Sales Coaching

Sales Coaching

Overview

Coaching is the highest-leverage activity in a revenue org — and the most often skipped. Managers who "coach" by asking "how's the pipeline?" get fiction. Managers who inspect evidence (MEDDICC scores, call recordings, SPICED fields) change behavior.

Jacco van der Kooij (Winning by Design) built REKS so managers diagnose before prescribing: a rep missing quota might need effort discipline, product knowledge, or conversation skill — three different interventions. Late-stage stalls need JOLT (Dixon/McKenna), not more ROI slides.

This skill is the coaching operating system: cadence, diagnostics, deal reviews, call rubrics, 1:1 agendas, founder-as-coach, and manager calibration.

Process design → pipeline-management. Hard conversations / PIP → gtm-leadership. Onboarding ramp → revenue-team-onboarding.

When to Use

• "Build sales coaching program"
• "How do I coach my AEs / SDRs?"
• "Deal review format for managers"
• "1:1 template for sales manager"
• "Coach discovery calls"
• "Rep stuck — REKS diagnosis"
• "Coach late-stage indecision"
• "Founder coaching first sales hire"
• "Call coaching rubric"

Authoritative Foundations

• Jacco van der Kooij / Winning by Design — REKS. Results → Efforts → Knowledge → Skills. Coach the layer, not the number. SPICED for discovery coaching; Bowtie for handoff quality.
• Andy Whyte — MEDDICC. 0/1/2 scorecard (max 14). Managers inspect evidence per dimension — same gates as pipeline-management.
• Matthew Dixon & Ted McKenna — JOLT. Judge indecision → Offer recommendation → Limit exploration → Take risk off table. Coach when fit exists but buyer stalls.
• Kevin Dorsey. Daily manager rhythm during ramp; pipeline accountability without micromanagement; coaching as leadership core competency.
• Jon Barrows (Sell Better). Short-cycle skill reps for discovery, demo structure, objection handling — coach behaviors in 15-min drills.
• Jason Bay — PVP. Coach outbound relevance (Permissionless Value Proposition), not volume — for SDR/BDR coaching.
• Keith Rosen. Accountability coaching: commitments, timelines, ownership.
• Kim Scott. Radical Candor for performance — separate coaching from status.
• Randy Seidl (Sales Community). Three Plays — sell yourself, company/product, customer outcome. Relationship map + decision map for enterprise deals. Coach behaviors (trust-building touches, extended team usage) over pipeline fiction. Load references/randy-seidl-relationship-selling.md.
• Tom Slocum (The SD Lab). Sell the Meeting (nurse, not doctor); 3×3 research before call blocks; dial discipline and SDR intensives. Coach prep quality and conversation structure — not dial volume. Phone SDRs only (not email PVP). → references/tom-slocum-cold-calling.md
• Ryan Reisert (CallBlitz, Outbound Operators). CRM Activity Buckets for daily rep prioritization; CallBlitz live floor for peer/manager call coaching; completions-over-dials accountability. Pair with Slocum for skill; with Gilkey dispositions for list diagnosis. → references/ryan-reisert-cold-calling.md

Step-by-Step Process

Phase 1 — Coaching Stack (Load Order)

1. pipeline-management     → stages, MEDDICC gates, SPICED fields
2. sales-enablement        → playbook reps should execute
3. sales-coaching (this)   → diagnose + inspect + practice
4. buyer-indecision          → JOLT when late-stage stall
5. gtm-leadership          → if coaching fails → PIP / exit

Phase 2 — REKS Diagnosis (Before Any Coaching)

Load references/reks-diagnostic.md + templates/reks-diagnostic.md.

Rule: If E+K+S are adequate and Results still fail → territory, quota, or fit (gtm-leadership).

Phase 3 — Manager Cadence (Kevin Dorsey + WbD)

1:1 rule: No status updates — CRM holds status. 1:1 = development.

