Month 5: Psychological Safety
Related Phases
Fifth Month Detailed Schedule
Weeks 17-20: Phase 2B - Psychological Safety & Trust
Phase 2A taught you what motivates people. Phase 2B reveals the ENVIRONMENT they need to actually perform - one where they feel safe to take risks, speak up, and bring their full selves to work.
How to Use This Schedule
Daily Time Commitment: 30-60 minutes
- Morning option: During baby’s first nap
- Evening option: After baby’s bedtime
- Split option: 15 min morning + 15-30 min evening
Flexibility Rules:
- Miss a day? Just continue where you left off
- Behind schedule? Skip optional items (marked with *)
- Ahead? Move to next day or go deeper on current material
Icons:
- :movie_camera: Video/Course
- :books: Reading
- :headphones: Audiobook-friendly
- :memo: Writing/Reflection
- :wrench: Setup task
- :brain: AI practice
- :zap: Quick task (< 15 min)
Week 17: The Fearless Organization - Creating Psychological Safety
Goal: Complete “The Fearless Organization” + Assess your own environment’s safety level
Day 113 (Monday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Fearless Organization” - Introduction + Chapter 1 | 45 min |
| :memo: | Note: What is psychological safety? | 10 min |
Key Definition:
“Psychological safety is a belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes.” - Amy Edmondson
Why It Matters: Google’s Project Aristotle found psychological safety was the #1 predictor of team success. Not talent, not resources - SAFETY.
Day 114 (Tuesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Fearless Organization” - Chapters 2-3 | 50 min |
| :zap: | Create 5 flashcards on psychological safety concepts | 10 min |
The Fear-Safety Spectrum:
FEAR <─────────────────────────> SAFETY
Silence <─> Voice
Blame <─> Learning
Self-protection <─> Collaboration
Playing it safe <─> Innovation
Why Teams Fail Under Fear:
- Smart people stay silent
- Obvious problems go unreported
- Bad ideas don’t get challenged
- Good ideas don’t get shared
Day 115 (Wednesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Fearless Organization” - Chapters 4-5 | 50 min |
| :zap: | Watch: Amy Edmondson TED Talk | 12 min |
TED Talk: How to Turn a Group of Strangers into a Team (Amy Edmondson on teaming and psychological safety)
What Psychological Safety IS and ISN’T:
| IS | ISN’T |
|---|---|
| Candor | Niceness |
| Permission to be direct | Permission to be comfortable |
| A climate of openness | A climate of agreement |
| Feeling safe to take risks | Feeling safe from accountability |
Day 116 (Thursday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Fearless Organization” - Chapters 6-7 | 50 min |
| :memo: | Self-Assessment: How safe is your environment? | 15 min |
Team Safety Assessment: Rate your current environment 1-10 on each:
- I can ask questions without looking stupid: ___
- I can admit mistakes without being blamed: ___
- I can challenge ideas without being seen as negative: ___
- I can propose new ideas without being dismissed: ___
- I can ask for help without being seen as weak: ___
Your total: ___ /50
Day 117 (Friday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Fearless Organization” - Chapters 8-9 | 50 min |
| :memo: | Note: The Leader’s Role in creating safety | 10 min |
The Leader’s Role:
- Frame the Work - Set expectations for uncertainty and interdependence
- Invite Participation - Ask questions, genuinely seek input
- Respond Productively - Thank people for speaking up, even with bad news
Questions Leaders Should Ask:
- “What am I missing?”
- “What could go wrong?”
- “Who disagrees with this?”
- “What do you need from me?”
Day 118 (Saturday) - Lighter Day
| Time | Activity | Duration |
|---|---|---|
| :headphones: | Complete “The Fearless Organization” | 45 min |
| :memo: | Action plan: 3 things to increase safety | 15 min |
Case Studies in the Book:
- Pixar: Braintrust meetings with radical candor
- Toyota: Andon cord - anyone can stop production
- Google: Project Aristotle findings
Your Action Plan: Write 3 specific things you can do to increase psychological safety:
Day 119 (Sunday) - Review + Transition
| Time | Activity | Duration |
|---|---|---|
| :memo: | Review all flashcards (Phases 1-2A + new) | 15 min |
| :wrench: | Order/download “Right Kind of Wrong” | 5 min |
| :brain: | AI-assisted safety diagnosis | 20 min |
AI prompt:
Help me diagnose psychological safety in my environment.
I'll describe a recent situation where I (or someone) hesitated to speak up.
