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Calibrated Questions Planner

by @quochungto

Generate a bank of open-ended strategic questions (how/what questions) for a negotiation, sales conversation, difficult discussion, or conflict situation. Us...

⚑ When to Use
TriggerAction
You want to ask questions that make the counterpart think and talk, rather than questions they can deflect with a yes or no. You need information without seeming demanding. You may also need to surface hidden stakeholders or deal-blocking issues before they derail the deal.
**Input this skill needs:** A situation brief (what the deal is, who is involved, what you know so far) and your goals. If you have a stakeholder map or conversation history, include them.
**Do not use this skill if:** You need to write a complete negotiation plan β€” use `negotiation-one-sheet-generator`. You need to handle an accusatory or hostile counterpart before questions can land β€” run `accusation-audit-generator` first to defuse the situation.
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πŸ’‘ Examples

Example 1: Enterprise Software Sales β€” Uncovering Hidden Budget Constraints

Scenario: An account executive is closing a $120K annual contract. The prospect's main contact (a VP of Operations) has been enthusiastic throughout three months of evaluation. Two days before the expected close, the VP says "we need a bit more time." The executive suspects a budget approval issue but has not confirmed it.

Trigger: "What questions should I ask to find out what's really going on without being pushy?"

Process:

  • Step 1: Gaps β€” unknown whether VP has budget authority, unknown who else must approve, unknown whether there's a competing priority or budget freeze
  • Step 2: Bucket A β€” "What does success look like for your organization if this goes live in Q1?"
  • Step 3: Bucket B β€” "What does your finance team or CFO need to see before something like this moves forward?" / "How on board are the colleagues who haven't been part of our conversations?"
  • Step 4: Bucket C β€” "What could get in the way of moving forward by end of quarter?" / "What would make this impossible to approve right now?"
  • Steps 5-6: Sequence β€” start with bucket A to rebuild rapport, then bucket B to surface the approval process, then bucket C to name the obstacle directly
  • Output: calibrated-questions.md with 6 questions across 3 groups, each with a follow-up label template. The bucket C question ("What would make this impossible to approve right now?") surfaces the budget freeze directly, allowing the executive to offer flexible payment terms rather than losing the deal.


    Example 2: Salary Negotiation β€” Discovering Real Constraints and Decision Structure

    Scenario: A candidate is negotiating a job offer. The recruiter has offered $115K. The candidate's target is $130K. The recruiter says "that's the top of the band." The candidate does not know whether this is a firm limit or an opening position, or who has authority to go above the band.

    Trigger: "How do I find out if there's any real flexibility without ruining the relationship?"

    Process:

  • Step 1: Gaps β€” unknown whether band is truly fixed or negotiable, unknown who has authority to approve exceptions, unknown what the full package looks like (equity, bonus, title)
  • Step 2: Bucket A β€” "What does the full compensation picture look like at this level?" / "How does the company think about the tradeoff between base and total compensation?"
  • Step 3: Bucket B β€” "What would need to happen for an exception to the band to be considered?" / "How does a decision like that typically get made?"
  • Step 4: Bucket C β€” "What would make this offer impossible to adjust?"
  • Steps 5-6: Sequence β€” open with bucket A (expands the conversation beyond base salary, may reveal equity or bonus levers), then bucket B to understand decision process, save bucket C as a last probe
  • Output: calibrated-questions.md with 5 questions. The bucket B question ("What would need to happen for an exception to be considered?") reveals that the hiring manager can approve exceptions with VP sign-off β€” and the recruiter offers to make that call.


    Example 3: Partnership Negotiation β€” Surfacing Deal-Killing Misalignment Early

    Scenario: A startup founder is negotiating a distribution partnership with a large retail chain. After two months of discussion, both sides appear aligned. The founder is about to present final terms and suspects there may be exclusivity requirements from the retailer's side that would conflict with other distribution agreements β€” but nothing has been said.

    Trigger: "Before I present final terms, what questions should I ask to make sure there are no surprises?"

    Process:

  • Step 1: Gaps β€” unknown whether retailer requires exclusivity, unknown who in the retailer's organization must approve the deal, unknown whether procurement or legal has different requirements than the business development contact
  • Step 2: Bucket A β€” "What does a successful partnership look like for your team 12 months from now?" / "What matters most to your organization in how this gets structured?"
  • Step 3: Bucket B β€” "Who else in your organization will be involved in finalizing this?" / "What does your legal or procurement team typically need to review?"
  • Step 4: Bucket C β€” "What would make this structure impossible for your side to agree to?" / "What concerns do you have that we haven't discussed?"
  • Steps 5-6: Sequence β€” start with bucket A to reinforce shared vision, move to bucket B to surface legal and procurement review (rather than discovering it after terms are presented), use bucket C to explicitly invite deal-killing issues to the surface now
  • Output: calibrated-questions.md with 6 questions. The bucket C question surfaces the retailer's exclusivity requirement before final terms are presented, allowing both sides to redesign the agreement structure rather than walking away after a failed close.


    πŸ“‹ Tips & Best Practices

    [Space for observations made during the conversation] ```


    View on ClawHub
    TERMINAL
    clawhub install bookforge-calibrated-questions-planner

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