On Writing Well

Answer the Question Behind the Question

When caught without a number, answer the adjacent question and surface the real concern.

Leadership5 steps

CEDAF Delegation Framework

A five-part checklist for delegating without lowering your standards — to humans or AI.

Innovation4 steps

Complaint Storms

A team ritual to see your own product with fresh, critical eyes — by first ripping apart someone else's.

Manage Up by Sharing Your Point of View

Bring your manager a recommendation to react to, not an open question to solve.

MOO — Most Obvious Objection

Spend two minutes pre-empting the objection you'll obviously get, and stop feeling blindsided.

Finance4 steps

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

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

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.

Innovation3 steps

Principles for Building Trustworthy AI Products

Match UI confidence to data quality, be transparent about sources, and design virtuous data cycles.

Strategy5 steps

Re-establishing Product-Market Fit (Stacking S-Curves)

When growth plateaus, throw away the roadmap, sacrifice impact for learning, and rebuild PMF for the next audience.

Communication5 steps

Ruthless Simplification for PM Writing

A set of concrete tools to strip PM documents down to only what's necessary.

Influence4 steps

Sales Then Logistics

Sell the why before you explain the how, or your ask gets crickets.

Signposting

Use structural cue-words to guide the reader through your writing without heavy formatting.

Influence4 steps

Speak Accurately (Avoid the Single-Minded Martyr)

Match your stated confidence to your actual evidence — neither overreach nor over-hedge.

Start-With-Why One-Pager

The PM's core artifact: define the thing by nailing the problem and why-now before anything else.

Strategy Not Self-Expression

Feedback's goal is behavior change, so cut everything that doesn't serve it — usually 90%.

Leadership6 steps

The 10 Traits of Great Product Managers

A definition of what the PM job actually is — facilitation, execution, and impact — not a career ladder.

Strategy5 steps

The 5-Question Stalled Growth Diagnostic

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

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.

Mindset3 steps

The Data-Driven Red Flag

When someone brags about being 'data-driven,' suspect weak product judgment, not strong analytics.

Strategy4 steps

The Diversified Roadmap Portfolio

Treat a product roadmap like an investment portfolio, balanced across three axes of risk and intent.

Marketing3 steps

The Elephant Curve (Channels Saturate and Sag)

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

Strategy8 steps

The Landscape-First Product Strategy Doc

A bullet-driven Google Doc that builds an unbroken logic chain from company mission down to a single team priority.

Innovation4 steps

The Pilot Program for De-Risking Launches

Build a diverse champion network of real customers to test new features in the wild before you ever launch.

Self-Mastery3 steps

The Swipe File

Capture examples of communication that work — the act of collecting trains your eye.

The Three Threads of Great PMs

The three durable behaviors that separate great product managers from good ones, in any company type.

The U-Curve of Founder Involvement

Involve a product-minded founder heavily at the start and end of a project, but give the team space to run in the middle.

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.