Ask me questions to uncover what barriers existed.
Then suggest what could have made it safer.
Week 17 Checkpoint
Before moving to Week 18, you should have:
- Finished “The Fearless Organization”
- Watched Amy Edmondson TED Talk
- Completed Team Safety Assessment (self-rated)
- Written 3 actions to increase safety
- Created 10+ flashcards on psychological safety
- Obtained “Right Kind of Wrong”
Key Insight: Without safety, people can’t access autonomy, pursue mastery, or connect to purpose.
Week 18: Right Kind of Wrong - The Science of Failing Well
Goal: Complete “Right Kind of Wrong” + Learn to distinguish failure types
Day 120 (Monday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Right Kind of Wrong” - Introduction + Chapters 1-2 | 50 min |
| :memo: | Note: Why all failures are not equal | 10 min |
The Core Insight:
Not all failures are equal. We need to distinguish between good failures (intelligent) and bad failures (preventable) - and embrace the right kind.
Day 121 (Tuesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Right Kind of Wrong” - Chapters 3-4 | 50 min |
| :zap: | Create 5 flashcards on failure types | 10 min |
Three Types of Failure:
| Type | Cause | Example | Response |
|---|---|---|---|
| Basic Failures | Inattention, lack of skill | Typo, missed deadline | Prevent with checklists, training |
| Complex Failures | Multiple factors, bad luck | System crash, project failure | Analyze, learn, don’t blame |
| Intelligent Failures | Testing new hypotheses | Experiment that didn’t work | Celebrate! This is innovation |
Day 122 (Wednesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Right Kind of Wrong” - Chapters 5-6 | 50 min |
| :memo: | Failure Audit: Categorize your recent failures | 15 min |
Failure Audit Exercise: Think of 3 recent failures (yours or observed):
| Failure | Type (Basic/Complex/Intelligent) | What was learned? |
|---|---|---|
| 1. | ||
| 2. | ||
| 3. |
Day 123 (Thursday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Right Kind of Wrong” - Chapters 7-8 | 50 min |
| :brain: | AI-assisted failure analysis | 15 min |
AI prompt:
I want to analyze a failure I experienced: [describe the failure].
Ask me questions to help determine:
1. What type of failure was it (Basic, Complex, or Intelligent)?
2. What could have prevented it (if preventable)?
3. What was learned that couldn't have been learned any other way?
The Failure Paradox:
- Organizations that punish all failure get LESS learning
- Organizations that embrace intelligent failure get MORE innovation
- The goal is to fail SMALL and FAST in service of learning
Day 124 (Friday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Right Kind of Wrong” - Chapters 9-10 | 50 min |
| :memo: | Note: How to create a “failure-safe zone” | 10 min |
How to Fail Well:
- Set learning goals - Not just performance goals
- Create a failure-safe zone - Explicit permission to experiment
- Analyze failures - Blameless post-mortems
- Share failures - Make learning public
Questions to Ask After Failure:
- Was this an intelligent failure (hypothesis-testing)?
- What did we learn?
- How can we fail smaller next time?
- Who else should know this?
Day 125 (Saturday) - Lighter Day
| Time | Activity | Duration |
|---|---|---|
| :headphones: | Complete “Right Kind of Wrong” | 50 min |
| :zap: | Watch: Margaret Heffernan TED Talk | 16 min |
TED Talk: Why It’s Time to Forget the Pecking Order at Work
Key insight from Heffernan: Super-chickens (the highest performers) often suppress the performance of others. Teams succeed through social cohesion, not individual stars.
Day 126 (Sunday) - Review + Transition
| Time | Activity | Duration |
|---|---|---|
| :memo: | Review all flashcards | 15 min |
| :wrench: | Order/download “The Culture Code” | 5 min |
| :memo: | Reflection: Your relationship with failure | 20 min |
Reflection Questions:
- How do you typically respond when you fail? _______________
- Do you distinguish between failure types? _______________
- What would change if you celebrated intelligent failures? _______________
Week 18 Checkpoint
Before moving to Week 19, you should have:
- Finished “Right Kind of Wrong”
- Watched Margaret Heffernan TED Talk
- Completed Failure Audit (3 failures categorized)
- Created 15+ flashcards (cumulative for Phase 2B)
- Obtained “The Culture Code”
Research Finding: Organizations with “psychological safety for failure” have 2x the innovation output.
