The Business Owner's AI Playbook
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93 prompts

Sales

Find them. Convince them. Close them. Then again.

Prompt #101 Free preview

Ideal Sales Conversation Map

Reverse-engineer the exact conversation that closes your best deals.

Copy-and-paste prompt

Act as a senior B2B sales coach.

Offer: [What you sell]
ACV: [$]
Sales cycle: [Days/weeks]
Top objection you keep hearing: [Objection]

Map the 5-stage conversation that turns a cold prospect into a paying customer:
1. Hook (first 30 seconds)
2. Pain diagnosis (questions to ask)
3. Value framing (your 3-line pitch)
4. Objection neutralization (the exact reframe)
5. Close (the single question that asks for the sale)

Write what I literally say at each stage.
Pro tip
If you can't say your pitch in 3 sentences, you don't have a pitch — you have a hope.
Expected result
A repeatable conversation any rep on your team can run.

Prompt #102 Free preview

7-Touch Cold Outreach Sequence

Stop sending one email and giving up. Build a sequence that closes 5x more.

Copy-and-paste prompt

Act as a cold outreach expert.

ICP: [Who]
Offer: [What]
Specific result we deliver: [Outcome + timeframe]

Build a 7-touch sequence over 21 days:
- Touch 1 (Email, Day 1): pattern-interrupt subject + 60-word body
- Touch 2 (LinkedIn, Day 3): connection note
- Touch 3 (Email, Day 5): case study or proof point
- Touch 4 (Email, Day 9): different angle, different pain
- Touch 5 (LinkedIn voice note script, Day 12)
- Touch 6 (Email, Day 16): the "break-up" email
- Touch 7 (Email, Day 21): the resurrection email

Each email under 90 words. No "just checking in." Ever.
Pro tip
The break-up email gets more replies than touches 1-4 combined. Always include it.
Expected result
A sequence that books meetings while you sleep.

Prompt #103

Discovery Call Question Bank

Stop pitching on discovery calls. Diagnose. Then prescribe.

Act as a top enterprise AE.

We sell: [Offer]
To: [Buyer persona]

Give me 15 discovery questions organized in 4 buckets:
1. Situation (where are they now)
2. Pain (what's broken and what it costs)
3. Impact (who else suffers from this prob

Prompt #104

Objection Response Library

Have a perfect comeback ready for every objection — before it ever comes up.

Act as a sales objection-handling expert.

Offer: [What]
Price: [$]
Top 8 objections we hear (paste them, or list "Too expensive," "We're already using X," "Send me more info," "Bad timing," "Need to talk to the team," "We tried something s

Prompt #105

The 'No' That Becomes a Yes

Turn 30% of your lost deals into closed deals 60 days later.

Act as a sales follow-up strategist.

Lost deal context: [Why they said no]
Original offer: [What]

Write a 90-day nurture for prospects who said "no":
- Day 7: value email (no ask)
- Day 21: industry insight relevant to their pain
- Day 45

Prompt #106

High-Ticket Sales Page Skeleton

A 12-section structure that converts cold traffic into $1k+ buyers.

Act as a high-ticket direct response copywriter.

Product: [Offer]
Price: [$]
Dream outcome for buyer: [Result]
Biggest objection: [Objection]

Write a sales page outline with these 12 sections (give me the headline + 2 bullets for each):
1

Prompt #107

LinkedIn DM Opener That Doesn't Suck

Get a 25%+ reply rate on cold LinkedIn DMs.

Act as a LinkedIn outbound specialist.

ICP: [Who]
What I sell: [Offer]
Specific recent trigger to reference: [Funding, hiring, post they made, content they shared]

Write 5 cold DM variations, each under 60 words. Each must:
- Reference so

Prompt #108

Sales Demo That Closes

Stop showing features. Start solving problems on the call.

Act as a sales demo coach.

Product: [What it does]
Top 3 use cases buyers care about: [Use cases]
Average demo length: [Minutes]

Restructure my demo into this format:
1. Recap their pain (2 min — in their words)
2. Show the ONE feature th

Prompt #109

Pricing Conversation Script

Stop dropping price. Start defending it with confidence.

Act as a pricing strategist + sales coach.

