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:
- 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
- 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)
- 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
- 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):
- Pipeline review (10 min) — review top 3-5 deals, identify risks, plan next actions
- Skill coaching (15 min) — review one call/meeting, identify one skill to improve, practice
- 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.mdwith 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.mdexists locally,Readit. - For
sales-*skills,WebFetchdirectly from this repo:https://raw.githubusercontent.com/sales-skills/sales/main/skills/{skill-name}/SKILL.md— e.g., forsales-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.mdif installed and fetch the sameskills/{skill-name}/SKILL.mdpath under that repo.
After reading, ground your recommendation in something concrete from the SKILL.md (its scope, a sub-flow, its argument-hint shape, or a "Do NOT use for..." negative trigger). Align any generated invocation with the platform skill's argument-hint. If the platform skill turns out not to fit the user's situation, swap to another or handle the question here directly rather than recommending a poor fit.
Related skills
/sales-seismic— Seismic platform help (for Seismic Learning, Role-Play Agent, and coaching features)/sales-allego— Allego platform help (for Modern Learning, AI Role-Play, and Conversation Intelligence)/sales-gong— Gong platform help (coaching scorecards, deal boards, Smart Trackers, conversation analytics)/sales-rilla— Rilla platform help (field sales AI coaching, virtual ridealongs, home services focus)/sales-siro— Siro platform help (field sales AI coaching, Halftime real-time coaching, multi-industry)/sales-salesask— Sales Ask platform help (field + call center AI coaching, Coach Dean active feedback, home services vertical)/sales-craft— Craft platform help (real-time in-appointment AI coaching, 24/7 AI call center, revenue recovery agents, home services)/sales-outdoo— Outdoo platform help (AI roleplay coaching, conversation intelligence, revenue intelligence, CRM automation, mid-market Gong alternative)/sales-jiminny— Jiminny platform help (coaching-focused conversation intelligence, revenue intelligence, 8 CRM integrations, mid-market Gong alternative)/sales-enthu— Enthu.AI platform help (contact center QA with auto-scoring, agent coaching, compliance monitoring, affordable Gong alternative)/sales-demodesk— Demodesk platform help (AI coaching scorecards, conversation intelligence, autonomous AI agents, GDPR-native)/sales-clari-copilot— Clari Copilot platform help (real-time battlecards, live coaching during calls, coaching scorecards, gametapes, enterprise CI)/sales-revenue-io— Revenue.io platform help (Salesforce-native, Moments real-time in-call coaching, AI scoring with 400+ criteria, Revenue Intelligence dashboards)/sales-salesken— Salesken platform help (AI conversation intelligence, real-time in-call coaching, QA automation on 100% of calls, multilingual transcription, APAC focus)/sales-balto— Balto platform help (real-time AI coaching for contact centers, automated QA, compliance monitoring)/sales-cresta— Cresta platform help (enterprise contact center AI — real-time agent assist, AI virtual agents, conversation intelligence, automated QA)/sales-convin— Convin platform help (contact center AI with 100% automated QA, Real-Time Assist, AI Phone Call agent, LMS, 70+ languages)/sales-maestroqa— MaestroQA platform help (conversation data QA with customizable scorecards, coaching workflows, AskAI analytics, 60+ integrations)/sales-playvox— Playvox platform help (modular WEM with QA scorecards, WFM, coaching/eLearning, gamification, now part of NICE)/sales-qeval— QEval platform help (AI-powered contact center QA with 100% automated scoring, compliance monitoring, agent coaching, $40-100/user/mo)/sales-solidroad— Solidroad platform help (AI QA + training closed-loop, 100% automated scoring, AI practice simulations from quality gaps, $10-50/user/mo)/sales-secondbody— SecondBody platform help (voice-first AI roleplay, Rory AI coach, methodology scoring SPIN/MEDDIC/Sandler, unlimited seats at $30/user/mo Pro, daily practice habit model)/sales-uniphore— Uniphore platform help (enterprise conversation intelligence, U-Assist real-time coaching, automated QA, CSATai, Emotion AI)/sales-nooks— Nooks platform help (AI parallel dialer with built-in call