my first 1:1"

Combining Skills

Playbooks automatically combine relevant skills. For example:

• "I'm a founder preparing for Series A" → Combines startup, hiring, strategy, and communication skills
• "I'm a new PM at a growth-stage company" → Combines PM, growth, and execution skills

Custom Playbooks

You can request custom combinations:

• "Create a playbook for a technical PM at an AI startup"
• "What skills do I need as a PM transitioning to founder?"

Skill Dependencies

lenny-playbooks
├── lenny-hiring (13 skills)
├── lenny-strategy (10 skills)
├── lenny-growth (4 skills)
├── lenny-research (4 skills)
├── lenny-marketing (5 skills)
├── lenny-sales (4 skills)
├── lenny-communication (5 skills)
├── lenny-decision (5 skills)
├── lenny-execution (3 skills)
├── lenny-technology (6 skills)
├── lenny-design (5 skills)
├── lenny-advanced (12 skills)
├── lenny-career (5 skills)
└── lenny-startup (5 skills)

Source

Lenny's Podcast Playbooks | Lenny's Podcast