Our price: [$]
Common reactions: [What you hear]

Give me:
1. The exact phrasing for delivering the price (tone, pause, what to do next)
2. 4 ways to anchor before stating price
3. 5 responses to 

Prompt #110

The 1-Page Sales Playbook

Onboard a new rep in 2 weeks, not 2 quarters.

Act as a head of sales building a startup playbook.

Company: [Name]
Offer: [What]
ICP: [Who]
Sales cycle: [Days]

Build a 1-page sales playbook covering:
- Who we sell to (ICP in 1 sentence)
- Who we DON'T sell to
- Top 3 pains we solve (i

Prompt #111

Cold Call Opening That Works in 2026

Get past the first 10 seconds — where 90% of calls die.

Act as a cold call expert.

ICP: [Who]
Offer: [What]
Specific pain we solve: [Pain]

Write 5 cold call openers, each under 20 seconds. Each must:
- Acknowledge it's a cold call (the pattern interrupt)
- State why I'm calling them specifical

Prompt #112

Win/Loss Interview Script

Learn why you really win and lose deals — straight from the buyer's mouth.

Act as a win/loss researcher.

I want to interview recent buyers (won) and prospects (lost).

Write me 2 separate 12-question scripts:

WON interviews:
- What were you really trying to solve?
- Who else did you evaluate?
- What almost stopp

Prompt #113

Account-Based Outbound Playbook

Stop spraying. Land 10 dream accounts this quarter.

Act as an ABM strategist.

Tier-1 target accounts (paste 10): [List]
Offer: [What]
Why these accounts: [Reason]

For each account, give me:
- 3 buyer personas to engage (titles)
- A specific recent trigger event (use search)
- A custom valu

Prompt #114

Multi-Threading Strategy

Stop pinning your deal on one person who might quit, ghost, or get fired.

Act as an enterprise sales strategist.

Deal context: [Account, size, single point of contact]
Buying committee in this org (typical): [Roles]

Build me a multi-threading plan:
1. Map the buying committee (decision maker, champion, blocker,

Prompt #115

The Mutual Action Plan (MAP)

Turn 'we'll get back to you' into a signed close date.

Act as a B2B sales operator.

Deal: [Account, ACV, target close date]
Steps remaining to close: [List]

Build a Mutual Action Plan I can send the buyer:
- Joint goals (theirs + ours)
- Every step from today to signature (with owner + date)

Prompt #116

Sales Email That Gets Replies

60-word emails that book meetings, not unsubscribes.

Act as a B2B copywriter.

Recipient: [Title, company]
Trigger / reason for outreach: [Specific event]
What we do for people like them: [Outcome]

Write 3 cold email variations. Rules:
- Subject line under 5 words
- Body under 75 words
- Fir

Prompt #117

Referral Request Script

The single highest-ROI sales activity — and 90% of reps skip it.

Act as a referral generation expert.

Customer types most likely to refer: [Happy power users]
What I sell: [Offer]

Give me:
1. The perfect moment to ask for a referral (signal to watch for)
2. The exact 3-sentence ask (in person, email, a

Prompt #118

The 5-Minute Close

When the buyer is ready, get out of their way.

Act as a closing specialist.

I'm at the point in the call where I think they're ready. Give me:
1. The signals they're ready to buy (verbal + behavioral)
2. The 3 best closing questions ("Based on what you've seen...")
3. How to handle "le

Prompt #119

Renewal & Expansion Playbook

80% of revenue lives after the first sale. Don't leave it on the table.

Act as a customer success-driven sales leader.

Avg customer value Yr 1: [$]
Net retention target: [%]
Top expansion paths: [Upgrade, seats, add-on, etc.]

Build a renewal playbook covering:
- The "renewal starts at day 1" onboarding moment

Prompt #120

Sales Forecast That Doesn't Lie

Stop reporting fantasy pipeline. Forecast like a CFO.

Act as a revenue operations expert.

Current pipeline (paste stages + values, or describe): [Pipeline]
Avg sales cycle: [Days]
Historical close rate by stage: [%]

Build me a weighted forecast model that:
- Weights deals by stage AND deal a

Prompt #121

Negotiation Concession Playbook

Give up things you don't care about. Never give up margin.

Act as a B2B negotiation expert.

Deal: [ACV, term, key terms in dispute]
What they're asking for: [Discount, terms, scope]

Build me a concession map:
- 5 things I can give that cost me little (longer term, case study, intro, etc.)
- 5 thi

Prompt #122

Sales Coaching 1:1 Template

Make every rep 30% better with one focused 30-min meeting per week.