scoring, roleplay, battlecards, virtual salesfloor)/sales-orum— Orum platform help (AI parallel dialer with AI Coaching Suite, scorecards, roleplay, virtual salesfloor)/sales-momentum— Momentum platform help — AI revenue orchestration with Coaching Agent for data-driven call scoring, churn signals, and executive briefs (acquired by Salesforce Feb 2026)/sales-nice-cxone— NICE CXone platform help (built-in QM coaching, AI Copilot, Interaction Analytics, $135-209/agent/mo for coaching-relevant tiers)/sales-genesys— Genesys Cloud CX platform help (built-in QM coaching, AI agent assist on CX 4, Interaction Analytics, $75-240/user/mo)/sales-ccaas-selection— Comparing CCaaS platforms? The selection skill walks through Genesys vs NICE vs Talkdesk vs Five9/sales-modjo— Modjo platform help (EU-native call scoring, AI coaching insights, conversation library playlists, GDPR-compliant)/sales-winn— Winn.ai platform help (real-time playbook adherence tracking, automated CRM updates, live coaching Enterprise, AI battle cards)/sales-rafiki— Rafiki platform help (AI conversation intelligence with Smart Call Scoring MEDDIC/BANT/SPIN, Role Play Agent, CRM auto-sync, $19-49/user/mo)/sales-call-review— Review specific sales calls and extract coaching insights/sales-note-taker— Picking an AI note-taker (Fathom, Fireflies, Avoma, Gong, Modjo, etc.) or wiring its API to feed your coaching program/sales-content— Sales content for training and enablement programs/sales-do— Not sure which skill to use? The router matches any sales objective to the right skill. Install:npx skills add sales-skills/sales --skill sales-do
Examples
Example 1: 90-day onboarding program
User says: "Build a 90-day onboarding program for new AEs" Skill does:
- Creates a 30-60-90 framework with specific milestones per phase
- Designs assessment gates at each phase transition (knowledge test, role-play pass, quota milestone)
- Includes shadowing schedule, role-play exercises, and certification path
- Defines measurable ramp metrics (time to first deal, quota attainment by month 6)
- Recommends tools and tracking approach based on team size Result: Full onboarding program with milestones, assessments, and a ramp measurement plan
Example 2: Manager coaching framework
User says: "Create a coaching framework for our 8 frontline sales managers" Skill does:
- Designs a weekly 1:1 coaching structure (pipeline review + skill coaching + goal setting)
- Introduces the GROW coaching model for structured coaching conversations
- Builds a monthly coaching cadence (1:1s, call reviews, role-plays, peer coaching)
- Includes a "coaching the coaches" enablement plan for managers who have never coached
- Creates a coaching scorecard to track manager coaching effectiveness Result: Complete coaching framework with cadence, models, and manager enablement plan
Example 3: Seismic Learning role-plays
User says: "We're using Seismic Learning — how do I set up role-plays for objection handling?" Skill does:
- Walks through creating practice exercises with specific objection scenarios
- Designs a scoring rubric for video/text submissions (1-5 on acknowledge, clarify, respond, check)
- Explains how to use Seismic's AI Role-Play Agent for automated buyer simulation
- Recommends tracking completion rates and correlating with call performance in Gong/Chorus
- Sets up a bi-weekly role-play cadence with manager review Result: Seismic Learning role-play setup guide with scenarios, scoring rubric, and AI practice configuration
Troubleshooting
New reps ramp too slowly
Cause: Onboarding is too knowledge-heavy and not enough practice Solution: Add more role-plays, shadowing, and real-world exercises in weeks 2-4. Shift from 80/20 training-to-practice to 50/50 by day 15. Have new reps make their first prospecting calls by week 2 with a manager listening, not week 6.
Managers skip coaching sessions
Cause: No accountability and no structure Solution: Provide coaching templates so managers don't have to build the agenda from scratch. Make 1:1 completion a manager KPI reported to leadership. Train managers on the coaching framework — most skip sessions because they don't know what to do in them.
Reps pass training but underperform
Cause: Assessment measures knowledge recall, not skill application Solution: Add practical assessments (recorded role-plays scored on a rubric) alongside knowledge tests. A rep who can recite MEDDPICC but can't run a discovery call needs practice, not another quiz. Require role-play pass before certifying reps as "ramped."