ToolTips

Small fixes.Real leverage.

Thirty practical playbooks for the people building, scaling, and operating modern software companies. Leadership, AI in SaaS, AI-native software, execution, operations, product, CX, and GTM. No gated PDF. No fluff. Steal anything that helps.

LeadershipAI in SaaSAI-NativeExecutionOperationsProductCXGTM
Full library

Thirty playbooks, organised by topic.

Leadership

The single-thread principle: one owner per outcome

When two people own a problem, no one does. The simplest, hardest discipline in operating a growing company.

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Leadership

The 70% decision rule: decide before you are certain

Most operating decisions get worse, not better, the longer you wait. A framework for deciding with what you have.

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Leadership

Async by default: meetings as a tax, not a strategy

Most meetings exist to compensate for missing writing. An operating system that treats meetings as the exception.

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Leadership

Skip-level conversations: what your directs cannot tell you

The most accurate picture of how your company actually works lives two levels down.

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Leadership

The founder calendar audit: where attention actually goes

Your calendar is the most honest strategy document in the company.

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AI in SaaS

Bolting AI onto SaaS is a six-month strategy

Adding AI as a feature works until the AI-native competitor with 1/10 the surface area shows up.

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AI in SaaS

Cost-per-resolved-task: the unit economics of AI features

The first AI feature is easy to ship and easy to lose money on. The metric that keeps it honest.

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AI in SaaS

The eval suite is the new product surface

Shipping AI features without evals is shipping software without tests.

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AI in SaaS

Determinism where it matters, AI where it does not

Not every problem is an AI problem. A practical decision rule.

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AI-Native

What "AI-native" actually means (and what it does not)

A working definition that separates rebuilt-from-scratch products from a chat icon in the corner.

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AI-Native

Designing the human-in-the-loop seam

The most important UX decision in AI-native products is where the human enters and exits the loop.

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AI-Native

Memory architecture that does not leak

Agentic products live or die on what they remember and what they forget.

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AI-Native

The autonomy spectrum: from suggestions to outcomes

Agentic products earn autonomy step by step. A model for shipping along the spectrum.

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Execution

Speed is a strategy, even when you are right

Being correct slowly is usually worse than being approximately right quickly.

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Execution

The weekly close-out, not the weekly check-in

Most team rituals manage anxiety, not outcomes. The one weekly ritual that pays off.

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Execution

The pre-mortem: the meeting that saves projects

Post-mortems explain why things went wrong. Pre-mortems prevent it.

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Execution

The unit-of-work principle: make work finishable

Long projects hide their own progress. Break work into units finishable in a week.

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Execution

Default to writing: the operating habit that scales

Spoken decisions die. Written decisions compound.

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Operations

The five-handoff rule: where work goes to die

Every handoff between people or systems is a place work can stall.

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Operations

Make status ambient, kill the status meeting

A pattern for making status a property of the work, not a meeting.

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Operations

The shadow process map: what the org chart hides

Every company has two processes: the one in the wiki and the one that actually happens.

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Operations

Find the bottleneck, not the symptom

The loudest problem is rarely the real one.

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Product

The one-job test: what every feature must pass

Every feature is a tax on the user's attention. The test that decides whether a feature earns its place.

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Product

The shipping budget: capacity, not capability, is the constraint

Teams plan around what they could build. They should plan around what they can ship.

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Product

The inverse roadmap: what you are explicitly not doing

Every roadmap is a list of yeses. The list of nos is usually more strategic.

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Product

Feature graveyards: what you killed and why

The features you removed teach more than the ones you kept.

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CX

Time-to-aha: the only activation metric that matters

Most onboarding optimisation moves the wrong number.

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CX

The cancel page that saves accounts

What a thoughtful cancel flow recovers, and what an honest one teaches.

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GTM

Outcome-based pricing: what to charge when AI does the work

Per-seat pricing was designed for software where the user did the work. AI changes who does the work.

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GTM

The activation moment: where free becomes paid

Most companies measure conversion. Few design for it.

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Tell us where it hurts

Tell us where the work gets hard.

Whether it is a tangled workflow, a product idea, or an operation that has quietly stopped scaling, we would like to hear it. No pitch deck required.