Act as a VP of Sales.

Build me a weekly 1:1 template for coaching a rep:
- Pipeline review (5 min — top 3 deals only)
- Skill of the week (10 min — one thing, deep)
- Call review (10 min — review 1 recording together)
- Commitments + roadb

Prompt #123

Lead Qualification Scorecard

Stop wasting calls on people who'll never buy.

Act as a sales ops leader.

Offer: [What]
Ideal customer: [ICP]

Build a 10-point lead scoring model:
- 5 firmographic signals (industry, size, role, geo, budget)
- 5 behavioral signals (pages visited, content downloaded, frequency)
- Score

Prompt #124

Champion Enablement Pack

Arm your internal champion to sell for you when you're not in the room.

Act as a B2B sales enablement expert.

Deal: [Account, champion title]
Their internal stakeholders + concerns: [Roles + concerns]

Build a champion enablement pack:
1. 1-page business case (problem, solution, ROI, risks)
2. 5-slide internal

Prompt #125

RFP Response Strategy

Win the RFPs that are worth winning. Skip the rest.

Act as a sales strategist who's run 100+ RFPs.

RFP context: [Account, deal size, deadline, # competitors]

Tell me:
1. The 5 questions to answer before deciding to respond (or pass)
2. How to know if this RFP was "wired" for a competitor
3

Prompt #126

Sales Triggers Watchlist

Reach out the moment buyers are most likely to say yes.

Act as a B2B revenue intelligence analyst.

ICP: [Who]
What we solve: [Pain]

Give me a list of 15 trigger events to monitor — events that signal a prospect is now in-market:
- 5 hiring signals (specific roles/keywords)
- 5 company signals 

Prompt #127

Webinar-to-Sale Conversion Path

Turn 30% of webinar attendees into pipeline.

Act as a webinar funnel expert.

Webinar topic: [Topic]
Attendee ICP: [Who]
Offer: [What]

Build the full path:
1. The on-webinar pitch (5 min at minute 45)
2. The post-webinar email sent within 1 hour
3. The 5-touch follow-up over 14 days

Prompt #128

Stalled Deal Resurrection

One email that wakes up 15% of your dead pipeline.

Act as a sales recovery expert.

Stalled deal context: [Last touch, days dormant, original pain]

Write me 3 resurrection email variations:
1. The "permission to close your file" email
2. The "new development on our end" email (only if true

Prompt #129

Sales Compensation Plan Designer

Pay reps in a way that drives the behaviors you actually want.

Act as a sales compensation consultant.

Business model: [SaaS / agency / services]
Sales cycle: [Days]
Avg deal size: [$]
Annual quota target per rep: [$]

Design me a comp plan with:
- Base salary
- Variable commission structure (rate + a

Prompt #130

Outbound Persona Research Doc

Know your buyer better than they know themselves before the first touch.

Act as a buyer research expert.

Target persona: [Title, industry]

Build me a deep persona doc:
- Top 5 KPIs they're measured on
- Top 5 fears that keep them up at night
- The internal politics they navigate
- The vendors they trust (and d

Prompt #131

Sales Page A/B Test Roadmap

Systematic testing that compounds 2-5% lifts into 50%+ over a year.

Act as a CRO + sales page expert.

Current sales page URL or content: [Paste]
Current conversion rate: [%]
Monthly traffic: [#]

Give me a 12-month test roadmap, prioritized by impact:
1. Headline tests (5 variations to try)
2. Hero CTA tes

Prompt #132

Buyer Persona by Stage

Different message for different stages — that's the unlock.

Act as a B2B marketing-to-sales handoff specialist.

ICP: [Who]
Stages: Unaware → Problem-aware → Solution-aware → Vendor-aware → Decision

For each of the 5 stages, give me:
- What they're searching for
- What content moves them to the nex

Prompt #133

First 30 Days as a New AE

Make a new rep productive in 30 days, not 90.

Act as a sales onboarding designer.

Company: [Name]
Offer: [What]

Build a 30-day onboarding plan:
- Week 1: product + ICP + listen to 20 recorded calls
- Week 2: shadow 10 live calls + write your own pitch
- Week 3: run 5 discovery calls 

Prompt #134

The Trial-to-Paid Conversion Sequence

Turn 25% more free trials into paying customers.

