Leadership

Day 01Designing 1:1sAgenda · Trust · Real signal · Beyond status Day 02The Craft of FeedbackRadical Candor · SBI · Now vs Later · Channel Day 03The Craft of Perf ReviewAnatomy · Calibration · Bias · Why not Exceeds Day 04The Craft of Hard ConversationsThree layers · Firing · Promo denial · Blameless PM Day 05The Craft of HiringBar raising · Structured interview · Scorecard · Rejection Day 06Office Politics 101Power map · Player types · Stakeholder grid · Reciprocity Day 07The Art of DisagreementWorth the fight · 7 phrasings · Escalation ladder · Disagree & commit Day 08Cross-Functional InfluenceCurrencies · Stakeholder map · Pre-wiring · Make it their win Day 09Managing UpRead the calculus · Self-advocacy · One-page memo · Shit umbrella Day 10Sun Tzu in Org PoliticsCourt calculus · Strike the void · Know yourself · Win before the meeting Day 11Stoic Work SurvivalDichotomy of control · Premeditatio malorum · Obstacle as material · Daily 10-min loop Day 12Onboarding30/60/90 map · First-30-days early win · Network & tacit culture · Fresh eyes Day 13DelegationDelegation matrix · 7-level trust ladder · Give the monkey back · Guardrails not surveillance Day 14CoachingGROW model · Advice monster · 7 power questions · When not to coach Day 15Decision ArchitectureOne-way vs two-way door · RAPID · DACI · Disagree & commit Day 16Strategy & DirectionNorth Star metric · OKR design · Strategy memo · Embracing uncertainty Day 17Team MeetingsMeeting taxonomy · Standup vs all-hands · Facilitation · Cut & async Day 18Async Culture & Doc-FirstOne-page memo · RFC culture · ADR records · Cutting meeting load Day 19Conflict ResolutionTask vs relationship conflict · Mediator not judge · Hand it back · Clean escalation Day 20Leading Under PressureThe first hour · Delivering layoffs · Blameless postmortems · Aftershock & self-command Day 21Psychological SafetySafety ≠ niceness · Leader goes first · Engineer dissent · Artificial harmony Day 22Identity Beyond TitleRole ≠ identity · Single point of failure · Identity portfolio · Title-free intro drill Day 23Impermanence at WorkImpermanence as default · Dichotomy of control · Pre-written Plan B · Don't outsource security Day 24Envy & ComparisonEnvy targets peers · Benign vs malicious · Choose your frame · Mudita Day 25Failure & ShameShame vs guilt · Public-failure narrative · CV of failures · The three P's Day 26Active Listening & Premise AlignmentFour levels of listening · Surface the premise · Load-bearing first · Fact vs value claim Day 27Survival for the ApoliticalThe cost of opting out · Minimum viable politics · Limits of letting work speak · Win through allies Day 28Ethical Boundaries & Saying NoThree-layer triage · Refusal spectrum · Sunlight email · Exit/Voice/Loyalty Day 29Meaning at WorkThree-source diagnostic · Bullshit-job moments · Job crafting · Don't outsource it Day 30Luck & AttributionTalent+luck · Survivorship on yourself · Humility as calibration · Luck in the retro Day 31Playing the Long GameFinite vs infinite games · What compounds · Valley of disappointment · Long-term people Day 32The Undervalued YearsPsychology of being overlooked · Visibility vs hype · Discipline of quiet accumulation · When to walk Day 33Money & Career FreedomFU money as option · Buffer as BATNA · Lifestyle inflation · Freedom is an option not escape Day 34Diversity & InclusionIn-the-moment intervention · De-bias the system · Data-driven funnel · Sponsorship over symbolism Day 35The Cost of AuthenticityMask as social interface · Adaptive authenticity · The line you don't cross · When the mask fuses Day 36Team Building & CohesionRituals compound · Off-sites for in-person work · Celebrate progress not outcomes · Belonging ≠ sameness Day 37Leadership StyleSwitch six styles · Match the person (SLII) · Dose of vulnerability · Authenticity paradox Day 38Time Management for LeadersMaker vs manager schedule · Calendar defense · Scripts for saying no · Deep-work blocks Day 39Strategy vs ExecutionThe strategy kernel · From firefighting to prevention · A weekly zoom-out cadence · The hidden invoice of short-termism Day 40Building Company CultureCulture is what you reward · Schein's 3 levels · A testable contract · Founder's mentality · The culture handoff Day 41Startup vs Big-Company LeadershipWartime vs peacetime · Two muscles · The intrapreneur's trap · Unload & rebuild Day 42Women in LeadershipThe double bind · The Lean In debate · The invisible tax & credit · Sponsorship vs the motherhood