Summary

Key Quotes

It's not mean, it's clear What could I do or stop doing that would make it easier to work with me?

Management reduces to two axes: care personally and challenge directly. When both are high, you get radical candor—clear, compassionate communication that builds trust and drives results. Most managers default to ruinous empathy (caring without challenging) because direct feedback feels cruel, but withholding honest guidance is actually the crueler path. The operating system is a cycle: listen → clarify → debate → decide → persuade → execute → learn. Boss-level execution means weekly 1-on-1s where the direct report sets the agenda, career conversations that surface each person's life goals (not just company goals), and a culture where criticism of management is not just tolerated but actively solicited.

Key Takeaways

Two axes: care personally × challenge directly

• Radical candor = high care + high challenge; ruinous empathy = high care + low challenge
• Obnoxious aggression and manipulative insincerity fill the other quadrants
• Criticize the work in context, never the character—fundamental attribution error is the enemy

Solicit criticism before giving it

• Ask 'What could I do or stop doing to make it easier to work with me?' and mean it
• If you disagree: agree with one aspect, paraphrase back, then schedule follow-up
• Toyota's big red square: three criticisms of management required—make feedback structurally unavoidable

Rockstars vs. superstars need different management

• Rockstars want stability and mastery; superstars want steep growth trajectories
• Don't force everyone into the growth track—recognize and reward excellent steady-state performers
• Believe everyone can be exceptional, but exceptional looks different for different people

The GSD wheel drives collaborative results

• Listen → Clarify → Debate → Decide → Persuade → Execute → Learn, then repeat
• Quiet listening (hide your thoughts) and loud listening ('here's a dopey idea') serve different moments
• Obligation to dissent: assign devil's advocates; pause for emotion; set clear decision timelines

1-on-1s and career conversations are the real work

• 50 minutes weekly, casual, direct report sets the agenda
• Career conversations: start with life story, probe motivators, map to 18-month plan
• Skip-level meetings support the manager—anonymous, shared notes, prioritize issues, review progress

Performance reviews should separate development from compensation

• No surprises: reviews must align with ongoing feedback
• Separate development review and pay discussion by a quarter
• Ratings: transparent, calibrated, 3-4 categories, sourced from up, down, and sideways

• Todo

Notes

Preface

• Not the same as radical transparency
  • Doesn’t account for privacy
• Compassion = empathy + action
• Building good relationships is core to the job

1: A new management philosophy

1: Build radically candid relationships

• Boss = leader + manager
• Bosses guide a team to achieve results
  • ^ guidance, team building, results
• Radical candor: develop trust: two axes:
  • Care personally: more than just work
  • Challenge directly: demand results
• Candor: communicate clearly, with humility
  • Offer your view of what’s going on
• Encourage the challenging of others

2: Get, give, and encourage guidance

• Operationalizing good guidance
• “It’s not mean, it’s clear”
• Radically candid praise:
  • Contextualized, personal, specific
• Radically candid criticism:
  • Be humble, do it in private
  • Don’t attach to character
• Don’t admit wrongdoing (politics), rather understand other perspective, find solution
• ask for criticism and show you can take it
• start giving radical praise, then criticism
• Toyota combatting taboo against criticizing management: big red square, 3 criticisms*
• Fundamental attribution error: criticize the work within context, not character
• Confidence in abilities, 2) work is shit, 3) why, 4) offer to help improve
• Eg. “your fly is down” or “spinach in teeth”

3: Understand what motivates each colleague

• Know how the job fits in to each person’s life goals
  • Don’t force a particular meaning
• Rockstar vs superstar
  • Seek very different roles
• Performance + growth matrix
  • Don’t force everyone to grow
• Spend more time with people doing the best work
• Peter principle vs promotion obsession
  • Recognize, reward rockstars
• Empower superstars:
  • Constantly challenge
  • Promote quickly
• Believe that everyone can be exceptional
• Reasons for poor performance:
  • Placed in wrong role
  • Too much too fast
  • Team culture fit
  • Personal change