Act as a product-led sales expert.

Product: [What]
Trial length: [Days]
Current trial → paid rate: [%]

Build a trial conversion sequence:
- Day 0: welcome + the "aha" action that drives activation
- Day 2: success email if activated / "st

Prompt #135

Sales Dashboard That Matters

Stop tracking 50 metrics. Track the 5 that predict revenue.

Act as a RevOps lead.

I want a one-screen sales dashboard:
- Pipeline coverage (target 3-4x quota)
- Stage conversion rates (find the leak)
- Average deal cycle (compare to last quarter)
- Top 3 reps by pipeline created, not just closed
- 

Prompt #136

Sales Meeting Agenda Template

Stop holding the same useless meeting every week.

Act as a sales operations leader.

Reframe my weekly sales team meeting into 45 min:
- 5 min: the number (where are we vs target)
- 10 min: 1 deal walkthrough (rotating rep)
- 10 min: 1 skill drill (role-play, objection, etc.)
- 10 min: pip

Prompt #137

Pricing Page Conversion Audit

Find the 3 things on your pricing page costing you 30% of sales.

Act as a SaaS pricing + CRO expert.

Pricing page URL or screenshot: [Paste]
Plans + prices: [List]

Audit:
1. Anchor pricing (is the highest plan visible first?)
2. Plan naming (are names value-based, not feature-based?)
3. Feature compari

Prompt #138

Top-of-Funnel Outreach Volume Calculator

Reverse-engineer the math from revenue target to daily activity.

Act as a sales operations analyst.

Revenue target: [$]
Avg deal size: [$]
Sales cycle: [Days]
Win rate from SQL: [%]
Reply rate on outreach: [%]
Meeting → SQL rate: [%]

Calculate:
- # deals needed to hit target
- # SQLs needed
- # meeting

Prompt #139

Sales Battle Card

Win against your top 3 competitors every single time.

Act as a competitive sales strategist.

Competitor: [Name]
Our offer: [What]

Build a battle card:
- Where they win (and how to flip those)
- Where they lose (and how to land hard)
- Common buyer concerns about them
- Trap-setting questions

Prompt #140

Quarterly Business Review (QBR) Template

Turn renewals into expansion with a 30-min meeting.

Act as a customer-led revenue strategist.

Account: [Name, ARR, tenure]

Build a 30-min QBR template:
- Slide 1: results delivered (specific outcomes + numbers)
- Slide 2: usage trends + adoption gaps
- Slide 3: their goals for next quarter

Prompt #141

Sales Email Subject Line Lab

20 subject lines tested into 1 that doubles your open rate.

Act as a B2B email copywriter.

Audience: [ICP]
Offer / angle: [Hook]

Give me 20 cold email subject line variations across these styles:
- Curiosity (5)
- Specific number / proof (5)
- Personalized (5)
- Question (5)

Each under 6 words. T

Prompt #142

Sales Onboarding Call Script

First call after the close — set expectations and lock in success.

Act as a customer success leader.

Product: [What]
Avg time-to-first-value: [Days]

Write me a 30-min onboarding call script:
1. Recap their goals (in their words) — 5 min
2. Define success at 30/60/90 days — 10 min
3. Walk through the acti

Prompt #143

Sales Hiring Scorecard

Hire reps who actually sell — not just interview well.

Act as a head of sales hiring AEs.

Role: [SDR / AE / AM]
Comp band: [$]

Build a hiring scorecard:
- 5 must-have skills with how to test each
- 3 culture/behavior fits with how to test each
- A role-play scenario + grading rubric
- A take-

Prompt #144

Sales Forecast Cleanup Script

Get your CRM honest in one Friday afternoon.

Act as a RevOps lead.

I want to run a 2-hour pipeline cleanup with my reps. Give me:
1. The exact 5 questions to ask about every open deal >$10k
2. The "if no activity in X days → mark as Y" rules
3. The "if next step isn't scheduled → mar

Prompt #145

Discount Approval Framework

Stop letting reps cave on price without a fight.

Act as a CRO setting discount policy.

Sell price: [$]
Margin: [%]

Build me a discount approval ladder:
- 0-10%: rep can offer if certain conditions met (list them)
- 10-20%: manager approval + trade required
- 20%+: VP approval + multi-ye

Prompt #146

Sales Demo Recording Review

Find the 1 fix that doubles your demo close rate.

