Turn your top 5 objections into a spoken reply, an email reply, and a question back

What this does

You list the objections you hear. For each, the AI drafts a calm spoken reply, an email reply, and a question that helps you learn what’s behind it, without arguing or making claims you can’t back.

Who it’s for

AEs, SDRs, and owners who keep hearing the same pushback; managers building a team cheat sheet from real objections. Not for legal or contractual objections; escalate those.

What you need

• Your top 5 objections, in the buyer’s actual words
• Facts about your offer you can prove
• Anything you cannot promise (discounts, timelines)
• Tool: Any AI chat tool (for example ChatGPT, Claude, Gemini, or Grok), A notes doc for the final cheat sheet
• Cost: $0 with a free AI chat tier (limits change)
• Setup: 5 minutes (estimate)

Steps

1. Write your top 5 objections the way buyers actually say them. Add a fact you can prove for each if you have one.
2. List what you can’t promise (for example discounts or timelines).
3. Run the prompt.
4. Edit each reply until you’d say it naturally. Remove any claim you can’t prove.
5. Save the final five as a one-page cheat sheet and try one on your next call.

The prompt

You are a sales coach. For each objection below, write three things. Use ONLY the facts I provide about my product. Don't invent proof, customers, statistics, discounts, or guarantees. Where a fact would help but I didn't give one, write [ADD FACT].

NO-ADDITIONS RULE: Do not add facts, tips, statistics, scarcity or urgency, promises, references or testimonials, or the gender of any person that I did not supply.

What I sell: [PRODUCT, ONE SENTENCE]
Facts I can back up: [FACTS]
Things I cannot promise or offer: [LIMITS]
Objections, in the buyer's words:
1. [OBJECTION 1]
2. [OBJECTION 2]
3. [OBJECTION 3]
4. [OBJECTION 4]
5. [OBJECTION 5]

For each objection:
- WHAT IT OFTEN MEANS: 1-2 possible meanings (label as possibilities).
- LIVE REPLY: 2-3 spoken sentences. Acknowledge, don't argue, don't over-explain.
- EMAIL REPLY: under 90 words.
- QUESTION BACK: one open question that finds out what's really behind it.

Rules: Plain words. No pressure, no false urgency, no guilt. If the objection is valid for some buyers, say so honestly in the reply.

Sample input (fake data)

All names and companies are fictional. This is the input for run 4 (the output below), on the current prompt. Runs 5 and 6 used different inputs; see the test log.

What I sell: Online scheduling and invoicing tool for solo tutors
Facts: Plan is $19 a month; free 14-day trial (our pricing page); setup is guided in the app
Can't promise: Discounts, refunds beyond the trial, custom features
Objections: 1. "I can do this in a spreadsheet." 2. "It's too expensive for me." 3. "I don't have time to learn it." 4. "Do other tutors use it?" 5. "What if I want to cancel?"

Sample output

Real output from run 4 on 2026-10-14, using the current prompt, from an unspecified AI assistant (Grok Bot agent session; model name not shown). Copied as produced. Nothing was fixed after the fact; the problems we found in it are listed under “How it went”.

**1. "I can do this in a spreadsheet."**
- WHAT IT OFTEN MEANS: (a) the spreadsheet works well enough; (b) switching sounds like extra work.
- LIVE REPLY: "That's a fair option, and if it's working, that's good. If scheduling and invoicing ever feel like a lot, there's a free 14-day trial."
- EMAIL REPLY: A spreadsheet can work well. If scheduling and invoicing start to feel like a chore, there's a free 14-day trial at $19 a month after that, so you can see it without paying first.
- QUESTION BACK: "What does the spreadsheet do well, and where does it get awkward?"

**2. "It's too expensive for me."**
- WHAT IT OFTEN MEANS: (a) $19 a month is above their budget; (b) they can't yet see what they'd get.
- LIVE REPLY: "That's fair. It's $19 a month, and I can't offer discounts, but there's a free 14-day trial so you can see it first."
- EMAIL REPLY: Thanks for being straight with me. The plan is $19 a month and I can't offer discounts, but you can try it free for 14 days. If it's not worth it to you, that's okay.
- QUESTION BACK: "What would it need to do for you to feel the cost was worth it?"

**3. "I don't have time to learn it."**
- WHAT IT OFTEN MEANS: (a) they're busy; (b) they've had bad experiences with new tools.
- LIVE REPLY: "That makes sense. Setup is guided in the app. [ADD FACT: how long setup takes.]"
- EMAIL REPLY: Understood. Setup is guided in the app, so you're not left to figure it out alone. [ADD FACT: typical setup time.] The 14-day trial is free if you want to see how it feels.
- QUESTION BACK: "What's taking up most of your time right now?"

**4. "Do other tutors use it?"**
- WHAT IT OFTEN MEANS: (a) they want proof it works for people like them; (b) they don't want to be the first.
- LIVE REPLY: "Fair question. [ADD FACT: number or type of tutors using it, only if you can back it up.]"
- EMAIL REPLY: Fair question. [ADD FACT: how many tutors use it, or a reference, if you have one you can share.] I'd rather not guess, so the free 14-day trial is the simplest way to see for yourself.
- QUESTION BACK: "What would you want to see from other tutors to feel comfortable?"

