SimonTheSalesBooster Skill: Deal Closer Playbook
What This Skill Does
Guides a seller through the final stages of a deal with a sequenced closing system. Identifies the right closing technique for the specific situation, generates closing language, handles last-minute hesitation, and creates the moment of decision — without pressure, without manipulation, and without leaving money on the table.
When to Use
- A deal is in late stage and needs to be brought to a close
- You don't know how or when to ask for the business
- A prospect keeps saying "almost" or "just a bit more time"
- You've done everything right but the deal hasn't crossed the line
- You want to close faster without being pushy
Inputs Required
Before running this skill, ask the user for:
- Deal overview — company, size, stage, how long in pipeline
- What the prospect said last — their exact words, not your interpretation
- What's been agreed — scope, pricing, timeline, stakeholders aligned
- What's still unresolved — any open questions, concerns, or pending approvals
- Your desired close date — and why (is it real or arbitrary?)
Step-by-Step Instructions
Step 1 — Determine the Close Readiness Score
Evaluate if the deal is actually ready to close, or if closing pressure will backfire:
Close Readiness Checklist:
✓ Champion is actively engaged (not just responsive)
✓ Economic buyer has been in at least one conversation
✓ Budget has been confirmed (not just "we have budget")
✓ Decision criteria are clear and you've addressed them all
✓ Timeline is prospect-driven (not invented by you)
✓ Mutual close plan has been shared and accepted
✓ No unresolved objections (even unstated ones)
✓ Prospect has initiated next steps at least once
✓ Legal/procurement is scoped (if enterprise deal)
Score 7+ = Close now. Score 4–6 = Advance, don't close yet. Under 4 = You have qualification work to do.
Step 2 — Select the Right Closing Technique
Match the technique to the situation:
The Assumptive Close (Use when: all signals are positive, just need to lock in)
"Based on everything we've covered, I'd like to move forward. I'll send the agreement over today — does [signing contact name] need anything specific from me to turn this around quickly?"
The Summary Close (Use when: complex deal with many moving parts)
"Let me summarize where we are: we've agreed on [scope], at [price], starting [date], and [Name] will be the main contact. Does that capture everything accurately? If so, I'm ready to send the contract today."
The Date-Anchored Close (Use when: there's a real compelling event)
"To hit your [go-live date / board meeting / event], we'd need a signed agreement by [date]. That's [X days] from now. Are we in a position to move?"
The If/Then Close (Use when: prospect has one remaining condition)
"If we can [resolve their condition], is there anything else that would prevent you from moving forward? Great — let me see what I can do on that."
The Alternative Close (Use when: prospect needs to make a choice, not a yes/no)
"Would you prefer to start with [Option A] now and expand later, or go with [Option B] from the beginning?"
The Direct Close (Use when: relationship is strong and dancing is wasting time)
"[Name], I'll be direct — do we have a deal? What would it take to get this signed this week?"
Step 3 — Handle the "Just One More Thing" Pattern
When a prospect adds a new condition as you near the close:
Step 1 — Acknowledge without agreeing:
"I hear you — [condition]. Before we dig into that, help me understand: if we resolve this, are we ready to move forward?"
Step 2 — Identify if it's real or a delay tactic:
- If they say yes → Resolve it and close
- If they hedge → There's another real objection underneath — find it with: "What else is making you hesitant?"
Step 3 — Trade, don't give: Never resolve a late-stage condition without getting something back.
"I can [do X], but to make that work I'd need [contract signed by date / longer term / upfront payment]. Does that work for you?"
Step 4 — The Close Conversation Structure
Use this sequence in the closing meeting or call:
1. Summarize the journey (2 min):
"We've come a long way — [recap key milestones]. I feel like we're aligned."
2. Confirm the value (2 min):
"Based on what you told me about [their stated goal], you're expecting [outcome]. Is that still the target?"
3. Address any remaining concerns proactively (3 min):
"Is there anything we haven't addressed that's still on your mind?"
4. Make the ask (1 min):
[Choose technique from Step 2 based on situation]
5. Go silent:
After asking for the business — STOP TALKING. The first person to speak loses.
Wait 10–15 seconds minimum. Let the silence work for you.
Step 5 — Post-Close Momentum Moves
After they say yes:
Immediate (within 1 hour):
- Send a brief email: "Excited to get started. Contract coming over shortly."
- Send the agreement within the hour (don't let it cool)
- Cc the right people to signal momentum
Within 24 hours:
- Introduce the CSM or implementation contact
- Confirm kickoff date
- Remove any open questions that could create buyer's remorse
Buyer's Remorse Prevention:
"Congratulations — and I want to say, you made the right call. [Customer name] said the same thing when they started, and here's what happened: [brief outcome story]. You're going to see results within [timeframe]."
Step 6 — When They Say Not Yet
If the prospect says "not yet" or "give me more time":
The Pause and Learn:
"I respect that. Can I ask — what would need to be true for this to make sense in [30/60/90] days? I want to make sure we're using that time well."
The Graceful Re-Engagement: Schedule a specific follow-up with a defined reason:
"Let's talk again on [date]. By then, [specific trigger or milestone] should have happened — that'll give us a clearer picture. Does [specific time] work?"
Output Format
Deliver:
- Close Readiness Score (checklist + verdict)
- Recommended closing technique with ready-to-use language
- "One more thing" handler script
- Full closing conversation structure
- Post-close momentum actions
Pro Tips
- The close is a moment you create, not a conversation you have — it starts at the first meeting when you set the right expectations
- The biggest deal-killer in the close isn't the prospect's hesitation — it's the rep talking after asking for the business
- Never discount to close. Discounts signal that you were overcharging. Use terms (payment schedule, start date, add-ons) instead of price cuts.
- If a deal takes more than 3 close attempts, go back to qualification — you're closing the wrong deal
- The best close is when the prospect feels like they're making a smart business decision, not being "sold"