Act as a sales coach reviewing a demo recording.

I'll describe (or paste transcript of) my demo: [Context]

Diagnose:
1. Who talked more — me or them? (target: 60% them)
2. Where did I pitch features instead of solving pain?
3. What discov

Prompt #147

LinkedIn Profile That Sells For You

Buyers research you before they reply. Make them want to.

Act as a personal branding strategist for sales pros.

Role: [Your title]
ICP: [Who you sell to]
Top result you deliver: [Outcome]

Rewrite my LinkedIn:
1. Headline (under 100 chars, value-first, not title-first)
2. About section (3 short p

Prompt #148

Sales Pitch Deck (10 slides max)

A deck that supports the conversation, not replaces it.

Act as a B2B pitch deck designer.

Product: [What]
Buyer: [Who]

Build a 10-slide pitch deck:
1. Their world today (the painful "before")
2. The cost of doing nothing
3. Why now (what changed)
4. The new way (your category)
5. How we delive

Prompt #149

Cold Calling Script for Founders

If you're the founder selling, here's the call that gets meetings.

Act as a founder-sold sales coach.

Product: [What]
ICP: [Who]
Reason this only you can sell right now: [Why]

Build a founder-led cold call script:
1. Open with your founder identity (it's an asset, not a hide)
2. The 1-sentence "why you s

Prompt #150

Sales Process Bottleneck Audit

Find the single stage costing you the most revenue.

Act as a sales operations consultant.

Pipeline stage conversion rates (paste): [%]
Avg time in each stage: [Days]

Diagnose:
1. The single stage with the biggest conversion drop (the leak)
2. The single stage with the longest average time 

Prompt #151

The 'Why Now' Trigger Email

The cold email angle 90% of reps never use.

Act as a B2B sales copywriter.

ICP: [Who]
Trigger event we can reference: [Specific recent event for the company]
What we do: [Offer]

Write a 75-word cold email built around the trigger:
- Subject: references the trigger
- Line 1: congrat

Prompt #152

Sales Voicemail That Gets Returned

30-second voicemail that doubles your callback rate.

Act as a cold-call expert.

Offer: [What]
ICP: [Who]

Write me a 30-second voicemail script:
- Open with their name + my name + company
- The 1-sentence reason I called (specific, intriguing)
- 2 dates/times I'll try them back (gives a reas

Prompt #153

The Personalized Loom Video Outreach

Pattern interrupt that books meetings when email + LinkedIn fail.

Act as a sales outreach expert.

Prospect: [Name, title, company]
Trigger: [Specific recent event]
Offer: [What we do]

Write me a 90-second Loom script:
- 5 seconds: their name + why I'm sending this video specifically to them
- 30 seconds

Prompt #154

B2B Referral Partnership Plan

Build a partner channel that generates pipeline for free.

Act as a partnerships lead.

Our offer: [What]
ICP: [Who]

Build a referral partnership program:
- 10 types of partners who serve our ICP (agencies, consultants, complementary SaaS)
- The pitch to recruit them (what's in it for them)
- The 

Prompt #155

Sales Stage Exit Criteria

Replace 'feelings' with facts at every pipeline stage.

Act as a sales ops leader.

Pipeline stages: [List]

Define exit criteria for each stage — the specific, observable conditions a deal must meet to advance:
- Stage 1 → 2: [Discovery completed, pain confirmed, budget signal]
- Stage 2 → 3: [

Prompt #156

The 'Land' Offer for Enterprise

Start small. Earn the right to expand. Bypass procurement.

Act as an enterprise sales strategist.

Full offer: [What, ACV]
Enterprise barrier we keep hitting: [Procurement / security / budget]

Design a "land" offer:
- A small, departmental version they can buy without procurement
- Price under the

Prompt #157

Sales Email Personalization at Scale

Send 100 emails that each feel hand-written. Without writing 100 emails.

Act as an outbound systems expert.

ICP: [Who]
Offer: [What]

Build a personalization framework:
- 5 data points to scrape per prospect (LinkedIn headline, recent post, company news, role tenure, mutual connection)
- A merge-tag-ready templ

Prompt #158

Customer Win Story Template

Capture wins in a format your sales team will actually use.

Act as a marketing-sales alignment lead.