Phase 4 — Deal Review (MEDDICC)

Load references/deal-review-guide.md.

1. Rep presents scorecard (0/1/2 per dimension) — not narrative
2. Manager asks for evidence per score of 2
3. Identify gaps blocking next stage gate
4. One action per gap: owner, date, next step
5. Forecast category only if score ≥ gate (pipeline-management)

Coaching questions (Whyte):

• "Whose numbers are in Metrics — buyer's or ours?"
• "When did you last speak to the Economic Buyer directly?"
• "Does Champion pass all four tests — show me proof."
• "What's the Decision Process step and date?"

Phase 5 — SPICED Coaching (Discovery)

When rep struggles before MEDDICC is populated:

Phase 6 — JOLT Coaching (Late Stage)

When MEDDICC ≥ gate but deal stalls — load references/jolt-coaching.md + buyer-indecision.

Do not coach "send another ROI deck" for indecision — it increases FOMU.

Phase 7 — Call Coaching

Load references/call-coaching-rubric.md.

Per call (15-min manager review):

1. Listen at 1.25× — note timestamps
2. Score: discovery, value, objection, next step (1–5)
3. One keep — reinforce
4. One fix — specific behavior next call
5. Rep re-records 2-min role-play before next live call

SDR calls (phone): Coach 3×3 prep + sell-the-meeting (Slocum), pattern-interrupt opener + tonality (Pessar), CRM bucket discipline (Reisert). Live review via CallBlitz when available. Disposition distribution after 50 completions (Gilkey).

SDR outreach (email/LinkedIn): Coach PVP and relevance (Jason Bay), not dial count.

Phase 8 — Founder-as-Coach

Before first manager hire, founder coaches directly (references/founder-coaching.md):

Founder trap: doing deals instead of inspecting deals. Calendar-block coaching.

Phase 9 — 30-Day Coaching Plan (Underperformer)

Template: templates/coaching-plan-30-day.md

Week 1: REKS diagnose + enablement gap analysis
Week 2: Daily call review + skill drill
Week 3: Deal inspection cadence + accountability
Week 4: Measure leading indicators — if flat, escalate gtm-leadership

Output Format

Run scripts/check-output.py before delivery.

Quality Check

• REKS layer identified before coaching action
• Deal reviews use MEDDICC evidence — not rep confidence
• 1:1 agenda excludes status updates
• Call coaching: one keep + one fix per session
• JOLT used for indecision — not more collateral
• SPICED coached for discovery gaps
• Founder/manager cadence appropriate to team size
• Phone SDR coaching uses Slocum/Reisert — email SDR coaching uses Bay PVP
• Cross-ref pipeline-management stage gates

Common Pitfalls

1. Coaching results, not behaviors. "Hit quota" isn't coaching. Fix: REKS layer + one skill.
2. Skipping diagnosis. More dials for a knowledge gap. Fix: REKS first.
3. Deal review as storytelling. Fix: scorecard + evidence.
4. 1:1 as pipeline readout. Fix: CRM for status; 1:1 for development.
5. ROI pile-on for indecision. Fix: JOLT — recommendation + risk removal.
6. Founder stops coaching after hire #1. Fix: meta-coach the manager.

Execution Artifacts

| ../../outbound/cold-calling/references/framework-notes.md | Phone coaching framework anchors | | templates/output-template.md | Deliverable structure | | scripts/check-output.py | Validator |

Related Skills

• pipeline-management — MEDDICC gates, SPICED fields, stage design
• meeting-prep — SPICED questions reps should master
• buyer-indecision — JOLT playbook for reps
• sales-enablement — Collateral coaching references
• gtm-leadership — PIP, fire, Radical Candor
• team-management — OKRs, general 1:1s
• cold-calling — SDR phone motion, dispositions, call structure
• revenue-team-onboarding — Ramp coaching first 90 days
• demo-scripts — Demo coaching content
• objection-handling — Objection drills