Week 19: The Culture Code - The Secrets of Highly Successful Groups
Goal: Complete “The Culture Code” + Identify belonging cues you can use
Day 127 (Monday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Culture Code” - Introduction + Skill 1 (Build Safety) | 50 min |
| :memo: | Note: What are belonging cues? | 10 min |
The Core Idea: Great cultures aren’t accidents. They’re built through specific behaviors repeated consistently.
Skill 1: Build Safety
- Belonging cues: signals that we’re connected
- Eye contact, physical proximity, attention
- Small moments matter more than big gestures
Day 128 (Tuesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Culture Code” - Skill 1 continued | 50 min |
| :zap: | Create 5 flashcards on belonging cues | 10 min |
Safety Cues to Practice:
- “We’re in this together”
- “Your voice matters”
- “It’s safe to take risks here”
Physical Cues That Signal Safety:
- Leaning in when others speak
- Making eye contact
- Putting away phones
- Nodding and acknowledging
Day 129 (Wednesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Culture Code” - Skill 2 (Share Vulnerability) | 50 min |
| :memo: | Reflection: When have you been vulnerable first? | 15 min |
Skill 2: Share Vulnerability
- Leaders go first
- Vulnerability loops: Person A shares → Person B shares → Trust builds
- “I need help” is strength, not weakness
The Vulnerability Loop:
Leader admits mistake/uncertainty
↓
Team member feels safe to admit theirs
↓
Trust deepens
↓
More vulnerability shared
↓
Even deeper trust
Day 130 (Thursday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Culture Code” - Skill 3 (Establish Purpose) | 50 min |
| :zap: | Watch: Simon Sinek TED Talk | 12 min |
TED Talk: Why Good Leaders Make You Feel Safe
Skill 3: Establish Purpose
- Simple, clear, repeated
- Stories that illustrate “why we’re here”
- Connect daily work to meaningful goals
Day 131 (Friday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Culture Code” - Final chapters + Case Studies | 50 min |
| :wrench: | Order/download “Radical Candor” | 5 min |
| :memo: | List 5 belonging cues you can use | 10 min |
Case Studies in the Book:
- U.S. Navy SEALs
- Pixar Animation
- San Antonio Spurs
- IDEO Design
Your Belonging Cues Action List: Write 5 specific belonging cues you will practice:
Day 132 (Saturday) - Lighter Day
| Time | Activity | Duration |
|---|---|---|
| :headphones: | Complete “The Culture Code” | 40 min |
| :books: | “Radical Candor” - Introduction | 30 min |
Begin “Radical Candor”:
The best managers Care Personally AND Challenge Directly at the same time.
Day 133 (Sunday) - Review + Continue
| Time | Activity | Duration |
|---|---|---|
| :memo: | Review all flashcards | 15 min |
| :books: | “Radical Candor” - Part 1, Chapters 1-2 | 45 min |
The 3 Skills Review:
- Build Safety - Belonging cues
- Share Vulnerability - Leaders go first
- Establish Purpose - Simple, clear, repeated
Week 19 Checkpoint
Before moving to Week 20, you should have:
- Finished “The Culture Code”
- Watched Simon Sinek TED Talk (Why Good Leaders Make You Feel Safe)
- Listed 5 belonging cues you will practice
- Started “Radical Candor”
- Created 20+ flashcards (cumulative for Phase 2B)
Week 20: Radical Candor + Five Dysfunctions - Complete Phase 2B
Goal: Complete “Radical Candor” + “Five Dysfunctions” + Phase 2B Reflection
Day 134 (Monday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Radical Candor” - Part 1, Chapters 3-4 | 50 min |
| :memo: | Note: The Radical Candor framework | 10 min |
The Radical Candor Framework:
CHALLENGE DIRECTLY
^
|
OBNOXIOUS | RADICAL
AGGRESSION | CANDOR
| *
--------------------------> CARE PERSONALLY
|
MANIPULATIVE | RUINOUS
INSINCERITY | EMPATHY
|
Day 135 (Tuesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Radical Candor” - Part 2 (Getting, Giving, Encouraging) | 50 min |
| :zap: | Create 5 flashcards on Radical Candor | 10 min |
The 4 Quadrants:
| Quadrant | Description | Example |
|---|---|---|
| Radical Candor | Care + Challenge | ”I care about your growth, and you need to improve X” |
| Ruinous Empathy | Care but don’t challenge | Avoiding hard feedback to be “nice” |
| Obnoxious Aggression | Challenge without caring | Harsh criticism without humanity |
| Manipulative Insincerity | Neither care nor challenge | Political backstabbing |
Day 136 (Wednesday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “Radical Candor” - Part 2 continued | 45 min |
| :brain: | Practice: Prepare a candid conversation | 20 min |
AI prompt:
I need to give feedback to someone about [situation].