Build me a 1-page customer win story template:
- Customer name, industry, size
- The problem (in their words)
- Why they chose us (vs alternatives)
- The implementation (timeline + lift)
- The resul

Prompt #159

Sales Velocity Calculator

One number that tells you exactly how to grow revenue faster.

Act as a RevOps analyst.

Plug in:
- # of opportunities in pipeline: [#]
- Avg deal size: [$]
- Win rate: [%]
- Avg sales cycle: [Days]

Compute sales velocity = (Opps × ACV × Win rate) / Cycle.

Then show me the 4 levers to pull and how a 

Prompt #160

The 'Procurement' Survival Guide

Get your deal through procurement without losing months or margin.

Act as an enterprise sales leader.

Deal: [Account, size, expected procurement timeline]

Build me a procurement playbook:
- The 5 docs to prep BEFORE procurement gets involved (security, SOC 2, MSA, DPA, references)
- How to position my ch

Prompt #161

Sales Enablement Library

One Notion page that contains every asset a rep needs to close.

Act as a head of revenue enablement.

Build a Sales Enablement Library outline. List the categories and what goes in each:
1. Positioning + messaging
2. ICP + persona docs
3. Pitch decks (by use case)
4. Demo scripts + recordings
5. Case st

Prompt #162

The Pre-Call Research Routine

15 minutes of prep that doubles your discovery quality.

Act as a top-performing AE.

Build me a 15-min pre-call prep checklist:
- 2 min: LinkedIn — title, tenure, mutual connections, recent posts
- 3 min: Company — recent news, funding, hires, layoffs
- 3 min: Their content — what have they post

Prompt #163

Sales Pipeline Hygiene SOP

Weekly 30-min ritual that keeps your forecast clean.

Act as a RevOps lead.

Build a weekly pipeline hygiene SOP for reps:
- Every open opp: confirmed next step in calendar? (Y/N)
- Stage matches reality? (Y/N — if N, fix)
- Stuck >2x avg cycle in same stage? (Y/N — if Y, action plan)
- Multi-

Prompt #164

First Sales Hire Profile

Hiring rep #1? Get it right or set the company back 6 months.

Act as a founder-stage sales advisor.

Stage: [Pre / post product-market fit]
Avg deal size: [$]
Sales motion: [Inbound / outbound / blend]

Profile the right first sales hire:
- Title + level (don't over-hire — no VP Sales at $1M ARR)
- 5 

Prompt #165

Sales Activity Audit

Track inputs, not just outcomes — find the leverage point.

Act as a sales ops analyst.

Reps' activity data: [Calls, emails, LinkedIn touches, meetings booked, deals created]

Audit:
- Top rep vs average rep — what's different in activity volume + quality?
- Which activity correlates most with deal

Prompt #166

Cold Email A/B Test Plan

Improve cold email reply rates by 50% in 4 weeks.

Act as a cold outbound expert.

Current cold email + reply rate: [Paste + %]

Build a 4-week A/B test plan:
- Week 1: subject line (5 variations)
- Week 2: opener line (5 variations)
- Week 3: CTA (low-friction vs direct, 3 variations)
- We

Prompt #167

The Sales/CS Handoff SOP

Stop letting hard-won deals die in the first 30 days.

Act as a customer success lead.

Build a sales-to-CS handoff SOP:
- Required fields in the handoff doc: business goals, success metrics, stakeholders, risks, expansion paths
- The 3-way kickoff call (Sales + CS + Customer) within 5 days of 

Prompt #168

The 'Reactivation' Campaign

Wake up dead leads from 6+ months ago.

Act as a marketing-sales lead recovery expert.

Dead lead list context: [Source, age, last activity]

Build a 5-email reactivation campaign over 3 weeks:
- Email 1: "Are you still trying to solve X?" (the original pain)
- Email 2: A new res

Prompt #169

The 1-Slide Internal Champion Deck

One slide that lets your champion get internal buy-in for you.

Act as an enterprise sales strategist.

Deal: [Account, ACV, key stakeholders]

Build a 1-slide internal business case for my champion:
- Problem (in their CFO's language)
- Solution (1 sentence)
- Quantified impact ($ or % saved/earned, wi

Prompt #170

Sales Hiring Interview Questions

12 questions that reveal who actually sells vs who just talks well.

Act as a sales leader who's hired 100+ reps.

