sales-coaching

What this skill does

# Sales Coaching & Training

Help the user build coaching programs, onboard new reps, run role-plays, design certification paths, and measure coaching impact. This skill is tool-agnostic and applies to any enablement platform (Seismic Learning, Allego, MindTickle, SalesHood, Brainshark), conversation intelligence tool (Gong, Chorus, Observe.AI), or manual approach.

## Step 1 — Gather context


If `references/learnings.md` exists, read it first for accumulated knowledge.

Ask the user:

1. **What do you need?**
   - A) Build a new rep onboarding program
   - B) Create a coaching framework for managers
   - C) Design role-play/practice exercises
   - D) Build certification or skill assessment paths
   - E) Improve ramp time for new hires
   - F) Measure coaching effectiveness
   - G) Other

2. **Team size and structure?**
   - A) Small team (<10 reps, player-coach manager)
   - B) Mid-size (10-50 reps, dedicated managers)
   - C) Large (50-200, enablement team)
   - D) Enterprise (200+, enablement org)

3. **Current coaching tools?**
   - A) Seismic Learning
   - B) Allego
   - C) Gong/Chorus (conversation intelligence)
   - D) MindTickle
   - E) Brainshark
   - F) SalesHood
   - G) LMS (generic)
   - H) Spreadsheets/manual
   - I) Nothing formal

4. **Sales methodology?**
   - A) MEDDPICC
   - B) SPIN
   - C) Challenger
   - D) Sandler
   - E) Value Selling
   - F) Custom/none

**If the user's request already provides most of this context, skip directly to the relevant step.** Lead with your best-effort answer using reasonable assumptions (stated explicitly), then ask only the most critical 1-2 clarifying questions at the end — don't gate your response behind gathering complete context.

## Step 2 — Coaching strategy

### Onboarding program design

**30-60-90 day framework:**

**Days 1-30 (Learn):**
- Company/product knowledge (what we sell, who we sell to, how we win)
- Sales process and methodology
- Tool training (CRM, sales engagement, enablement platform)
- Shadow 5+ calls with top performers
- Complete product certification
- **Milestone**: Pass product knowledge assessment (80%+ score)

**Days 31-60 (Practice):**
- Role-play discovery calls, demos, and objection handling
- Make first prospecting calls with manager listening
- Run first demo (manager shadows)
- Complete methodology certification (MEDDPICC, SPIN, etc.)
- **Milestone**: Successfully run a discovery call solo with positive manager feedback

**Days 61-90 (Perform):**
- Own pipeline independently
- Close first deal (or advance first opportunity past discovery)
- Receive weekly 1:1 coaching from manager
- Peer coaching sessions
- **Milestone**: Hit 50%+ of monthly quota

### Manager coaching framework

**Weekly 1:1 coaching structure (30 min):**
1. **Pipeline review** (10 min) — review top 3-5 deals, identify risks, plan next actions
2. **Skill coaching** (15 min) — review one call/meeting, identify one skill to improve, practice
3. **Goal setting** (5 min) — one specific action item for the week

**Coaching models:**
- **GROW**: Goal → Reality → Options → Will — structured coaching conversation
- **SBI**: Situation → Behavior → Impact — for giving feedback
- **Ask-Tell-Ask**: Ask what they think → Share your observation → Ask how they'll apply it

**Monthly coaching cadence:**
| Activity | Frequency | Duration | Purpose |
|---|---|---|---|
| 1:1 coaching | Weekly | 30 min | Pipeline + skill development |
| Call review | Weekly | 15 min | Review 1 recorded call together |
| Role-play | Bi-weekly | 20 min | Practice specific scenarios |
| Skill assessment | Monthly | 30 min | Evaluate progress on skill goals |
| Peer coaching | Monthly | 45 min | Small group practice and feedback |

