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, MindTickle, SalesHood, Brainshark), conversation intelligence tool (Gong, Chorus), or manual approach.
Step 1 — Gather context
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) Gong/Chorus (conversation intelligence)
- C) MindTickle
- D) Brainshark
- E) SalesHood
- F) LMS (generic)
- G) Spreadsheets/manual
- H) 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
In Seismic Learning (formerly Lessonly)
- Lessons: Create interactive lessons with text, video, images, and practice exercises. Assign to individuals or teams with due dates.
- Practice exercises: Built-in role-play with video/text submission. Manager reviews and scores responses.
- Learning Paths: Chain lessons into structured programs (onboarding, certification, skill tracks).
- AI Role-Play Agent: Generative AI simulates buyer conversations based on your content in Seismic. Provides instant feedback.
- Reporting: Track completion rates, assessment scores, and time-to-completion. Correlate with sales performance.
- Integration: Syncs with Salesforce for tying learning completion to rep performance metrics.
In Gong / Chorus
- Call coaching: Review recorded calls with AI-generated insights (talk ratio, questions asked, topics discussed).
- Scorecards: Rate calls against methodology criteria. Track improvement over time.
- Deal boards: Coach on deal execution by reviewing conversation patterns across the deal cycle.
- Limitations: Great for call coaching but doesn't cover onboarding, certifications, or structured learning paths.
In MindTickle
- Sales readiness: Combines content, training, and coaching in one platform.
- Role-play: AI-powered practice with scoring and feedback.
- Ideal Rep Profile: Benchmark skills against top performers.
- Analytics: Readiness index scores across the team.
In SalesHood
- Video coaching: Reps record practice pitches for manager review.
- Huddles: Team coaching sessions with structured agendas.
- Playbooks: Step-by-step guides with embedded learning.
Manual / Spreadsheet approach
- Google Docs: Create onboarding checklists and coaching templates. Works for <10 reps.
- Spreadsheet tracker: Track certification completion, role-play scores, coaching session notes.
- Limitations: No engagement tracking, no automated assignments, no AI practice. Breaks down fast above 10 reps.
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.
Related skills
- — Seismic platform help (for Seismic Learning, Role-Play Agent, and coaching features)
- — Review specific sales calls and extract coaching insights
- — Sales content for training and enablement programs
- — Not sure which skill to use? The router matches any sales objective to the right skill. Install:
npx skills add sales-skills/sales --skills 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."