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The Pitt

3 recommend/use · 3 sourced episodes

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Self-Mastery3 steps

AI Introspection Rubric

Point an AI agent at a folder of your own notes to surface criteria you hold implicitly and turn them into a rubric.

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Influence4 steps

Anchor the Pitch to the Exec's Incentives

Find the metric, OKR, or board pressure they own, then show how your idea moves it.

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Strategy3 steps

Building Trust Through Speed

Ship an honest 'research preview' early, then visibly iterate on feedback so speed builds trust instead of eroding it.

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Leadership3 steps

Deliberate Low-Leverage Leadership

Choose the nitty-gritty tasks 'anyone could do' — because when a senior leader does them, they become high leverage.

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Leadership3 steps

Follow the Breadcrumbs and Calibrate Urgency

Act fast on an exec's subtle hints, but ask how strongly they actually feel first.

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Innovation3 steps

Legibility Framework for Spotting Frontier Ideas

Hunt for illegible ideas — the ones with real energy that nobody can quite articulate yet — and translate them.

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Finance4 steps

Net Revenue Retention Above 100% (and Why NRR Lies)

Expansion revenue must beat churn, but NRR flatters you — watch logo churn too.

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Sales4 steps

Pricing Selects the Market (Sell Growth, Not Savings)

Price and positioning choose your market — reframe your product as growth to charge many times more.

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Leadership3 steps

Roasting Plus High Standards

Let the team feel safe enough to roast you, then apply high standards without fear — safety makes rigor easier.

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Influence3 steps

Shrink the Change to Build Trust

De-risk a scary idea into a two-week experiment with a fixed check-in date.

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Communication3 steps

Stewart Plus Two More

Never bring one option; show a Goldilocks three and hold the rest in the appendix.

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Productivity3 steps

Stratified Design Work

Split your time between supporting engineers' execution and setting a 3-6 month vision, not polishing mocks.

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Strategy5 steps

The 5-Question Stalled Growth Diagnostic

Diagnose why growth is slowing by asking five questions in strict priority order.

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Communication4 steps

The 60-Second Meeting Reset

Buy a context-starved exec 30 seconds of orientation before you pitch.

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Finance3 steps

The Cancellation Ceiling (Maximum Customer Cap)

New customers divided by cancellation rate is the hard ceiling on how big you can ever get.

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Marketing3 steps

The Elephant Curve (Channels Saturate and Sag)

Every acquisition channel starts as an S-curve then sags — assume your winners will decline.

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Communication3 steps

Themes for Discussion at the Top of the Doc

Bubble up the spiciest 3 topics live; answer the hundred nitpicks offline.

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Marketing5 steps

The 'What Made You Cancel?' Rooter-Cause Diagnosis

Ask what made them cancel (not why), then dig past the surface reason to the real causes.

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Leadership4 steps

Three Designer Hiring Archetypes

Hire for one of three profiles — block-shaped generalist, deep-T specialist, or the crack new grad.

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Influence4 steps

Treat the Executive as Your Key User

Run stakeholder conversations as discovery interviews, not approval requests.

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