Leadership Coach Skill

Help users become better leaders and managers using proven frameworks.

When This Skill Activates

• "How do I give feedback?"
• "Should I micromanage?"
• "My team isn't executing"
• "How do I develop my team?"
• "Driving organizational change"
• "Am I a good manager?"
• "Career advice"
• "Building leadership skills"

Framework Selection Guide

Situation	Use This Framework
Giving difficult feedback	Radical Candor
Deciding how hands-on to be	Selective Micromanagement
Team not executing, need change	Managing Complex Change
Developing team members	Bloom's Taxonomy Coaching
Building leadership legacy	Coaching Tree
Personal career growth	Career Impact Framework

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Framework 1: Radical Candor

Source: Kim Scott - Lenny's Podcast Key Insight: Good feedback requires both caring personally AND challenging directly.

The 2x2 Matrix

	Challenge Directly	Don't Challenge
Care Personally	Radical Candor ✓	Ruinous Empathy
Don't Care	Obnoxious Aggression	Manipulative Insincerity

Radical Candor (Goal)

• Care about the person
• Challenge their work/behavior
• Specific and actionable
• Delivered with respect

Ruinous Empathy (Common Trap)

• Care about person but avoid hard feedback
• "I don't want to hurt their feelings"
• Short-term kindness, long-term harm
• Person never improves

Obnoxious Aggression

• Challenge without caring
• Brutal honesty without empathy
• Creates fear, not growth

Manipulative Insincerity

• Neither care nor challenge
• Political, fake feedback
• Worst of all quadrants

Delivering Radical Candor

Step 1: Establish You Care Build relationship first. Feedback lands better from someone who clearly cares.

Step 2: Be Specific Not: "Your presentations need work" Yes: "In yesterday's presentation, you lost the room when you went into technical details. The executives needed business impact first."

Step 3: Make It Actionable Include what to do differently.

Step 4: Do It Quickly Feedback decays rapidly. Give it within 48 hours.

Step 5: Do It Privately (Usually) Praise publicly, critique privately.

Receiving Feedback

• Thank them for the feedback
• Clarify to understand
• Don't defend immediately
• Reflect, then respond

Pitfalls to Avoid

• Defaulting to Ruinous Empathy
• Feedback without relationship
• Being vague to soften it
• Waiting too long

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Framework 2: Selective Micromanagement

Source: Ravi Mehta - Lenny's Podcast Key Insight: Micromanagement isn't always bad—selective, temporary micromanagement is effective when your team is going in the wrong direction.

The Leadership 2x2

	Team Has Autonomy	Team Lacks Autonomy
You're Confident	Scalable Leadership ✓	Selective Micromanagement ✓
Not Confident	Hands-Off (Risky) ✗	Micro-Mismanagement ✗

Scalable Leadership (Ideal State)

• You're confident in direction
• Team has autonomy
• You've established frameworks
• Team makes good decisions

Selective Micromanagement (When Needed)

• You're NOT confident in direction
• You temporarily reduce autonomy
• You guide to right path
• You pull back when aligned

Hands-Off (Failure Mode)

• You're NOT confident but let them continue
• "I don't want to micromanage"
• Team goes off the rails

Micro-Mismanagement (Failure Mode)

• Constant control
• No clear end in sight
• No autonomy ever
• Everyone frustrated

Assessing Confidence Level

High Confidence:

• Decisions align with strategy
• They anticipate your concerns
• Work product meets bar
• You'd make similar choices

Low Confidence:

• Decisions seem off-strategy
• Surprised by their direction
• Quality issues emerging
• You'd make different choices

Executing Selective Micromanagement

Step 1: Be Transparent

"I noticed [concern]. I'm going to be more hands-on for a few weeks to help us get aligned."

Step 2: Get Tactical Get into specific decisions, not just strategy

Step 3: Teach Frameworks Share how you think, not just what to do

Step 4: Plan the Exit

• Define what "aligned" looks like
• Typically 2-6 weeks, not quarters
• Move from directing to reviewing

Pitfalls to Avoid

• Avoiding micromanagement when needed
• Micromanaging without teaching
• Not having an exit plan
• Micromanaging when you're already confident

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Framework 3: Managing Complex Change

Source: Bangaly Kaba - Lenny's Podcast Key Insight: Missing any single component produces a predictable failure mode.

The Five Components

Component	Purpose
Vision	Where we're going
Skills	Capabilities to execute
Incentives	Motivation to do it
Resources	People, budget, tools
Action Plan	Clear next steps

Missing Component → Failure Mode

Missing	Result
Vision	Confusion
Skills	Anxiety
Incentives	Resistance
Resources	Frustration
Action Plan	False starts

Diagnostic Process

Step 1: Observe the Team

• Sit in meetings, listen
• Talk to people across functions
• Note repeated conversations

Step 2: Match Symptoms to Missing Component

Confusion (Missing Vision):

• "What are we trying to do?"
• People pulling different directions

Anxiety (Missing Skills):

• "I don't know how to do this"
• Quality issues, avoidance

Resistance (Missing Incentives):

• "Why should I care?"
• Passive agreement, no follow-through

Frustration (Missing Resources):

• "We don't have what we need"
• Constant firefighting

False Starts (Missing Action Plan):

• "We keep starting but not finishing"
• Same discussions repeated

Step 3: Address the Right Component

Ease of change (easier → harder):

1. Action Plan (quick tactical wins)
2. Resources (if you have authority)
3. Incentives (needs org support)
4. Skills (takes time)
5. Vision (hardest but most fundamental)

Pitfalls to Avoid

• Jumping to solutions without diagnosis
• Addressing only easy components
• Trying to fix everything at once
• Ignoring resistance (incentives)

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Framework 4: Bloom's Taxonomy for Coaching

Source: Bangaly Kaba - Lenny's Podcast Key Insight: Identify where in the learning progression someone is stuck, then provide appropriate support.

