A ten-minute executive walkthrough

How I use AI to make better product decisions.

At three moments—before I commit, before I align a room, and while the team delivers—AI helps me challenge assumptions, make strategy tangible, and find patterns humans miss. I still own every decision.

One fictional business. One decision thread. Three different jobs for AI.

One decision threadIdeate → Align → Deliver

Before I commitIdeate

Broad bet → conditional decisionA weak attach rate forces the strategy to confront what must be true.

Before I alignAlign

Strategy memo → clickable experienceCustomer value, platform work, and controls evolve together.

While we deliverDeliver

Ticket noise → evidence-backed signalThe team pulse and work record expose a normalized source of delay.

Guardrail: these are invented, personal working examples. Production use belongs inside approved tools, approved sources, and established controls.

01 · Ideate Tested personal prototype

Napkin → Narrative

Turn a conviction into a decision that can be proven wrong.

The leadership questionAm I making the right bet?

Human provides

A conviction, context, and the decision at stake

AI uniquely does

Interrogates weak assumptions and retrieves opposing evidence

Human decides

What changes—and what test settles the argument

FieldFlow distribution strategyInvented working example

The flawed conviction

“Distribution is the whole game. Integrate broadly now; optimize attach later.”

11% attach vs. 30% planning assumption

The two questions that changed the work

1What evidence distinguishes a discovery problem from a workflow problem?

2What has to be true for breadth itself to solve the customer’s problem?

Retrieved defender Dharmesh Shah’s documented lens

Broad can work when integration burden—not feature depth—is the customer’s core problem. AI synthesis, not a direct quote.

Source · Apr 2024 ↗

Retrieved critic Jake Fuentes + Annie Pearl lenses

Breadth across disconnected buyers frays the ICP; focus is a choice about where to play. AI synthesis, not a direct quote.

Sources · 2023 ↗

Before · slogan

Go broad now. Fix attach later.

01A · The custom analysis engine

A prompt can draft. A tool can remember how to think.

I built the archive into a reusable reasoning system: structured evidence in layers, retrieved only when the decision needs it.

624posts + episodes

15,669typed evidence fragments

4,367opposing-view pairs

345guest profiles

Build once · turn unstructured expertise into an evidence system

01

Source archiveA dated, licensed personal snapshot of posts and transcripts

02

AI extractionFrameworks, claims, contexts, caveats, and contrarian positions

03

Tension graphA second pass connects positions that genuinely disagree

04

Layered memoryFast summaries, curated evidence, and source-level escape hatches

Use on every decision · bring in only the evidence this claim needs

Read the claimFind what must be true

Retrieve by meaningNot just keyword match

Prefer tensionDefender + critic + condition

Return a traceSource, date, status, human check

Challenge · horizontal product criteriaJake Fuentes argues that horizontal products work when one audience has many connected needs—not when many audiences each have one use case.
Newsletter · Oct 31, 2023 ↗

Condition · when broad can be rightDharmesh Shah’s HubSpot example supports breadth when integrating fragmented tools is itself the customer problem.
Podcast · Apr 4, 2024 ↗

Derived analysis from a frozen Lenny’s Newsletter / Podcast subscriber-archive snapshot. No raw archive files are redistributed. Source credit: Lenny Rachitsky. Not affiliated with or endorsed by Lenny’s Newsletter.

The model proposes; the evidence constrains; I decide.Named viewpoints appear only when retrieval finds dated support. Otherwise the tool uses unlabeled expert lenses and marks the result “needs human review.”

02 · Align Tested personal prototype

The Playable Roadmap

Make the strategy tangible enough to react to.

The leadership questionCan everyone see the same future?

Human provides

The chosen strategy, north star, and constraints

AI uniquely does

Translates each stage across experience, platform, value, and controls

Human decides

What is coherent, feasible, and worth funding

Field-services-first roadmapOpen full clickable mock ↗

Customer experience

Value unlocked

Capability stack · new in indigo

Proof measure

Northside HVAC

03 · Deliver Tested on synthetic data

Team Pulse

Reconcile how work feels with how work moved.

The leadership questionCan the organization deliver the bet?

Human provides

An anonymous pulse, scoped work record, and decision context

AI uniquely does

Groups prose into themes, links evidence, and compares the two signals

Human decides

Which hypothesis to investigate and what system to change

Team Atlas · 90-day signal review412 synthetic tickets · 9/11 pulse responses

Signal one · anonymous pulse

What the team raised

Ranked aggregate themes from scores plus free text.

01Partner sandbox stability8 mentions

02Review queue load6 mentions

03Webhook retries5 mentions

04Integration ownership3 mentions

Signal two · scoped work record

What the work record grouped

AI-proposed themes; each reviewed against its linked tickets.

01 · Partner sandbox38 tickets · 4.8d median added wait

02 · Integration ownership22 tickets · 6.2d median added wait

03 · Webhook retries17 tickets · 3.1d median added wait

04 · Review queue14 tickets · 2.7d median added wait

The signal gap
A normalized boundary is slowing the roadmap.

ATL-184“Waiting for platform to confirm which team owns the merchant-state mapping.”

ATL-207“Moved back to Atlas after two days; integration team says the adapter is ours.”

ATL-231“Blocked again on the same ownership question from the milestone-payment flow.”

Directional method: added wait = first blocked transition to first subsequent active transition. Median shown; overlapping themes are not summed.

AI proposes themes. A human reviews every theme before leadership sees it. Read-only sourceScoped fieldsNames redactedNo individual scoring

The operating habit

Three moments.
One standard.

Ideate

Challenge the assumption before commitment.Turn conviction into a falsifiable decision.

Align

Make the strategy tangible before consensus.Let the room react to one shared future.

Deliver

Reconcile signals before intervention.Act on evidence, not the loudest anecdote.

AI handles interrogation and synthesis. I own the evidence, the decision, and the consequences.

01

A responsible next step

Run one bounded pilot.

Use an approved environment, sanitized or synthetic inputs, and a decision important enough to learn from—but safe enough to stop.

✓One named decision owner and one human reviewer

✓Read-only, minimum-necessary source access

✓Success, stop, and escalation criteria agreed in advance

✓Every important claim traceable to evidence

Explore the methods

How I use AI to make better product decisions.

Napkin → Narrative

A prompt can draft. A tool can remember how to think.

The Playable Roadmap

Team Pulse

What the team raised

What the work record grouped

Three moments.One standard.

Run one bounded pilot.

Three moments.
One standard.