4: Drive results collaboratively

• Insist people tell you when you’re wrong
• Get stuff done wheel: (GSD)
  • Listen: create a culture of listening
  • Clarify: space for sharpening
  • Debate: test rigorously
  • Decide
  • Persuade
  • Execute
  • Learn
• Quiet listening: hide your thoughts, honesty
• Loud listening: challenge others to object
  • “here’s a dopey idea”
• Responsibility for communicating idea falls on the speaker, not the listener
  • Push people to clarify ideas
• Rock tumbler debate → polished people:
  • Ideas, not egos
  • Make them switch roles
  • Obligation to dissent: devil’s advocate
  • Pause for emotion break
  • Set the scene / mood
  • Clarify decision timeline (not endless)
• Have a clear decision making process: ↓
• How to make the best possible decisions:
  • Facts, not recommendations
  • Go spelunking: direct to source
  • Persuasion is important
• Elements of rhetoric:
  • Ethos, logos, pathos
  • Humorous responses to awkward Qs
  • Credibility: with humility
  • Logic: show your work
• Consistency vs changing one’s mind:
  • When changing direction, clearly explain why

2: Tools and techniques

5: Relationships

• Establish trust with direct reports
• Stay centered
• Provide a sense of autonomy, agency
• Build trust: care personally
• Be weary of sharing values
• Be able to navigate personal space
  • Hugs: > 6 sec
• Master reactions to others emotions
  • Acknowledge: “I can see you’re”

6: Guidance

• Ideas for getting/giving/encouraging praise and criticism
• Bosses should encourage criticism of self from others in public to build trust
  • Go-to question: “what could I do or stop doing that would make it easier to work with me?”
  • If you disagree: 1) agree with some aspect, 2) clarify by parroting back, 3) schedule time to talk about it again
  • Orange box: anonymous feedback
• Humble feedback:
  • Situation + behavior + impact
  • State your intention to help: “I’m going to describe a problem I see. I may be wrong, and if so, I hope you’ll tell me. If I’m not, I hope my bringing it up will help you fix it.”
  • Give feedback promptly
  • Deliver guidance in person
  • Don’t personalize
  • Get feedback on your feedback: put stickers on a radical candor compass
• Listen, challenge, commit
• “I’m worried you’re pulling your punches”
• Formal performance reviews:
  • No surprises: review should be in line with regular feedback,
  • Ask for brief peer reviews:
    • +, ++, +++: inquire into anomalies
  • Ask for self (manager) review first
    • Insight into their mental state
  • Don’t do back-to-backs
  • Half looking back, half looking forward
  • Agree on a plan + schedule check-ins
  • Separate perf, comp reviews by a quarter to focus on each in turn
  • Killer whale, whoopsy-daisy feedback
    • Grant immunity
• Skip level 1-1s:
  • In support of manager, anonymous
  • Create shared notes (you write)
  • Praise → improve → what sucks?
  • Prioritize issues
  • Share right after meeting (refocuses)
  • Directs should then communicate learnings and changes to make
  • Review progress sometime after
  • Managing feedback:
    • Don’t defend, judge manager
    • Role: just passing along feedback

7: Team

• Avoiding boredom and burnout
• Have career convos to understand growth trajectory, aspirations and goals:
  • Articulate long-term vision, 18m plan
• Initial “get to know you” conversation:
  • Ask about “life story” and “dreams”
    • Probe into anecdotes
  • Identify, write down key motivators
    • Leadership, personal growth
  • “Dreams”, not career goals
    • Inquire deeper
  • → skills needed → 18 month plan
• Growth management plan:
  • ↑, -, ↓ and sanity check with peer
  • Don’t be an easy or hard grader
• Hiring process:
  • JD: describe culture and team fit
  • Pre-screen with skills assessment
  • Interview committee: 4 people
    • At least 1 from other team
  • Write down interview feedback
  • Don’t hire unless you’re dying to
• How to fire:
  • Don’t wait too long: push yourself to identify underperformance early
    • Fairest to employee, company, team, yourself
  • Talk to peers to share burden
  • Try a PIP
  • Give a damn about the person (care)
• Promotions:
  • Promotion committees
  • Don’t publicize promotions
    • Wrong objective
• Recognize high performers
  • Give regular thanks
  • Encourage gurus to teach
  • Public presentations
• Avoid absentee and micro-management

