Sales coaching is a $5 billion industry built on one simple truth: most people don't know what to say when money is on the line.
They freeze on calls. They fumble objections. They write DMs that sound desperate. And the deals that should have closed quietly disappear into "I'll get back to you" purgatory.
Here's the thing — the problem isn't talent. It's preparation. Every sales cycle has a handful of specific moments where deals live or die. Cold outreach that gets ignored. Price objections that stall conversations. Follow-ups that feel like nagging. Discovery calls that go nowhere.
These moments are predictable. And if they're predictable, they're fixable.
Below are 10 AI prompts — each one targeting a specific deal-killing moment in the sales cycle. They're not theoretical. They're structured to generate scripts, responses, and sequences you can use immediately.
Prompt 1: Cold DM Opener
Generic cold messages get ignored. Specificity gets replies. This prompt writes concise, personalized outreach that earns attention instead of blocks.
The prompt:
You are a world-class salesperson who writes concise, personalized cold messages that get 30%+ reply rates. Write a 3-4 line cold DM to [Prospect Name] at [Company]. They recently [specific trigger, e.g. posted about X, raised funding, hired for Y]. My product [brief 1-sentence description]. Make it curious, non-salesy, and end with a soft question.
What to feed it:
- Prospect name and company
- A recent trigger event (funding round, job post, social post)
- Your product in one sentence
Use this for LinkedIn, Twitter/X, or Instagram cold outreach. The key is the trigger event — it proves you did your homework and gives the AI something specific to anchor the message around.
Prompt 2: Value Proposition Tailor
Your pitch shouldn't sound the same to every prospect. This rewrites your core value prop for each specific person, using their pain points as the frame.
The prompt:
You are a top-tier sales consultant. Rewrite my core value prop for [Prospect Name] at [Company]. Their biggest pain is [pain 1], [pain 2]. My solution delivers [benefit 1], [benefit 2], [benefit 3]. Make it 2-3 sentences, benefit-focused, no fluff.
Generic pitches get generic responses. When you tailor the value prop to the specific pains a prospect cares about, you stop sounding like a brochure and start sounding like someone who gets it.
Prompt 3: The "Too Expensive" Handler
Price objections kill more deals than anything else. This prompt reframes cost as investment using your actual ROI numbers.
The prompt:
Role-play as the prospect who just said 'This seems really expensive.' Then write my response as a confident closer. Acknowledge the concern, reframe with ROI using these numbers: [insert your pricing + customer results]. End with a question that moves the conversation forward.
The role-play structure is deliberate. By having the AI voice the objection first, it generates a response that directly addresses the emotional weight behind "too expensive" — not just the logical argument.
Prompt 4: The "Need to Think About It" Handler
"I need to think about it" is rarely about thinking. It's a signal that something unspoken is blocking the decision. This prompt generates three different angles to surface what's really going on.
The prompt:
Prospect just said 'I need to think about it.' Write 3 possible replies (DM or call): One that creates gentle urgency. One that uncovers the real objection. One assumptive close. Keep each under 4 lines and natural.
Three replies gives you options. One might be right for a warm lead who needs a nudge. Another works better when you sense hesitation you can't name yet. Having all three means you're never caught off guard.
Prompt 5: The "Need to Talk to My Boss" Handler
When a prospect needs internal approval, the deal doesn't depend on your sales skills anymore — it depends on whether they can sell it internally. This prompt equips them to do that.
The prompt:
Prospect says they need to run it by their [partner/boss/team]. Write a response that: Offers to help them sell it internally. Provides social proof. Suggests next steps (e.g. forwardable summary or joint call). Make it collaborative, not pushy.
Instead of hoping they figure out how to pitch your product to their boss, give them the tools. A forwardable summary. Proof points they can reference. A suggested next step that keeps you in the loop.
Prompt 6: No-Response Follow-Up Sequence
80% of sales require 5+ follow-ups. Most people stop at 2. This builds a four-message sequence that adds value with each touch instead of just "checking in."
The prompt:
Create a 4-message follow-up sequence for a prospect who went dark after a strong demo. Spacing: Day 3, Day 7, Day 14, Day 21. Each message adds new value (case study, insight, question). Tone: helpful, low-pressure, curious.
The spacing matters. So does the value escalation. Each message should give the prospect a reason to re-engage — not guilt them into it. A case study on Day 7. A relevant insight on Day 14. By Day 21, a direct but respectful check-in.
Prompt 7: Discovery Questions
Bad discovery means bad close. This prompt generates questions that uncover budget, authority, need, and timeline naturally — plus two "implication" questions that amplify the pain.
The prompt:
Generate 8 powerful discovery questions for a [industry] prospect who [specific situation]. Questions should uncover budget, authority, need, timeline (BANT) naturally. Include 2 'implication' questions that amplify pain.
The implication questions are the secret weapon. They don't just ask about the problem — they make the prospect feel the cost of not solving it. That emotional weight is what moves people from "interested" to "ready."
Prompt 8: Assumptive Close Script
"Would you like to buy?" is a weak close. Assuming the sale and guiding the prospect to the next step is how confident closers operate.
The prompt:
Write a smooth assumptive close for the end of a call. We've covered [features discussed], they showed interest in [specific points]. Options: [your packages/pricing]. Make it conversational and include fallback if they hesitate.
The fallback is critical. If they hesitate, you need a natural pivot that keeps the conversation alive without making it awkward. This prompt builds both the close and the safety net.
Prompt 9: "Just Send Me Info" Deflector
"Can you just send me some info?" is a polite brush-off. This converts those info requests into actual conversations.
