/who-to-sell-toNEW

Who to sell to

Turn a founder's actual deals into an ICP they can sell against. The interview is the product: one topic at a time, evidence before opinions, a pattern named after every answer. The report is the record of what the interview found.

An ICP built from guesses describes who the founder wishes would buy. One built from paid, renewed and lost deals describes who actually buys and when. Keep pulling the conversation back to the second kind.

Choose the mode

State the mode you picked in one line, so the founder can correct it.

• Interview (default): no ICP exists, or the founder wants a fresh start.
• Fast path: the founder pastes a deals list, CRM export, invoice list or notes. Build the evidence table from it, then ask only about the gaps (usually why deals were lost and who approved the money).
• Review: the founder shares an existing ICP or positioning doc. Read it, then ask only the questions that test its weakest claims.
• Refresh: an earlier icp-report.html or ICP doc exists. Ask which deals happened since, update the evidence table, and say which ICP lines changed and why.

Before the first question

1. Read what is already there: the conversation, attached files, the working directory (an earlier report, a pricing page, a deals file), memory and connected tools. Never ask for something you can find.
2. Check for web access. If you have web search or page fetching, research the company and every customer or prospect the founder names before asking about them: what they do, who their users are, stage and funding. Scrape only public pages. Never fetch a private page or log in on the founder's behalf.
   • Without web access, say so in one line and ask for the three facts you need instead: what the company sells, to whom, and the names of its last paying customers.
   • Label anything researched as "found online" and anything told as "you said". Research can be stale or wrong; the founder corrects it.
3. Read references/frameworks.md once, so follow-ups draw on the right ideas.
4. Open with a short briefing, then ask question 1. In one message: what you found about the company (two to four lines, so the founder can fix it), how this works (about 10 to 15 questions, one at a time, a designed report at the end, 20 to 30 minutes), and the shortcut ("paste a deals list or CRM export any time and I'll skip ahead"). If something found online contradicts what the founder says, ask before assuming either is right.

Run the interview

Use references/question-bank.md. Adapt it to what you already know and skip what is answered, but keep the stage order: paying customers, then triggers, lost deals and buyers, then acquisition, then the second ICP if there is one, then content, then goals and capacity.

After every answer:

1. Name the pattern in two to four sentences, tied to the specific deal. For example: "They loved the pilot and still didn't renew, and the person who signed it left the company a month later. That's your sharpest filter: the buyer has to be someone who stays."
2. Show the running ICP once there is enough to state it, as a compact card of the five fields. Update it as answers change it.
3. Ask one question. Several sub-parts about the same deal are fine. Two different topics are not.

Make it easy to answer

• Offer two to four short options where the answer is a choice (excited, polite, still deciding), with room for "something else".
• Say which question this is and how far along you are ("Question 4 of about 12").
• Accept rough numbers, voice-note style rambling and "I don't know". Turn "I don't know" into a named open question and move on.
• When the founder says "skip", skip. When they say "that's enough", go to the report.

Rules that make the interview work

• One topic per turn. A list of questions gets a list of shallow answers.
• Evidence over opinion. Ask what happened, not what they think would happen. Money paid, renewals, introductions and urgency count. "They loved it" counts only when something followed it.
• Push back on vague answers, kindly and specifically. "AI companies" or "SMBs" is a category, not an ICP. Name what is missing and ask for it.
• Say so when the founder is wrong, with their own evidence. If they say contact level doesn't matter, show the deal that stalled with a junior contact.
• Separate proven from assumed. Mark claims with no evidence yet as hypotheses in the report, with what would prove them.
• When the founder gives context instead of an answer, acknowledge it, say what it adds, and ask the question again.
• Watch the quiet details: who approved the money, how the first meeting happened, what happened right before they bought. Those usually decide the ICP.
• Do not invent. Never fill a field with a plausible guess. Write the open question.

When to stop

Stop once every field of the ICP card has evidence or a named open question, and you know the 90-day goal and weekly hours. That is usually 10 to 15 questions. If the founder stops early, write the report with what you have and list the gaps.

Deliver the report

Read references/report-guide.md before writing. It defines each section and what makes it good.

