Skip to main content
Month 5Weeks 16-1934h totalM7 Validated

Month 5: Psychological Safety

psychological safetyteam culturefeedback cultureradical candor
Duration
4 weeks
Study Time
34h
~9h/week
Daily Target
30-60
minutes

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

Flexibility Rules:

Icons:


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:


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:

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:

  1. Frame the Work - Set expectations for uncertainty and interdependence
  2. Invite Participation - Ask questions, genuinely seek input
  3. Respond Productively - Thank people for speaking up, even with bad news

Questions Leaders Should Ask:


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:

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:

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:


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:

  1. Set learning goals - Not just performance goals
  2. Create a failure-safe zone - Explicit permission to experiment
  3. Analyze failures - Blameless post-mortems
  4. Share failures - Make learning public

Questions to Ask After Failure:


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:

  1. How do you typically respond when you fail? _______________
  2. Do you distinguish between failure types? _______________
  3. What would change if you celebrated intelligent failures? _______________

Week 18 Checkpoint

Before moving to Week 19, you should have:

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


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:

Physical Cues That Signal Safety:


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

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


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:

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:

  1. Build Safety - Belonging cues
  2. Share Vulnerability - Leaders go first
  3. Establish Purpose - Simple, clear, repeated

Week 19 Checkpoint

Before moving to Week 20, you should have:


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:

  1. Situation: What happened
  2. Behavior: What you observed
  3. Impact: Effect on you/team/work
  4. 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?

What pulls you toward Ruinous Empathy? _______________

Key Principles:


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:


Phase 2B Reflection Questions

Complete these before moving to Phase 2C:

  1. How psychologically safe is your environment? (Rate 1-10)

    • Score: ___
    • What’s ONE thing that would increase it? _______________
  2. Think of a recent failure. What type was it?

    • Basic (preventable with process)
    • Complex (multiple factors)
    • Intelligent (hypothesis-testing)
    • What did you learn? _______________
  3. Map yourself on the Radical Candor grid:

    • Where do you typically fall? _______________
    • What pulls you toward Ruinous Empathy? _______________
    • One conversation you need to have: _______________
  4. Which of the 5 Dysfunctions do you see most often?

    • In teams you’ve been part of: _______________
    • How could you address it? _______________
  5. Name 3 belonging cues you will practice:





Week 20 Checkpoint

After Week 20, you should have:


Month 5 Complete!

What You’ve Accomplished

Phase 2B (Weeks 17-20):

Time Invested

You Now Understand:


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:

  1. Prioritize: If you can only read 2 books: “The Fearless Organization” + “Radical Candor”
  2. TED Talks: Edmondson’s and Sinek’s talks cover core concepts
  3. Audiobook: All five books have good audio versions
  4. Extend: Take 5-6 weeks instead of 4

“The Fearless Organization is too academic”

“Radical Candor feels uncomfortable”

“Five Dysfunctions seems obvious”


Quick Reference Card

Daily Routine (30-45 min)

  1. Flashcard review (5 min)
  2. Main reading (25-35 min)
  3. Reflection note (5 min)

Weekly Routine

Psychological Safety Questions (Edmondson)

The 3 Failure Types

Radical Candor Formula

Care Personally + Challenge Directly = Radical Candor

The 5 Dysfunctions (bottom-up fix)

  1. Trust → Vulnerability exercises
  2. Conflict → Permission to disagree
  3. Commitment → Clear decisions
  4. Accountability → Public goals
  5. 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


Previous: Month 4 Schedule | Next: Month 6 Schedule