**5. "What if I want to cancel?"**
- WHAT IT OFTEN MEANS: (a) they fear being locked in; (b) they're not sure they'll keep using it.
- LIVE REPLY: "Good thing to ask. [ADD FACT: how cancellation works.] You can try it free for 14 days first."
- EMAIL REPLY: Fair to ask before you sign up. [ADD FACT: how to cancel and any terms.] The 14-day trial is free, so you can try it before paying. I can't promise refunds beyond the trial.
- QUESTION BACK: "What would make you feel safe trying it?"

Check before you send

• Every product claim traces to the facts you gave. Remove or verify [ADD FACT] gaps.
• Replies don’t promise discounts, features, or timelines.
• The ‘question back’ is genuine curiosity, not a trap.
• Tone fits you and your buyer.

How it went

• Test date, tool, model: 2026-10-14. Unspecified AI assistant (Grok Bot agent session; the model name is not shown to the agent). One tool only.
• Runs logged: 6, on 6 different fake inputs (see the test log). Runs 1-3 used the original prompt. Runs 4-6 are a second round on new fake inputs after the prompt was fixed, as listed below. Every run was done by the same AI assistant session that wrote the fake input, and in round 2 the same session also edited the prompt, so these are not blind or independent runs. A script counted words and characters against the prompt’s limits. No second person re-ran it from the written steps.
• Why the label is “Tried in an AI tool,” not “tested”: we reserve “tested” for plays with at least 3 logged runs in at least 2 different AI tools, and we ran one tool. We also have no independent reproduction of the steps and no timed manual baseline. The runs are real, but this is one tool’s behavior, and 3 runs per round is too few to say a problem is gone.
• Time saved: Not measured. We did not time a manual baseline or an assisted run.
• What we changed after round 1: Added: no-additions rule only.
• Round 2 (current prompt, runs 4-6). What worked:
  • The invented items from the first round (company size, ‘$160 a month for a 40-person company’, ‘I’ll follow up next week’, ‘a good product’ about a competitor, a reference that doesn’t exist) did not appear in 15 replies this round.
  • When asked for proof that wasn’t supplied (run 4 ‘do other tutors use it?’) the model wrote [ADD FACT] and did not invent a count.
  • With no facts at all (run 5) the model produced placeholders rather than claims, and still gave usable question-back lines.
• Round 2: what failed or needed fixing:
  • Run 5 ‘That’s a common worry’ and run 5 ‘point you to the right option’ are small unsupplied claims. Run 6 says ‘Congratulations’ about a competitor contract. Small, but they are additions.
  • Run 4 reply 1 pairs a 14-day free trial with ‘$19 a month after that’; both facts were supplied but the ‘after that’ framing is the model’s.
  • 5 to 7 [ADD FACT] markers per output means the rep must supply real facts before anything is usable; with no facts (run 5) that is nearly everything.
  • 15 items per run to check against the fact list takes more than 2 minutes, so the edits column says No.
• Checked against “Check before you send”: ‘Every product claim traces to the facts you gave’ passed except for the small items listed; no reply promised a discount or timeline.
• Edge cases: No facts supplied (run 5): honest but mostly placeholders. Objections that invite proof (references, cancellation) were handled with [ADD FACT].
• Round 1 (original prompt, runs 1-3): what failed, kept for reference:
  • At least 4 of 15 replies went beyond the supplied facts: ‘$160 a month for a 40-person company’ (company size invented), ‘it’s a good product’ about a competitor, ‘I’ll follow up once next week’ (a promise), and ‘I’m glad to arrange a call’ with a reference that doesn’t exist.
  • One reply overreached the proof: ‘the switch isn’t big’ from ‘setup takes under an hour’.
  • Output is 15 items per run (3 per objection x 5). Checking every one against the fact list takes more than 2 minutes, so the edits column says No.
• Not yet observed: how a different model or tool handles the same prompt (a second-tool run is still to do).

Watch-outs

Email rules apply to the email replies (identity, honest subject, opt-out, postal address in the US). Don’t paste real customer names or contract terms into consumer AI tools unless your policy allows it.

See the Safe Use page: AI drafts, you decide, you send.

Variations

• Manager version: collect objections from the whole team; run the prompt once; review as a group for what reps disagree on.
• Owner version: add ‘what my competitors charge’ only if you know it for a fact.
• Price-focused version: a price-pushback play is planned.

Sources

None. Original wording. (Add any public framework or post used, with link and checked-on date.)

Retest

Re-check by: 2026-12-13 (60 days after the 2026-10-14 runs), or sooner when run in a second tool.

Test log

Changelog

• 2026-10-14: Draft written. Not run yet.
• 2026-10-14: Ran 3 times in one AI assistant on fake data. Filled in sample input and output, how it went, and the test log. Front matter set to runs_logged 3, last_tested 2026-10-14, retest_by 2026-12-13. The 2-tool bar for the word “tested” is not met, so the play is not labeled tested. The prompt text was not changed after the runs.
• 2026-10-14: Prompt revised after round 1. Added: no-additions rule only. Re-ran 3 fresh runs (4-6) on new fake inputs in the same AI assistant. Updated the sample input and output to run 4, the “How it went” section, and the test log (original runs 1-3 kept, marked). Front matter set to runs_logged 6, last_tested 2026-10-14, retest_by 2026-12-13. The 2-tool bar for the word “tested” is not met, so the play is not labeled tested.
• 2026-10-15: Published with the evidence label “Tried in an AI tool” (6 runs, 1 tool, fictional inputs). Earlier wording that implied more evidence than one tool’s runs was replaced with the label; the runs, results, and limits above are unchanged.