Choose the format by environment:

• Filesystem available (Claude Code, Codex, Cursor): copy assets/icp-report.html to icp-report.html in the working directory, or a path the founder names. Replace every example value with this founder's content. Open it in the browser if you can.
• Chat only (Claude app, no files): create a doc or publish a page with the same sections. If the founder wants a file, produce the HTML.

Working with the HTML template:

• It is a finished example report for a fictional company called Fieldwork. Keep the structure, classes and styles. Replace all content. Add or remove table rows and list items as needed.
• The page opens on the ICP card and a short "This week" box. Every other section is a collapsed <details> row whose summary line is that section's one-sentence conclusion. Deals, sales-plan blocks and content channels nest one level deeper. Write every summary line as a finding, never a label.
• Delete any section with no content rather than leaving placeholders. The ICP card at the top is required.
• Keep the inline expand-all script at the bottom. The page must still read correctly with it removed.
• When finished, search the file for Fieldwork, Example and data-example. Any hit means example content is left. Replace it.
• Keep it self-contained: inline CSS only, no external fonts, scripts or images, so it renders the same everywhere and prints cleanly to PDF.

Check before handing over

1. Traceability. Every ICP card line points to a deal in the evidence table, or carries "(to test)".
2. Confidentiality. Point out anything sensitive: customer names with prices, lost deals named, salaries, someone else's personal details. Offer an anonymized copy if the founder will share it publicly.
3. Rendered output. If you can open the file, check that it loads, the card reads at phone width, and no example text remains.

After the report

End with one short paragraph naming the single most important thing to do this week. Then offer to refine a section or run the next step, such as a target list built from the ICP's triggers or outreach drafted with the cold-outreach skill.

Frameworks behind the interview

Seven sources, condensed to what the interview actually uses. Read once before question 1. Paraphrase these ideas in conversation; don't lecture the founder about them.

1. PostHog: ICP vs persona, and validating with data

Source: PostHog newsletter, "The ideal customer profile framework".

• An ICP describes the companies (or people) who need the product and will pay: type, size, who their customers are, who uses it, what they replace, what they value. A persona describes one user's motivations. Building only for a persona gets you love without revenue.
• A narrow ICP shapes everything downstream: pricing, sales motion, content tone, roadmap.
• Validate with behaviour, not interviews alone: in-ICP customers should retain better, use more, and refer more.
• Real enthusiasm: inviting colleagues unprompted, heavy use of a rough product, referrals, wanting to pay. Polite interest: "interesting", "cool", won't pay, hands you to someone junior.
• Don't lock in on one or two outlier customers. Five similar paying customers is a good sign, ten is strong.

Use it for: pushing back on "they loved it" and asking what happened next.

2. Lenny Rachitsky: three narrow attributes and the signs you've found it

Source: Lenny's Newsletter, "How to identify your ideal customer profile (ICP)".

• Most founders got the ICP wrong at first. Successful ones picked at least three attributes and went uncomfortably narrow.
• Attribute categories: company size, job title, the pain, how the company works, tech they use, business type, price point, geography, where the user spends time.
• Outbound data is a cleaner signal than leads from investors and friends.
• Signs you're close: conversion jumps, enthusiasm jumps, urgency to act now, and "the nod" of instant recognition.
• Examples: Gusto stacked six filters (tiny California companies, no benefits, salaried only); Gong sold only to US software companies selling over video in English.

Use it for: turning categories into three or more concrete attributes.

3. Rahul Vohra / Superhuman: measure it and segment by who loves you

Source: First Round Review, "How Superhuman built an engine to find product-market fit".

• Ask active users how they'd feel if they could no longer use the product. 40% "very disappointed" is the benchmark; about 40 responses is enough to be directional.
• Segment by the "very disappointed" group. Their roles and their own descriptions of who benefits become the ICP and the copy.
• Ignore the "not disappointed". Work on what fans love and what holds back near-fans who already get the main benefit.

Use it for: products with users. Suggest running the survey when the founder has 40+ active users.

4. April Dunford: start from the alternatives

Source: Obviously Awesome; aprildunford.com quickstart guide.