Help me prepare using the Radical Candor framework.
Ask me clarifying questions about:
1. What behavior I observed
2. What impact it had
3. What I want to see change
Then help me script the conversation so it's caring AND direct.
The Feedback Formula:
- Situation: What happened
- Behavior: What you observed
- Impact: Effect on you/team/work
- Question: “What’s your perspective?”
Day 137 (Thursday)
| Time | Activity | Duration |
|---|---|---|
| :headphones: | Complete “Radical Candor” | 50 min |
| :wrench: | Order/download “The Five Dysfunctions of a Team” | 5 min |
| :memo: | Self-map on Radical Candor grid | 10 min |
Self-Assessment: Where do you typically fall on the grid?
- Radical Candor (ideal)
- Ruinous Empathy (most common)
- Obnoxious Aggression
- Manipulative Insincerity
What pulls you toward Ruinous Empathy? _______________
Key Principles:
- It’s not mean, it’s clear - Withholding feedback isn’t kindness
- Criticism is a gift - When delivered with care
- Praise in public, criticize in private - Usually
- Get feedback before giving it - “What could I do better?”
Day 138 (Friday)
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Five Dysfunctions of a Team” - Part 1 (The Fable) | 50 min |
| :zap: | Create 5 flashcards on team dysfunctions | 10 min |
The 5 Dysfunctions Pyramid:
5. INATTENTION TO RESULTS
Focus on ego/status
^
4. AVOIDANCE OF ACCOUNTABILITY
Not holding each other accountable
^
3. LACK OF COMMITMENT
Ambiguity, no buy-in
^
2. FEAR OF CONFLICT
Artificial harmony
^
1. ABSENCE OF TRUST <-- FOUNDATION
Invulnerability, hiding weaknesses
Day 139 (Saturday) - Lighter Day
| Time | Activity | Duration |
|---|---|---|
| :books: | “The Five Dysfunctions” - Part 2 (The Model) | 50 min |
| :memo: | Diagnose a team you know | 15 min |
Team Dysfunction Diagnosis: Think of a team you’ve been part of. Which dysfunctions did you observe?
| Dysfunction | Present? (Y/N) | Evidence |
|---|---|---|
| 1. Absence of Trust | ||
| 2. Fear of Conflict | ||
| 3. Lack of Commitment | ||
| 4. Avoidance of Accountability | ||
| 5. Inattention to Results |
Fix Them Bottom-Up:
| Dysfunction | Solution |
|---|---|
| 1. Absence of Trust | Vulnerability exercises, personal histories |
| 2. Fear of Conflict | Permission to disagree, mine for conflict |
| 3. Lack of Commitment | Clear decisions, deadlines, alignment |
| 4. Avoidance of Accountability | Public goals, peer pressure, regular reviews |
| 5. Inattention to Results | Scoreboard, team-first rewards |
Day 140 (Sunday) - Phase 2B Completion + Transition
| Time | Activity | Duration |
|---|---|---|
| :books: | Complete “The Five Dysfunctions” | 30 min |
| :memo: | Complete Phase 2B Reflection Questions | 30 min |
| :wrench: | Update PROGRESS_TRACKER.md - Phase 2B complete! | 10 min |
| :wrench: | Order/download “Influence” by Cialdini | 5 min |
Trust = Vulnerability:
- Share personal stories
- Admit mistakes openly
- Ask for help
- Acknowledge weaknesses
Phase 2B Reflection Questions
Complete these before moving to Phase 2C:
-
How psychologically safe is your environment? (Rate 1-10)
- Score: ___
- What’s ONE thing that would increase it? _______________
-
Think of a recent failure. What type was it?
- Basic (preventable with process)
- Complex (multiple factors)
- Intelligent (hypothesis-testing)
- What did you learn? _______________
-
Map yourself on the Radical Candor grid:
- Where do you typically fall? _______________
- What pulls you toward Ruinous Empathy? _______________
- One conversation you need to have: _______________
-
Which of the 5 Dysfunctions do you see most often?