### Role-play design

- **Structure**: Scenario brief (2 min) → Role-play (5-10 min) → Self-assessment (2 min) → Coach feedback (5 min)
- **Scenarios to cover**: Cold call, Discovery call, Demo, Objection handling (top 5 objections), Negotiation, Executive conversation
- **Scoring**: Use a rubric (1-5 scale) on specific skills: questioning, listening, positioning, handling objections, next steps
- **AI role-play**: Seismic's Role-Play Agent and similar AI tools can simulate buyer conversations for practice without needing a live partner

### Certification paths

- **Product certification**: Knowledge assessment on features, use cases, competitive positioning
- **Methodology certification**: Demonstrate methodology application in role-play scenarios
- **Skill-based certification**: Tiered badges (Bronze/Silver/Gold) for specific skills (discovery, negotiation, etc.)
- **Renewal**: Certifications expire annually — re-certify to ensure skills stay current

## Step 3 — Platform-specific guidance

For platform-specific coaching guidance (Seismic Learning, Allego, Gong/Chorus, MindTickle, SalesHood, Outdoo, Jiminny, Revenue.io, Enthu.AI, Demodesk, Balto, Cresta, Nooks, Orum, NICE CXone, Convin, MaestroQA, QEval, Solidroad, Playvox, SecondBody, Weflow, Winn.ai, Dialpad, Manual/Spreadsheet), see references/platforms.md.

## Step 4 — Measuring coaching impact

| Metric | What it measures | Target |
|---|---|---|
| Ramp time | Days from start to first quota attainment | Reduce by 20%+ |
| Time to first deal | Days from start to first closed-won | <90 days for new AEs |
| Quota attainment by cohort | % of quota hit by onboarding cohort | 70%+ by month 6 |
| Coaching session completion | % of scheduled 1:1s actually held | 90%+ |
| Certification pass rate | % passing on first attempt | 80%+ |
| Skill improvement score | Change in role-play/assessment scores over time | Positive trend |
| Rep retention | Turnover rate for coached vs uncoached reps | Lower for coached |

## Gotchas

- **Don't build an onboarding program without input from recent hires.** Claude tends to create theoretical programs. The best onboarding programs are designed with feedback from reps who completed onboarding in the last 6 months — they know what was missing.
- **Don't conflate coaching with training.** Training teaches knowledge (product, methodology). Coaching develops skills through practice and feedback. A rep who passed product training but can't run a discovery call needs coaching, not more training.
- **Don't skip the manager enablement.** Most coaching programs fail because managers aren't trained to coach. Build a "coaching the coaches" program before rolling out rep coaching at scale.
- **Don't make role-plays optional.** Reps avoid practice because it's uncomfortable. The best teams make role-play a required, scheduled activity — not a suggestion. Bi-weekly minimum.
- **Don't measure coaching by completion metrics alone.** 100% lesson completion doesn't mean reps are ready. Measure coaching impact by performance outcomes (ramp time, quota attainment, deal velocity) not just activity metrics.

- **Self-improving**: If you discover something not covered here, append it to `references/learnings.md` with today's date.

## Before recommending a specific platform skill

This skill covers a strategy domain across many platforms. **Before pointing the user to any specific platform skill** (any `/sales-{platform}` listed in `## Related skills`, e.g., `/sales-mailshake`, `/sales-klaviyo`, `/sales-apollo`), read that platform skill's actual `SKILL.md` first. The 1-line description in `## Related skills` is enough to *identify* a candidate — it's not enough to *commit* to it or to write a prompt that invokes it well.

**How to read it:**
- If `~/.claude/skills/{skill-name}/SKILL.md` exists locally, `Read` it.
- For `sales-*` skills, `WebFetch` directly from this repo: `https://raw.githubusercontent.com/sales-skills/sales/main/skills/{skill-name}/SKILL.md` — e.g., for `sales-mailshake`: `https://raw.githubusercontent.com/sales-skills/sales/main/skills/sales-mailshake/SKILL.md`.
- For non-`sales-*` skills (third-party), look up `{org}/{repo}` in `~/.claude/skills/sales-do/references/skill-sources.md` if installed and fetch the same `skills/{s