• Order: competitive alternatives → differentiated capabilities → value → who cares most about that value (the best-fit customer) → market category.
• Ask what customers would do if you didn't exist. "Hire someone", "do it ourselves" and "do nothing" are real competitors.
• The same product can win with a different customer: look at the few who use it wildly well and ask why.

Use it for: finding what the founder actually replaces, and anchoring price against it.

5. Rob Fitzpatrick: The Mom Test

• Talk about their life, not your idea. Ask about specific past behaviour, not hypothetical futures. Listen more than you talk.
• Compliments are noise. Commitments (time, money, an intro to the decision-maker) are signal.

Use it for: the founder's own customer conversations, and for judging the evidence they report to you.

6. Bob Moesta: the struggling moment

Source: Demand-Side Sales; Jobs to Be Done.

• Demand comes from a struggling moment, not a pitch. No struggle, no demand.
• Four forces: push of the current situation and pull of the new solution, against anxiety about the new and habit of the present.
• An ICP needs a trigger (when), not just firmographics (who).
• Weaker for impulse and consumer purchases, where the moment is fuzzier.

Use it for: the trigger question, and explaining lost "nice-to-have" deals.

7. Retool: hypotheses you kill, and language-market fit

Source: First Round Review, "Retool's path to product-market fit".

• Treat each ICP as a hypothesis and test it with cold outreach. Retool's first two guesses died fast; the third (developers at larger companies) worked.
• The words matter: the same product pitched in the customer's own language gets instant replies.
• Warm intros produce polite, vague meetings that fake fit.

Use it for: checking whether wins came only from warm relationships, and rewriting the pitch in customers' words.

How they combine

1. Guess three narrow attributes (Lenny), anchored on the alternative (Dunford) and the trigger (Moesta).
2. Test with cold outreach in the customer's words (Retool), using honest questions (Mom Test).
3. Measure and segment by who loves it (Vohra); confirm in-ICP customers retain and spend more (PostHog).
4. Narrow until it feels uncomfortable; expand only after winning that group.

Question bank

Ask one question per turn, in stage order. Skip anything already answered or found by looking it up. Each question lists the follow-up that matters most and the pattern to look for.

Stage 1: Paying customers

Q1. Who has actually paid you in the last 6–12 months, and roughly how much each? Real payments only, not pipeline. Rough numbers are fine.

• Follow-up if vague: "Start with the first one. What did you do for them, and did they pay?"
• Look for: concentration (one big customer), and whether revenue comes from one business line or several.

Q2. For each paying customer: what did you do, what result did they get, and how excited were they? Offer a simple scale: very excited (pushed to start, introduced others), polite interest, still deciding.

• Ask one customer per turn if there are several.
• Look for: what they actually bought (it's often narrower or different from what the founder thinks they sell).

Q3. Did they renew or buy again? If not, why not?

• Offer the usual reasons: one-off moment ended, no budget, the value wasn't measurable, their priorities changed, the fit was off.
• Look for: one-off vs ongoing value; whether the customer's own situation changed so what you sold stopped mattering to them.

Stage 2: Triggers and buyers

Q4. What was happening at each customer right before they bought? Prompt with examples: fresh funding, a launch, a key person leaving, expansion, a missed target, a competitor move.

• Look for: triggers that repeat across customers. These become the "when" of the ICP.

Q5. Which deals didn't close, and why?

• Look for: deals with no trigger ("nice-to-have"), price objections that are really urgency problems.

Q6. Who did you talk to in each deal, won and lost, and who approved the money?

• Look for: founder vs junior contact; whether wins needed a champion who could bring in the decision-maker. Lay won/lost against contact level in a small table.

Stage 3: Acquisition

Q7. How did each paying customer first find you, and what was the first small thing they did with you?

• Look for: the land-and-expand path (event, ticket, small project → bigger deal); warm vs cold; which content or channel created the first contact.

Q8. Has anyone come to you inbound from your content alone?

• Look for: whether content creates demand, or only builds trust after another first contact.

