Milestone map
Milestone map
3 milestones
Map and document your current sales motion
1–2 weeks (5–8 hrs/week)
Write out every step a prospect takes from first contact to signed contract (or paid subscription). For each step, note: who does it, how long it takes, what information changes hands, and what causes prospects to drop off. Interview at least 3 recent customers about their buying journey — use their words, not your assumptions. The output is a documented sales process map, not a flowchart — it describes what actually happens, not what should happen.
Proof required
Submit your sales process map (can be a written document or annotated diagram) alongside 3 customer interview summaries that show where their account of the buying journey matches or differs from your map.
What gets checked
- Map distinguishes between steps you initiate and steps the prospect initiates — most early-stage founders miss prospect-side steps.
- At least one dropout point is identified with a specific reason (not 'lost interest') derived from customer interviews.
- Map covers the full journey from first awareness to money received — not just the sales call itself.
Common mistakes
- Mapping an ideal process rather than an observed one — common when the interviews weren't done before mapping.
- Treating every lost deal as 'wrong fit' rather than investigating whether it was a process failure.
- Stopping the map at 'closed won' — the handoff to onboarding is often where deals stall post-signature.
Powstik Guide
A map of every step from first contact to signed deal.
Steps
- List each step a prospect goes through.
- Note who does it and how long it takes.
- Mark where deals stall.
- Check the map in three customer interviews.
Template
| Step | Who | Typical time | Where deals stall | |------|-----|--------------|-------------------| Interview notes (3):
What gets sent back
- Steps with no owner or time.
- Fewer than three interviews.
- Stalls not identified.
Resources
Foundationstart here
What a verifier looks for
- Ask the founder where deals most commonly drop off — they should be able to name the specific stage and give a reason.
- Ask whether the map was built before or after the customer interviews — if before, the map may reflect wishful thinking.
- Ask what happens between 'verbal yes' and 'money received' — founders who can't describe this step have a process gap.
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Run 20 documented discovery calls
4–8 weeks (3–5 calls/week, plus documentation time)
Conduct 20 sales discovery calls with qualified prospects (not existing customers) using a consistent discovery script. Record or take structured notes from each call. After every call, complete a brief post-call note capturing: what problem the prospect described, what they're currently doing, what a win looks like for them, and your assessment of fit. Track stage progression after each call.
Proof required
Submit your discovery call script, 20 post-call notes in a consistent format, and a summary table showing each prospect's stage progression (discovery → demo → proposal → closed won/lost) with your conversion rate at each stage.
What gets checked
- Post-call notes capture the prospect's language, not just your assessment — direct quotes are present.
- Conversion rates are calculated from actual outcomes, not projected — some deals may still be open, which is fine, but state it.
- Discovery script includes open-ended questions about current solutions and switching costs, not just pain points.
Common mistakes
- Running 20 calls but documenting only a subset — the insight is in the pattern across all 20, not the memorable ones.
- Discovery calls that become product demos at the first sign of interest — this collapses the funnel and destroys insight.
- Conversion rate calculated from only the closed deals — pending deals distort the math and must be noted separately.
Powstik Guide
Twenty discovery calls using one script, with a summary table.
Steps
- Write a short discovery script.
- Book calls with qualified prospects only.
- Take notes in the same format each time.
- Summarise needs and next steps in a table.
Template
| # | Prospect | Pain | Budget | Decision maker | Next step | |---|----------|------|--------|----------------|-----------|
What gets sent back
- Existing customers counted.
- Fewer than 20 calls.
- Notes in different formats.
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the founder for the biggest pattern across the 20 calls — if they can't name one immediately, the post-call notes weren't systematic enough.
- Ask their current demo-to-close conversion rate — vague answers indicate the tracking wasn't maintained.
- Ask what one change they made to the script after the first 5 calls — if the script didn't evolve at all, it wasn't being used as a learning tool.
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Close 5 deals and write a repeatable sales playbook
8–16 weeks (ongoing alongside running the business)
Close at least 5 paid deals using your documented process. For each close, document what specifically moved the deal forward at each stage. Then write a one-document sales playbook covering: ICP definition, discovery script, objection responses (from actual objections in your 20 calls), proposal template, and close trigger. The playbook should be detailed enough for a future first sales hire to ramp on it.
Proof required
Submit evidence of 5 closed deals (contract signatures, payment records, or invoice confirmations — redacted is fine), your sales playbook document, and a one-paragraph note on which objection appeared most often and how you address it.
What gets checked
- Playbook objection section uses the exact phrasing customers used — not the founder's paraphrase of the objection.
- Close trigger in the playbook describes a specific signal (e.g. prospect asks about implementation timing, references a competitor by name) — not 'when they seem ready'.
- 5 closed deals are paid, not verbal commitments or pilots-in-progress.
Common mistakes
- Playbook written before the deals are closed — it describes a theoretical process, not an observed one.
- Objection section lists objections the founder anticipated, not the ones that actually came up.
- Counting POCs, pilots, or 'handshake agreements' as closed deals.
Powstik Guide
Five closed deals and a sales playbook someone else can run.
Steps
- For each deal, note what moved it at each stage.
- Save redacted signature or payment proof.
- Turn the common moves into playbook steps.
- Have someone else read it and ask questions.
Template
| Deal | Stage | What moved it forward | |------|-------|-----------------------| Playbook Stage 1: Goal: What to do: Exit criteria: Stage 2: Stage 3:
What gets sent back
- Fewer than five paid deals.
- A playbook with no exit criteria.
- No deal evidence.
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the founder to name the most common objection and walk through how they handle it — if their response doesn't match the playbook, the playbook wasn't built from real calls.
- Verify close triggers are specific and observable, not vague ('when they're ready').
- Ask what they would hand to a sales hire on their first day — if the answer isn't 'this playbook', the document isn't complete.
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