8: Results

• Things you can do to get stuff done together - faster
• 1-1s:
  • Make casual and fun
  • 50 mins per week (5h total per week)
  • Direct report sets the agenda
  • Good followup Qs:
    • How can I help?
    • What wakes you up at night?
    • What do you not want to work on? B/c you don’t like or b/c you think it’s not important?
    • What can you do to ^?
  • Encourage new ideas:
    • What do you need to develop that idea further so that it’s ready to discuss with the broader team?
    • I think I understand it but I’m not sure others will. Can you clarify?
• Staff meetings:
  • Clarify priorities for upcoming week
  • Learn: what went well? Badly?
  • Listen: 5-min status updates in shared doc
  • Clarify: identity key decisions, debates
    • Delegate to followup meetings
• Block out “think time”
• Debate meetings:
  • Slow down key decisions when needed
• All hands:
  • Presentations to persuade people that the company is making good decisions and headed in the right direction
  • Q+A so leaders can hear dissent and address it head-on
• Kannan boards
  • Encourage teamwork, respect
• Walk around (1h/week)
  • Find “the universe in a grain of sand”
  • Encourages detail orientation
• You’re under the microscope

Getting Started

1. Introduce radical candor to team: share your stories, show vulnerability
2. Prove you can take it before dishing it out
3. Begin career conversations + perfect your meaningful 1-1 conversations
4. Improve at impromptu guidance
   1. Be self-aware, culturally aware
5. Roll out big decision + debate meetings
6. Encourage guidance amongst team
7. Growth management plans for team
8. Encourage gauging each others guidance
9. Walk around
10. Skip level meetings
11. Hiring, firing, performance reviews

Afterword

• Self-awareness vs relational awareness: the impact you’re having on others
• Your stories: demonstrates self awareness, humility, genuine care
  • Radical candor
  • Obnoxious aggression
  • Manipulative insincerity
  • Ruinous empathy
• Improv: way to practice communication
• Psychological safety: a shared belief that a team is safe for interpersonal risk taking
• Google’s 5 key team dynamics:
  • Psychological safety
  • Dependability
  • Structure and clarity
  • Meaning
  • Impact
• Solicit feedback for every 1-1
• Signature questions:
  • “When should I be more or less hands-off with your work?”
  • “What could I do or stop doing to make it easier to work with me?”
  • “What’s something I could’ve done this week to make your job easier?”
  • “How can I best support your professional development right now?”
  • “What’s a blind spot of mine that you have noticed?”
  • “I feel like there’s something I’ve done wrong that I didn’t notice. Can you help me figure it out?”
  • “I know I’m not perfect. There’s probably 1000 things I do wrong every week. Why won’t anyone tell me?”
• Failing → “not yet”
• Talk publicly about feedback you’ve received and how you’re addressing it
• When challenging directly goes bad:
  • Name the emotion: “it looks like I’ve made you angry / sad”
• “It hurts for me to tell you this in the moment, but it’ll lead to…”

Performance reviews

• Separate development review and performance management (raises)
• Fairness is the goal
• rating or no rating
  • Transparency → fairness
• categories of ratings
  • Aim for 3-4: results, teamwork, innovation, efficiency
• job ladders
  • Unify across job types → fairness
• number of ratings
  • 1: not okay, 2: okay for now, 3: good, 4: great
• language matters
  • Humanize
• consequence of ratings
  • Be clear
• distribution of ratings
  • 5% 1s, 40% 2s, 40% 3s, 15% 4s
• forced curve or no
  • Don’t force but do pressure
  • Managers outside bounds → explain
• calibration of ratings
  • Transparency fairness
  • Recalibrate by level
• frequency
  • 2-4x per year
• 360 degree or manager’s unilateral
  • Source up, down, and sideways
• transparent or confidential
  • Transparent → fairness
• lightweight or heavyweight