Stage 4: The second ICP (if the business has one)

Many businesses have two buyers: companies and individuals, or users and sponsors. Run this stage for the second one.

Q9. Have individuals paid for anything? How many, at what price, and who were they? Ask for the rough mix: roles, company types, experience levels.

Q10. What did they want out of it? A job, income, clients, a project, learning, status.

• Look for: the gap between the founder's stated promise and what buyers actually came for.

Q11. What happened to them afterward?

• Look for: outcome evidence. Without it, mark outcome claims as hypotheses and propose tracking.

Stage 5: Content

Q12. What content has actually worked: unusual reach, people at events, a buyer messaging you? What and where?

• Look for: personal vs brand accounts; social proof formats; which platforms have zero evidence (candidates to cut).

Stage 6: Goals and capacity

Q13. What does success look like in 90 days? Revenue, number of clients or customers, signups.

• Do the math out loud: implied conversion rates, deal counts, pipeline needed. Call out targets that need a conversion rate far above the evidence, and propose a realistic first milestone.

Q14. How many hours a week can the team realistically give this, and what's on the calendar that could get in the way?

Questions to use when the founder pushes back

• "The contact's seniority doesn't matter, right?" → Show the deal that stalled with a junior contact. The company is the market; the person who owns the budget is why it closes.
• "This is enough context, right?" → Say what's solid and name the two or three missing pieces (usually: who paid and renewed, the trigger, who approved the money).
• "Can't we just say X?" → Ask what evidence supports X today and what would prove it.

Things to never ask

• Anything you could look up.
• Leading questions ("Wouldn't you say your ICP is…?").
• Hypotheticals about future buying ("Would companies pay for…?"). Ask what already happened.

Report guide

The report has the sections below, in this order. Each one leads with its point in one sentence, then the table or list that proves it. Short sentences, real numbers, the founder's own names for things. Leave out any section the interview gave no material for.

Page structure

The ICP card is the hero and stays open, with a "This week" box (three tasks) beside it. Sections 2 to 9 are collapsed rows in the HTML. The row's summary line is the section's conclusion, so a founder who opens nothing still gets the findings. Section 10's checklist is the "This week" box; its open questions are the last row.

1. ICP card (required)

The first thing on the page and the part people will screenshot. One sentence that states the ICP, then five lines:

Every line must trace to evidence from the interview. If a line rests on a guess, write it and add "(to test)".

2. Goals

A small table: goal, target, where it stands today. Include the founder's stated target and, if you called it unrealistic, the realistic milestone next to it.

3. Evidence

The deals table: customer, what they are, who we spoke to, trigger, what we did, outcome, lesson. Newest or largest first. A second small table for the second ICP (programs, who came, price, result) if there is one. One line per row, no paragraphs inside cells.

4. Patterns

Three to five numbered findings, each one sentence plus the deal that proves it. These are the patterns named during the interview, now final. Example: "Deals closed in under 30 days when the owner was on the call; deals with only a manager took three times longer (three wins vs two stalls)."

5. Offer ladder

Entry → core → add-on, with price and purpose for each. Add pricing rules if the interview produced them (anchor, scope-for-discount, billing).

6. Sales plan

Pipeline math from the 90-day goal back to a target list size, with the close-rate assumption stated. Lead sources in priority order. The qualification checklist (one line per ICP field). An outreach template that opens with the trigger and proof from a real customer.

7. Second ICP and offer

Only if there is one: who they are, the positioning (proven claims only), what's in the offer, pricing, and outcome tracking.

8. Content plan

What content is for (its job in the sales motion), a table of channel / audience / what to post / cadence, and rules. Flag unproven channels with a review date.

9. Time and scorecard

Hours by area, calendar risks, and the weekly metrics with 90-day targets.

10. This week and open questions

Five to eight checkbox tasks for this week, then the open questions the interview couldn't settle.

Style rules

• Lead every section with its conclusion, never "This section describes…".
• Numbers with units and currency as the founder uses them ($4K, €300, $20/month).
• No adjectives standing in for evidence ("strong", "huge"). Show the number.
• Mark hypotheses as hypotheses.
• Keep the whole report readable in about five minutes.