The prompt:
Prospect says 'Can you just send me some info?' Write a reply that: Politely pushes back. Books a 15-min call instead. Offers a personalized case study relevant to their company. Keep it short and confident.
The move here is strategic: acknowledge the request, offer something better (a personalized case study), and redirect toward a call. It's not about being pushy — it's about proving the conversation is worth their time.
Prompt 10: Negotiation Playbook
When they ask for a discount, the worst move is caving. This generates three negotiation responses using anchoring, value trading, and walk-away power.
The prompt:
Role-play a negotiation where they ask for [specific discount/custom terms]. Give me 3 strong responses using anchoring, trading value, and walking-away power.
Each strategy works differently. Anchoring resets expectations. Value trading says "I can move on price if you move on terms." Walk-away power reminds them that your offer has limits. Together, they give you a complete negotiation toolkit.
How to Use This System
These 10 prompts aren't random. They follow the sales cycle:
Prompts 1–2 handle cold outreach and personalized value props — the opening. Getting in the door with something specific enough to earn a reply.
Prompts 3–5 neutralize the three objections that kill most deals — price, indecision, and internal approval. These are the moments where "interested" turns into "lost."
Prompt 6 creates a follow-up sequence that adds value instead of nagging — because persistence without value is just noise.
Prompts 7–10 handle discovery, closing, deflection, and negotiation — the mechanics of turning a conversation into a commitment.
Each prompt works on its own. But used together, they cover every critical moment from first contact to signed deal.
The Difference Between a Prompt and a System
A single prompt gives you a single output. A system gives you consistent performance across every sales scenario you'll face this quarter.
That's the shift. It's not about finding the perfect words — it's about having structured responses ready for the moments that matter. The AI handles the generation. You handle the strategy. The deals stop dying in the gaps.
Explore the full system →
Frequently Asked Questions
### Do AI sales prompts actually work?
Yes — but only when they're specific. Generic prompts produce generic output that prospects ignore. AI-personalized cold outreach achieves up to 3x higher reply rates compared to templated messages, and the gap is widening. The difference is context: prompts that include prospect names, trigger events, specific pain points, and your actual product details force the AI to generate targeted responses instead of average ones. A well-structured prompt system consistently outperforms improvised scripts because it eliminates the guesswork at every stage of the sales cycle.
### What is the best AI prompt for cold DM outreach?
The highest-performing cold DM prompts include three elements: a specific trigger event (something the prospect recently did or said publicly), a one-sentence product description, and a soft closing question. The prompt should instruct the AI to be curious and non-salesy. For example: "Write a 3-4 line cold DM to [Name] at [Company]. They recently [trigger]. My product [description]. Make it curious and end with a soft question." This structure consistently outperforms generic "Hey, I'd love to connect" messages because it proves you did your homework before reaching out.
### How do you handle the "too expensive" objection using AI?
Use a role-play prompt that has the AI voice the objection first, then write your response. This approach works because it forces the AI to address the emotional weight behind the price concern — not just the logical argument. Feed the prompt your actual pricing and customer results (ROI numbers, time saved, revenue generated), and instruct it to reframe cost as investment. The strongest responses acknowledge the concern genuinely, anchor the price against the cost of inaction, and end with a forward-moving question rather than a defensive justification.
### How many follow-ups should you send after a sales demo?
Research shows 80% of sales require five or more follow-ups, yet most salespeople stop after two. The optimal cadence is Day 3, Day 7, Day 14, and Day 21 after the demo — with each message adding new value rather than just "checking in." Day 3 might reference something specific from the demo. Day 7 shares a relevant case study. Day 14 offers a new insight about their industry. Day 21 is a direct but respectful close-or-move-on check-in. The key is value escalation: every touch gives the prospect a reason to re-engage, not guilt.
### What are BANT discovery questions in sales?
BANT stands for Budget, Authority, Need, and Timeline — the four qualifying criteria that determine whether a prospect can actually buy. Effective BANT discovery questions don't ask these directly (nobody responds well to "What's your budget?"). Instead, they surface this information naturally through conversation. AI can generate questions like "What would solving this problem be worth to your team this quarter?" (budget), "Who else would need to sign off on a decision like this?" (authority), and "What happens if this doesn't get addressed in the next 90 days?" (need + timeline). The strongest discovery sets also include "implication questions" that amplify the pain of inaction.
### Can AI replace a sales coach?
AI can't replace a sales coach, but it can systematize what good coaches teach. A coach gives you frameworks — AI gives you the frameworks applied to your specific deal, prospect, and scenario in real time. The most effective approach is using AI to generate first-draft scripts, objection responses, and discovery questions tailored to each situation, then refining them with human judgment. Think of AI as the system that ensures you never walk into a sales conversation unprepared, while the coach helps you develop the instincts that no script can replace.
### How do you respond when a prospect says "just send me some info"?
"Send me info" is almost always a polite brush-off, not a genuine information request. The most effective response acknowledges the request, then offers something more valuable: a personalized case study relevant to their specific company or industry, paired with a suggestion to walk through it together in a 15-minute call. This works because it reframes the conversation from "let me evaluate your generic materials" to "let me show you something built for your situation." The key is confidence without pushiness — you're offering more value, not ignoring their request.
### What is an assumptive close and how do you use AI to write one?
An assumptive close skips "Would you like to buy?" and instead guides the prospect directly toward the next step as if the decision is already made. For example: "Based on what you shared about [their pain], the [package name] covers everything we discussed. I'll send the agreement over this afternoon — does that work for your timeline?" AI can generate these by feeding it the features discussed, the prospect's specific interest points, and your pricing options. The best assumptive close prompts also include a natural fallback if the prospect hesitates, so the conversation stays alive rather than hitting an awkward dead end.