The Six Levels (Basic → Advanced)

Level	Description	Diagnostic
Knowledge	Can recall facts/concepts	"Tell me about X"
Comprehension	Can explain in own words	"Why does X work?"
Application	Can use in specific situation	"How have you used X?"
Analysis	Can apply across contexts	"When would you use X vs Y?"
Synthesis	Can create new approaches	"How would you adapt X?"
Evaluation	Can judge when to use what	"When should we NOT use X?"

Matching Development to Level

Knowledge Gap → Reading, videos, definitions Comprehension Gap → Discussion, teach-back exercises Application Gap → Supervised practice, examples Analysis Gap → Multiple contexts, case studies Synthesis Gap → Novel problems, design exercises Evaluation Gap → Critique exercises, judgment calls

Manager Requirements by Level

• ICs should reach Application for their scope
• Managers must reach Analysis across their teams
• Directors+ need Synthesis and Evaluation

Pitfalls to Avoid

• Teaching at wrong level
• Expecting immediate jumps
• Only developing to Application
• Not checking for progression

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Framework 5: Coaching Tree Leadership

Source: Bangaly Kaba - Lenny's Podcast Key Insight: Your legacy is measured by who you developed, not what you shipped.

What is a Coaching Tree?

In basketball, the coaches who learned under you and went on to success. Same applies to product/tech leadership.

Your Tree Includes

• Direct reports who became leaders
• PMs who grew into senior roles
• Engineers who became managers
• People who say you changed their career

PM as Team Sport

• You're the coach, not the star player
• Success comes from team performance
• Not everyone needs to be LeBron
• Role players matter

Building Your Tree

Step 1: Know People by Name and Story

• Professional background and aspirations
• Personal life and what matters
• Strengths and growth areas
• Motivations and fears

Step 2: Identify Role Types

Role	Value
Star player	High-impact work
Reliable executor	Consistent delivery
Culture carrier	Maintains norms
Domain expert	Deep knowledge
Connector	Cross-team relationships

Step 3: Coach Up, Not Out

• Diagnose where they're stuck
• Provide targeted development
• Give stretch opportunities
• Celebrate progress

Step 4: Delegate for Growth

• Delegation is a gift of growth
• Provide support proportional to stretch
• Expect mistakes, use for learning

Step 5: Stay Connected

• Keep relationships after people move
• Celebrate their wins
• Track where they went

Pitfalls to Avoid

• Being the hero (doing all hard work yourself)
• Only developing stars
• Not staying connected
• Measuring only your direct output

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Framework 6: Career Impact Framework

Source: Bangaly Kaba - Lenny's Podcast Key Insight: Impact = Environment × Skills. Both must be strong.

The Formula

Impact = Environment × Skills

Great skills in bad environment = limited impact Great environment with skill gaps = limited impact

Environment Variables (Score 0-2)

1. Manager (Most important) - Quality and support
2. Resources - Team, budget, tools
3. Scope - Size and importance of remit
4. Team - Skills and dynamics
5. Compensation - Fair and motivating
6. Culture - Supportive environment

Skill Variables (Score 0-2)

1. Communication (Most important) - Written, verbal, listening
2. Influence - Building alignment without authority
3. Strategic Thinking - Connecting to business outcomes
4. Execution - Getting things done

Assessment Process

Step 1: Score Environment Rate each variable, identify low scores

Step 2: Score Skills Rate each, get manager/peer input

Step 3: Identify Limiting Factors Which scores are below 1.0?

Step 4: Assess Changeability Can you change it? How?

Step 5: Decide: Fix or Leave

• Stay if: Low scores changeable, manager supportive
• Leave if: Manager is the problem, multiple unfixable factors

Key Insight on Manager

"People don't leave jobs, they leave managers—because the manager has power to fix many variables."

Pitfalls to Avoid

• Blaming only environment (skills matter too)
• Blaming only yourself (environment matters)
• Not talking to manager
• Optimizing only for compensation

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How to Apply This Skill

1. Identify the leadership challenge

   • Feedback → Radical Candor
   • Team off-track → Selective Micromanagement
   • Change needed → Managing Complex Change
   • Developing someone → Bloom's Taxonomy
   • Leadership growth → Coaching Tree / Career Impact

2. Walk through the relevant framework

3. Help create specific action plan

4. Check in on progress

Related Skills

• /pm-coach - For PM-specific development
• /decision-maker - For leadership decisions
• /hiring-guide - For building teams

Full SOPs (Deep Dives)

Core Leadership

• Radical Candor
• Selective Micromanagement
• Managing Complex Change
• Bloom's Taxonomy Coaching
• Coaching Tree
• Career Impact

Founder & Executive

• Founder Mode
• Company Operating System
• Personal Operating Principles
• 100-Year Thinking
• Technical Founder Leadership
• Trust-Based Culture
• Beginner's Mind

Emotional Intelligence

• Fear/Anger Decision
• Energy Audit
• Creative vs Reactive Leadership

Difficult Conversations

• Compassionate Firing
• Large-Scale Layoffs

Culture Building

• Culture Code Creation
• Culture as Product

Engineering Leadership

• Engineering Management Ladder
• Manager to Manager-of-Managers
• Skip-Level Meetings
• Platform Teams
• Staff Engineer Sponsorship
• Engineering Strategy
• EM-PM Partnership

Career Development

• Career as Product
• 30-60-90 Onboarding
• Executive Coaching
• Introverts Workplace Success

Personal Development

• Radical Self-Inquiry
• Leadership Authenticity
• GENIE Goal Setting
• Overcoming Imposter Syndrome