Build a Coaching Plan

Sales Leader, Enablement.

• Monthly one-on-ones that have become status updates.
• When a rep is missing number and the cause is unclear.

• The rep's recent numbers: activity, conversion by stage
• Two or three call or deal observations
• What the rep thinks they need to work on

Best for one task. Copy it, add your information, and run it in your AI assistant.

You are a sales coach. Here is one rep's data: [paste numbers and observations]. The rep says they want to improve: [paste]. Build a 30-day coaching plan: the single skill to focus on and the evidence for choosing it, two weekly practice activities, what I should observe on calls, and how we will both know at day 30 whether it worked. One skill only. If the data points at a different skill than the rep's self-assessment, say so and explain.

Best for repeatable work. The file includes the process, required inputs, decision rules, quality checks, and output format.

---
name: build-sales-coaching-plan
description: A 30-day coaching plan for one rep: the one skill to build, the evidence, and how you will both know it worked.
license: MIT
metadata:
  author: The Revenue AI Report
  version: 1.0.0
  last-reviewed: 2026-09-04
  source: https://www.therevenueaireport.com/skills/build-sales-coaching-plan
---

# Build a Coaching Plan

A 30-day coaching plan for one rep: the one skill to build, the evidence, and how you will both know it worked.

## When to use this skill

- Monthly one-on-ones that have become status updates.
- When a rep is missing number and the cause is unclear.

## Inputs to collect

- The rep's recent numbers: activity, conversion by stage
- Two or three call or deal observations
- What the rep thinks they need to work on

## Process

1. Gather numbers and real observations, not impressions.
2. Ask the rep what they think first. Put it in the input.
3. Generate the plan. One skill. Cut everything else.
4. Agree on the day-30 measure together so the verdict is shared.
5. Review weekly for ten minutes. Adjust the practice, not the target.

## Decision rules

- One skill per 30 days. Two skills means no focus.
- If the data and the rep disagree, coach the data but show the rep why.
- No movement at day 30 means the diagnosis was wrong. Re-diagnose; do not extend the same plan.

## Output requirements

- One skill, chosen with evidence.
- Two weekly practice activities and call-observation points.
- The day-30 success measure.

## Quality checks

- The skill choice cites the rep's own numbers.
- The success measure is observable, not a vibe.
- The rep agreed to the measure.

## Limitations

- The plan is only as good as the observations. Secondhand impressions produce generic plans.
- Coaching fails without the manager's follow-through. The AI cannot run the one-on-ones.

## Example input

Rep converts stage 1 to 2 at team rate but stage 2 to 3 at half the team rate. Observed calls: strong discovery, then sends a proposal before confirming the buying process.

## Example output

Focus skill: confirming the buying process before proposing. Evidence: deals die after the proposal, not before it. Practice: on every stage-2 call this month, the rep asks how the last similar purchase was approved and names the answer in the CRM. Day-30 measure: stage-2-to-3 conversion within 20 percent of team rate.

## Review checklist

- One skill only?
- Rep agreed to the measure?
- Weekly review on the calendar?

## Works with

- Playbook: Make conversation data do work (L3) (sales, L3) https://www.therevenueaireport.com/playbooks/conversation-data-to-work-l3
- Playbook: ChatGPT for first-draft cold emails (L1) (sales, L1) https://www.therevenueaireport.com/playbooks/chatgpt-cold-email-drafts-l1
- Playbook: Score your ICP on stack density (L4) (revops, L4) https://www.therevenueaireport.com/playbooks/score-icp-on-stack-density-l4
- Tool: Mindtickle Call AI (Sales & Revenue Intelligence) https://www.therevenueaireport.com/tools/mindtickle-call-ai
- Tool: Jiminny (Meeting & Voice AI) https://www.therevenueaireport.com/tools/jiminny
- Tool: Balto (Sales & Revenue Intelligence) https://www.therevenueaireport.com/tools/balto
- Tool: Cu (Meeting & Voice AI) https://www.therevenueaireport.com/tools/cu
- Tool: ExecVision (Sales & Revenue Intelligence) https://www.therevenueaireport.com/tools/execvision

## Rules of conduct

- Write for a Director, VP, or operator. Short sentences. Explain uncommon terms.
- Separate facts from assumptions. Never hide uncertainty.
- Do not invent numbers, benchmarks, quotes, or customer names.
- Do not send messages, change CRM records, or publish anything unless the user explicitly asks.
- Flag when a decision needs human review.

## Evidence

This skill is grounded in The Revenue AI Report research:
- https://www.therevenueaireport.com/research/what-works
- Related analysis: https://www.therevenueaireport.com/blog/single-player-ai-problem




Source and updates: https://www.therevenueaireport.com/skills/build-sales-coaching-plan

1. 1.Gather numbers and real observations, not impressions.
2. 2.Ask the rep what they think first. Put it in the input.
3. 3.Generate the plan. One skill. Cut everything else.
4. 4.Agree on the day-30 measure together so the verdict is shared.
5. 5.Review weekly for ten minutes. Adjust the practice, not the target.

• One skill per 30 days. Two skills means no focus.
• If the data and the rep disagree, coach the data but show the rep why.
• No movement at day 30 means the diagnosis was wrong. Re-diagnose; do not extend the same plan.

• One skill, chosen with evidence.
• Two weekly practice activities and call-observation points.
• The day-30 success measure.

Rep converts stage 1 to 2 at team rate but stage 2 to 3 at half the team rate. Observed calls: strong discovery, then sends a proposal before confirming the buying process.

Focus skill: confirming the buying process before proposing. Evidence: deals die after the proposal, not before it. Practice: on every stage-2 call this month, the rep asks how the last similar purchase was approved and names the answer in the CRM. Day-30 measure: stage-2-to-3 conversion within 20 percent of team rate.

• One skill only?
• Rep agreed to the measure?
• Weekly review on the calendar?

What does the Build a Coaching Plan skill do?

A 30-day coaching plan for one rep: the one skill to build, the evidence, and how you will both know it worked.

Who is the Build a Coaching Plan skill for?

Sales Leader, Enablement. It sits at the start here level and takes about 20 minutes per rep.

What do I need before I start?

Collect these first: The rep's recent numbers: activity, conversion by stage; Two or three call or deal observations; What the rep thinks they need to work on.

What is the difference between the quick prompt and the SKILL.md file?

The quick prompt is for one task. Copy it, add your information, run it. The SKILL.md file is for repeatable work: it carries the process, required inputs, decision rules, quality checks, and output format so an AI assistant runs the same way every time.

What should I check before trusting the output?

One skill only? Rep agreed to the measure? Weekly review on the calendar?

Is it free to use?

Yes. Every skill on The Revenue AI Report is free and published under the MIT license. Attribution is welcome, not required.

• The plan is only as good as the observations. Secondhand impressions produce generic plans.
• Coaching fails without the manager's follow-through. The AI cannot run the one-on-ones.

Run the skill, then roll it out with a playbook. Vendor links are supporting context, not a recommendation.

• Playbook: Make conversation data do work (L3) (sales, L3 L3 Integrated)
• Playbook: ChatGPT for first-draft cold emails (L1) (sales, L1 L1 Starter)
• Playbook: Score your ICP on stack density (L4) (revops, L4 L4 Orchestrated)
• Tool: Mindtickle Call AI (Sales & Revenue Intelligence)
• Tool: Jiminny (Meeting & Voice AI)
• Tool: Balto (Sales & Revenue Intelligence)
• Tool: Cu (Meeting & Voice AI)
• Tool: ExecVision (Sales & Revenue Intelligence)

• Research: what works
• Related analysis