- In teams you’ve been part of: _______________
- How could you address it? _______________
-
Name 3 belonging cues you will practice:
-
Week 20 Checkpoint
After Week 20, you should have:
- Finished “Radical Candor”
- Finished “The Five Dysfunctions of a Team”
- Practiced preparing a candid conversation (with AI)
- Self-mapped on Radical Candor grid
- Diagnosed a team’s dysfunctions
- Completed Phase 2B reflection questions
- Watched 3 TED Talks (Edmondson, Heffernan, Sinek)
- Created 30+ flashcards (Phase 2B)
- Updated PROGRESS_TRACKER.md - Phase 2B complete!
Month 5 Complete!
What You’ve Accomplished
Phase 2B (Weeks 17-20):
- “The Fearless Organization” - Amy Edmondson (Psychological safety)
- “Right Kind of Wrong” - Amy Edmondson (Failing well)
- “The Culture Code” - Daniel Coyle (Building great cultures)
- “Radical Candor” - Kim Scott (Caring + Challenging)
- “The Five Dysfunctions of a Team” - Patrick Lencioni (Team health)
- 3 TED Talks (Edmondson, Heffernan, Sinek)
- 30+ flashcards
- Team safety assessment
- Failure audit exercise
- Candor practice
Time Invested
- Month 5 Total: ~30-35 hours
- Daily average: ~50 minutes
- Running total: ~140-155 hours
You Now Understand:
- How to create psychologically safe environments
- The difference between good and bad failures
- How great cultures are built (safety, vulnerability, purpose)
- How to give feedback that’s caring AND challenging
- How to diagnose and fix team dysfunctions
Next Steps: Phase 2C Preview
Phase 2C: Influence & Ethical Persuasion (Weeks 21-24)
You can create safe environments. Now learn how to INFLUENCE within those environments - ethically. Safety is the foundation; influence is the tool you use once safety exists.
Upcoming books:
| Book | Author | Why It Matters |
|---|---|---|
| Influence | Robert Cialdini | The 6 principles of ethical persuasion |
| Pre-Suasion | Robert Cialdini | Setting the stage before you persuade |
| Never Split the Difference | Chris Voss | FBI negotiation tactics |
| The Art of Gathering | Priya Parker | How to bring people together |
Key insight: Influence without safety is manipulation. Influence with safety is leadership.
Continue to Phase 2C: Influence & Ethical Persuasion
Troubleshooting
”I’m behind schedule”
This is completely normal! Options:
- Prioritize: If you can only read 2 books: “The Fearless Organization” + “Radical Candor”
- TED Talks: Edmondson’s and Sinek’s talks cover core concepts
- Audiobook: All five books have good audio versions
- Extend: Take 5-6 weeks instead of 4
”The Fearless Organization is too academic”
- Amy Edmondson’s TED Talk covers the core concepts (12 min)
- Focus on Chapters 1-3 and 8-9 for practical application
- Skip detailed research methodology chapters
”Radical Candor feels uncomfortable”
- Most people default to Ruinous Empathy - you’re not alone
- Start with lower-stakes feedback situations
- Practice with AI first to build confidence
- Remember: withholding feedback isn’t kindness
”Five Dysfunctions seems obvious”
- It’s a fable format - quick read, simple concepts
- Power is in the bottom-up sequence
- Diagnose a real team for deeper learning
- Use the free assessment at tablegroup.com
Quick Reference Card
Daily Routine (30-45 min)
- Flashcard review (5 min)
- Main reading (25-35 min)
- Reflection note (5 min)
Weekly Routine
- Monday-Friday: Main reading
- Saturday: TED Talk + lighter reading/audiobook
- Sunday: Review + reflection
Psychological Safety Questions (Edmondson)
- “What am I missing?”
- “What could go wrong?”
- “Who disagrees?”
- “What do you need from me?”
The 3 Failure Types
- Basic: Prevent with checklists
- Complex: Analyze without blame
- Intelligent: Celebrate the learning!
Radical Candor Formula
Care Personally + Challenge Directly = Radical Candor
The 5 Dysfunctions (bottom-up fix)
- Trust → Vulnerability exercises
- Conflict → Permission to disagree
- Commitment → Clear decisions
- Accountability → Public goals
- Results → Team-first scoreboard
Five months complete. You understand yourself (Phase 1), what motivates people (Phase 2A), and how to create safe environments for them to thrive (Phase 2B). Phase 2C teaches you how to influence and persuade within those safe environments.
Continue to Phase 2C: Influence & Ethical Persuasion
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