Give me 12 interview questions ranked by signal:
- 3 questions about their last deal (won + lost) — tests deal IQ
- 3 questions about their process — tests rigor
- 3 questions about a tough obje

Prompt #171

Customer Renewal Save Play

60-day playbook to save an at-risk renewal.

Act as a CS leader.

Account: [Name, ARR, risk signals]

Build a 60-day save play:
- Days 1-5: diagnostic call with champion (understand the real issue)
- Days 6-15: address top 1-2 issues with visible action
- Days 16-30: exec sponsor call

Prompt #172

Pricing Anchor Strategy

Make your real price feel like a bargain before it ever shows up.

Act as a pricing psychology expert.

Real price: [$]
Buyer's current alternative spend: [$ — internal team, competitor, doing nothing cost]

Build the anchoring sequence:
1. First anchor: the cost of doing nothing (status quo bias buster)
2

Prompt #173

The 'Show Don't Tell' Sales Asset

Replace your pitch deck with a 5-minute interactive demo.

Act as a product-led sales designer.

Product: [What]
Top use case to demo: [Use case]

Design a 5-minute self-serve demo asset:
- A clickable Storylane / Arcade walkthrough OR
- A sandbox login with pre-loaded data
- 3 "aha moments" highli

Prompt #174

Sales Email Template Library

20 templates your team can grab and personalize in 2 minutes.

Act as a sales enablement leader.

Build a 20-template library:
- 5 cold outreach (different angles)
- 5 follow-ups (different scenarios)
- 3 break-up emails
- 3 referral asks
- 2 renewal nudges
- 2 expansion conversation starters

Each tem

Prompt #175

The 'Champion Loss' Insurance Plan

When your champion quits or gets fired, your deal usually dies. Stop that.

Act as an enterprise sales strategist.

Deal: [Account, champion title, deal size]

Build a champion-loss insurance plan:
- 3 backup champions to develop in the same account (different functions)
- The "intro me to your boss" play before th

Prompt #176

Sales Cadence Optimizer

Design the perfect mix of touches across email, phone, LinkedIn, and video.

Act as a sales engagement expert.

Persona: [Who]
Avg deal size: [$]

Design a 14-touch cadence over 21 days, mixing:
- Cold emails (different angles)
- LinkedIn connection + DM
- Phone calls (with VM scripts)
- Video messages
- Social enga

Prompt #177

First Customer Acquisition Playbook (0 to 10)

From zero customers to your first 10 paying users.

Act as a founder-stage GTM advisor.

Product: [What]
Avg price point: [$]

Build my 0→10 customer playbook:
1. The 50-person list of "people who would obviously buy" (warm network, communities, past colleagues)
2. The 1:1 outreach script fo

Prompt #178

Account Plan for Strategic Deals

A 1-page plan that turns a $50k deal into a $500k account.

Act as a strategic account manager.

Account: [Name, current ARR, expansion potential]

Build a strategic account plan:
- Org chart with current relationships + gaps
- Their stated business priorities (from earnings call / annual report)
- 

Prompt #179

Sales Compensation Benchmark

Pay reps competitively or lose them to the competitor that does.

Act as a sales comp consultant.

Role: [SDR / AE / AM]
Industry: [Software / services]
Region: [US / EU / etc.]
Avg deal size: [$]

Give me:
- 50th / 75th / 90th percentile base + OTE for this role
- The typical commission rate (% of ACV)
-

Prompt #180

The 1:1 Sales Coaching Question Bank

20 questions that turn 1:1s from status updates into skill-building.

Act as a sales VP.

Give me 20 coaching questions, organized into:
- Pipeline questions (5)
- Skill development questions (5)
- Career growth questions (5)
- Reflection / self-coaching questions (5)

For each: when to ask it and the listeni

Prompt #181

Sales Deal Review Template

A 15-minute deep dive on 1 deal that improves the whole team's skill.

Act as a sales coach running deal reviews.

Build me a 15-min deal review template:
1. Account snapshot (1 min)
2. Pain + impact in customer's words (2 min)
3. Decision criteria + process (3 min)
4. Champion + multi-threading (2 min)
5. Ris

Prompt #182

Sales Productivity Audit

Find the 10 hours per rep per week being burned on garbage.

Act as a sales ops consultant.

