SimonTheSalesBooster Skill: Deal Progression Coach
What This Skill Does
Diagnoses a stuck or slow-moving deal and generates a specific action plan to unstick it. Asks the right questions to reveal hidden blockers, missing stakeholders, lack of urgency, or poor qualification — then prescribes the exact next move to progress the deal toward close.
When to Use
- A deal has been in the same stage for too long
- You don't know what to do next on a deal
- A prospect has gone quiet after a promising start
- You're preparing for a deal review and need to know your weak spots
- You want to coach a rep on a specific opportunity
Inputs Required
Before running this skill, ask the user to describe the deal in free text or structured format:
- Company name and deal size
- Current stage and how long it's been there
- What's happened so far — meetings held, content shared, people met
- What the prospect said last — their words, not your interpretation
- What you're currently waiting for / what the blocker seems to be
- Your next scheduled touchpoint (if any)
Step-by-Step Instructions
Step 1 — Deal Diagnostic Assessment
Evaluate the deal across 6 dimensions:
Dimension 1 — Champion Quality
- Is there a clearly identified internal champion? (Not just a contact — someone actively selling internally for you)
- When did you last hear from them? What are they doing to move this forward?
- Red flags: Champion has gone quiet, is only sharing info but not advocating
Dimension 2 — Economic Buyer Access
- Have you spoken directly with the person who controls the budget?
- Do they know the investment required?
- Red flags: Budget conversation hasn't happened, champion says "we'll handle it"
Dimension 3 — Urgency & Trigger
- Why does this deal need to happen now vs. in 6 months?
- Is there a business consequence to not solving this problem?
- Red flags: No defined business impact, no deadline tied to the problem
Dimension 4 — Decision Process
- Have you walked through the exact steps required to get a signed contract?
- Do you know who else needs to approve?
- Red flags: No mutual close plan, legal/procurement not yet scoped
Dimension 5 — Compelling Event
- Is there a date or event creating urgency? (Board meeting, product launch, end of budget cycle)
- Who owns that date?
- Red flags: Close date is arbitrary, driven by your quota, not their need
Dimension 6 — Competition & Alternatives
- Are there other solutions being evaluated?
- What's the "do nothing" alternative?
- Red flags: Prospect comparing you to a status quo they're comfortable with
Step 2 — Diagnose the Root Cause
Based on the assessment, identify the real blocker (often different from the apparent one):
| Apparent Blocker | Real Blocker | Fix |
|---|---|---|
| "Waiting on legal" | No economic buyer engaged | Get exec-to-exec meeting |
| "Evaluating options" | No differentiation established | Host a competitive bake-off call |
| "Timing isn't right" | No urgency / compelling event | Find or create a deadline |
| "Stakeholders need to align" | Champion is not actually a champion | Rebuild sponsor or find new one |
| "Budget not approved" | Deal was never properly qualified | Have the money conversation now |
| Prospect went silent | Deal is dead or stuck — needs direct conversation | Send the break-up email |
Step 3 — Generate the Next Move
Based on the diagnosis, prescribe one specific, high-leverage next action:
If champion is weak:
Send: "Hey [Name], I want to make sure we're setting this up for success. When we're ready to move forward, who else on your team would need to be involved in the decision? I want to make sure we have everyone's questions answered before we get to that point."
If economic buyer not engaged:
Ask champion: "At [Company], decisions like this typically involve finance or the [CEO/CFO/CRO]. Is [Name] already looped in, or should we plan to get them a summary?"
If urgency is missing:
Ask: "Help me understand — what's driving your timeline for solving this? Is there a specific date or initiative this needs to be in place for?"
If prospect went silent (10+ days):
Send the "Permission to Close?" email:
Subject: Permission to close your file?
Hey [Name],
I haven't heard back and I don't want to keep bothering you. If this is no longer a priority, that's totally fine — just let me know so I can close your file on my end.
If timing has just been off, I'm happy to pick this back up whenever works for you.
Either way — no hard feelings.
[Your name]
Step 4 — Build a Mutual Close Plan
If the deal is still live and qualified, co-create a mutual action plan:
MUTUAL CLOSE PLAN — [Company] ↔ [Your Company]
Target Start Date: [When they want to be live]
Target Contract Date: [Work backward 2–3 weeks from start]
Required Steps:
[ ] Security review — Owner: [Their IT] | ETA: [Date]
[ ] Legal review — Owner: [Their Legal + Our Legal] | ETA: [Date]
[ ] Executive sign-off — Owner: [Economic Buyer] | ETA: [Date]
[ ] Technical POC / pilot — Owner: [Their team + CS] | ETA: [Date]
[ ] Final proposal sent — Owner: [Your AE] | ETA: [Date]
[ ] Contract signed — Target: [Date]
Share this document with the prospect. Deals with mutual close plans close 2x faster.
Step 5 — Output the Deal Coaching Summary
DEAL COACHING SUMMARY
Deal: [Company] | $[Value] | Stage: [Stage] | Days in stage: [X]
ASSESSMENT:
Champion: [Strong / Weak / Unknown]
Economic Buyer: [Engaged / Not engaged / Unknown]
Urgency: [Present / Manufactured / None]
Decision process: [Mapped / Partial / Unknown]
Competition: [None / Named / Status quo]
ROOT CAUSE BLOCKER:
[One sentence diagnosis]
NEXT MOVE (do this TODAY):
[Specific action + message/email to send]
IF THAT DOESN'T WORK:
[Backup move or escalation path]
DEAL PROBABILITY:
[Revised close probability based on assessment] %
Output Format
Deliver:
- Deal Diagnostic Assessment (6-dimension scorecard)
- Root Cause Identification
- Next Move Prescription (specific message/action)
- Mutual Close Plan (if appropriate)
- Deal Coaching Summary card
Pro Tips
- The fastest way to unstick a deal is to have an honest conversation about what's really in the way — most reps avoid this because they fear the answer
- A "break-up email" closes more deals than most follow-up sequences — because it creates urgency and gives the prospect a guilt-free out, which many use to actually re-engage
- The mutual close plan is the single highest-leverage tool in late-stage selling — if a prospect won't co-create it with you, the deal is not as real as you think
- "What needs to happen for us to start on [date]?" is the most powerful question in sales — use it in every deal conversation
- Revisit deal health every 7–10 days — if nothing changes, something is wrong