penalty Day 43Career StrategyScarce×strong positioning · Promotion is lagging · Manager/IC pendulum · Pivot & stop-loss timing Day 44Mentors & SponsorsTalks to vs talks about you · A sponsor is earned · Arm them, don't shame them · ABCD to sponsor others Day 45Personal BrandBrand is what they say · Internal visibility before external fame · Compound your work · Consistency dividend & authenticity bill Day 46Endurance & the BodyBurnout's 3 clinical dimensions · Manage energy not time · Design rest as training · Jump to the second curve Day 47The Graceful ExitFailed voice is the go signal · Craft of the resignation talk · Don't burn bridges · Path to IC/independent consultant Day 48Cross-Cultural LeadershipHigh/low context reads the unsaid · Surface dissent in high power distance · Consensual vs top-down decisions · CQ dodges stereotypes Day 49Storytelling LeadershipWhat is/what could be for vision · ABT for change · Signature stories bank values · One face + a set of numbers Day 50Data-Driven ManagementGoodhart's trap & paired indicators · Qual fills quant blind spots · Falsifiable experiments · Intuition vs. data jurisdiction Day 51Ethical LeadershipPre-script moral courage · Badaracco's five questions for gray decisions · Hirschman's dissent ladder · The real cost of values Day 52Scaling LeadershipLeverage: from people to systems · Conway's Law & org design · Communication dilution & anti-decay · Culture institutionalized via incentives Day 53Generational ManagementGenerational gaps overstated · manage the person · Why before What · feedback in small daily doses · supporter not therapist Day 54Managing in the Age of AICentaur human-AI division of labor · scarcity moves from doing to judging · honesty over reassurance on anxiety · human in the loop, sign-off doesn't outsource Day 55The Leadership Dimension of Negotiationstep back from positions to interests · BATNA is the footing to walk · sequence moves in multiparty talks · read what goes unsaid across cultures Day 56The Psychology of Powerpower corrodes the skills that got you up · status switches off perspective · Level 5 credit out the window, blame in the mirror · truth decays up the hierarchy, rebuild the loop Day 57Succession & Legacyplan on potential not current output · let successors own real mistakes · the founder's graceful handoff · clock-building beats time-telling Day 58Leading Creative & R&D Teamsmanaging creatives · autonomy & direction · safety & innovation · tolerating failure Day 59Remote & Hybrid, Deeperasync-first · trust vs surveillance · hybrid fairness · digital presence Day 60Boards & Governancehow boards work · stakeholders · corporate governance · CEO–board relations Day 61Leading Through Adversityleading through the trough · humane layoffs · restructuring · hope vs reality Day 62Humble & Vulnerable LeadershipLevel 5 leadership (Collins) · the power of vulnerability · admitting you don't know · limits of authenticity Day 63Lessons from War & Sportmission command · the coaching philosophy · team cohesion · decisions under pressure Day 64The Conductor Metaphorthe conductor makes no sound · listening & sync · jazz vs classical · collective creation Day 65Organizational Learning & Knowledgeretro culture · knowledge management · learning from failure · institutional memory Day 66Public & Nonprofit Leadershipthree metric layers & the counterfactual · mission can't buy overtime · the contributor funnel · legislative leadership Day 67Attention & Energythree attention slots · attention residue & interrupt governance · one-way doors at peak · attention is a public signal Day 68Culture as Operating Systemmatch the lever to the layer · rituals are the runtime · promotion is the loudest write · book your culture debt Day 69The Leader's Inner Workcalibrate, don't introspect · the shadow disguised as judgment · mindfulness as protocol · burnout reads the environment Day 70Sponsorship That Doesn't Fadesponsorship is a schedulable workload · decay hits in weeks 6–12 · the "frozen middle" is misaligned incentives · absorption has a hard ceiling Day 71Two Sets of Books on the AI Budgetkeep the funnel ledger and the P&L ledger apart · funding the next round on savings never delivered · the six dials behind any ROI · set the bar before you fund it Day 72When the Evidence Doesn't Support the Decision You Already Madeworth doing ≠ proven to work · you implement a dose, not a label · staying falsifiable after you've announced · when someone cites a study at you