Audit my reps' weekly time. Categorize hours into:
- Selling (calls, demos, follow-up)
- Prospecting (research, outbound)
- Admin (CRM updates, internal meetings)
- Learning (training, coaching)
- Wasted (dup

Prompt #183

The 'Best Lead Source' Audit

Stop spending on channels that don't close. Double down on what does.

Act as a marketing-sales attribution expert.

Lead sources we use: [List]
Cost per source: [$]

Build me a per-source ROI report:
- Volume of leads
- Cost per lead
- Lead → meeting rate
- Meeting → SQL rate
- SQL → close rate
- ACV by sourc

Prompt #184

AI-Powered Lead Research Workflow

Use AI to do 5 hours of research in 15 minutes.

Act as an AI-augmented sales engineer.

ICP: [Who]
Outreach goal: [Meeting]

Build me an AI-powered research workflow:
1. Pull from LinkedIn Sales Nav: titles, tenure, posts
2. Pull from company site / press: news, funding, hiring
3. Pull f

Prompt #185

High-Stakes Negotiation Prep

Walk into the biggest deal of the year with a plan, not a hope.

Act as an enterprise negotiation expert.

Deal: [Account, ACV, key sticking points]
Their must-haves: [List]
Our must-haves: [List]

Prep me:
- My BATNA (best alternative to no deal)
- Their BATNA (what's their next-best option)
- 5 zones o

Prompt #186

The Onboarding 'Aha' Engineering

Engineer the first wow moment in the first 24 hours.

Act as a product-led growth strategist.

Product: [What]
Current time to first 'aha' moment: [Hours/days]

Engineer faster aha:
1. Identify the single 'aha' action (the thing that, once done, makes them 5x more likely to convert)
2. Cut eve

Prompt #187

Late-Stage Deal Acceleration

Push a stuck Q-end deal across the finish line without discounting.

Act as a closing specialist.

Deal: [Account, ACV, where it's stuck]
Days until quarter-end: [#]
Last activity: [When]

Build me an acceleration plan:
1. The exec-to-exec call (theirs + ours)
2. The "incentive without discount" offers (free

Prompt #188

Sales Training Curriculum (90 days)

Turn a ramping rep into a quota-crusher in 90 days.

Act as a sales enablement lead.

Build a 90-day rep ramp curriculum:
- Days 1-30: product mastery, ICP, listen to recorded calls (deliverables + tests)
- Days 31-60: shadow + co-sell, write own pitch, run discoveries (deliverables + tests)

Prompt #189

The 'Annual Plan' Discount Lever

Trade a small discount for 12 months of locked revenue.

Act as a SaaS pricing strategist.

Monthly price: [$]
Current annual discount: [%]

Build me the annual upsell conversation:
1. The math (show them the savings in dollars, not %)
2. The 3 non-monetary reasons to commit annually (lock-in pri

Prompt #190

The 'Trial Ended' Last-Chance Email

Recover 10% of expired trials with one well-timed email.

Act as a SaaS lifecycle copywriter.

Trial product: [What]
Trial length: [Days]
Common reason trials lapse: [Reason]

Write me a 3-email "trial expired" save sequence:
- Day +1: "your trial ended — here's what you'd lose"
- Day +3: a custom

Prompt #191

Sales Hiring Take-Home Assignment

A 60-min assignment that reveals real sales chops.

Act as a head of sales designing a hiring assessment.

Build a 60-min take-home assignment for AE candidates:
1. Research a real (named) target account (15 min)
2. Write a 75-word cold email to a specific persona at that account (15 min)
3.

Prompt #192

The 'Free Strategy Call' Funnel

Turn a free call into a paying client without sleazy high-pressure tactics.

Act as a high-ticket coach / consultant.

Offer: [$X package]
ICP: [Who]

Build a 6-step funnel from cold to client:
1. Lead magnet (the free thing that attracts ICP only)
2. Application form (5 questions that disqualify time-wasters)
3. Pr

Prompt #193

The Sales Org of 5 Playbook

Structure your first sales team for max output, min management.

Act as a CRO building a 5-person sales org.

Build the org:
- 1 sales leader (player-coach)
- 2 AEs (1 hunter, 1 farmer)
- 1 SDR (outbound)
- 1 sales ops / RevOps

Define for each:
- Comp + OTE
- KPIs + targets
- Weekly cadence (1:1s, pipel

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