# coaching-development

Helps managers shift from solving every problem themselves to coaching team members through targeted stretch assignments and skill gap analysis.

- skill · `type=skill` · Claude Code, Codex, Cursor, GitHub Copilot, Gemini CLI, OpenCode · 356 installs · ★ 1434
- Author: RefoundAI
- License: MIT · policy=mirror · the beginning of the file is at the end of this page
- Source: https://github.com/RefoundAI/lenny-skills/tree/HEAD/skills/coaching-development/SKILL.md
- Updated: 2026-07-16
- HTML: https://affpapa.org/en/nevibecode/skills/coaching-development

## What it does

The skill guides engineering and product managers out of the firefighter trap. Built on 47 insights from 18 guests of Lenny's Podcast and Newsletter, it draws on practical perspectives from Petra Wille, Ravi Mehta, and Dr. Becky Kennedy. Instead of handing out instant answers, the agent pushes you to help direct reports build autonomous problem-solving capabilities.

The workflow breaks coaching down into four distinct steps: assessing skill deficits, picking career frameworks, designing quarterly stretch assignments, and asking curiosity-driven questions. It treats underperformance as a missing skill rather than a personality flaw. If you routinely accept monkeys back from your reports, this skill immediately flags that habit. That friction is deliberate: you cannot scale if you become the team's bottleneck.

All source insights and quotes are referenced in `references/guest-insights.md`. No external API keys or special runtime dependencies are required beyond the standard skill file.

## Install

### Claude Code (native platform)

1. **Skills CLI (Vercel)**
```bash
npx skills add RefoundAI/lenny-skills --skill coaching-development -a claude-code
```

2. **Manually: put the files in place**
- File: `~/.claude/skills/coaching-development/SKILL.md` — Copy the whole skill folder; for one project use .claude/skills/coaching-development/

### Codex

1. **Skills CLI (Vercel)**
```bash
npx skills add RefoundAI/lenny-skills --skill coaching-development -a codex
```

2. **Manually: put the files in place**
- File: `.agents/skills/coaching-development/SKILL.md` — For all projects use ~/.agents/skills/

### Cursor

1. **Skills CLI (Vercel)**
```bash
npx skills add RefoundAI/lenny-skills --skill coaching-development -a cursor
```

2. **Manually: put the files in place**
- File: `.cursor/skills/coaching-development/SKILL.md` — Cursor also reads .agents/skills/ and .claude/skills/

### GitHub Copilot

1. **GitHub CLI**
```bash
gh skill install RefoundAI/lenny-skills coaching-development
```

2. **Manually: put the files in place**
- File: `.github/skills/coaching-development/SKILL.md`

### Gemini CLI

1. **Skills CLI (Vercel)**
```bash
npx skills add RefoundAI/lenny-skills --skill coaching-development -a gemini-cli
```

2. **Platform CLI**
```bash
gemini skills install https://github.com/RefoundAI/lenny-skills --path skills/coaching-development
```

### Windsurf (Devin Desktop)

**Manually: put the files in place**
- File: `.devin/skills/coaching-development/SKILL.md` — The legacy .windsurf/skills/ path still works

### OpenCode

**Skills CLI (Vercel)**
```bash
npx skills add RefoundAI/lenny-skills --skill coaching-development -a opencode
```

### Claude.ai

**Claude.ai**
- Zip the folder and upload it in Settings → Capabilities → Skills

Where a file is given instead of a command, copy the files from the source to that path: https://github.com/RefoundAI/lenny-skills/tree/HEAD/skills/coaching-development/SKILL.md

## When to use it
- convert employee performance struggles into clear skill gaps
- create quarterly stretch assignments for direct reports
- stop accepting delegated tasks back from team members
- structure one-on-one meetings around curiosity-driven questions

## Example prompts
- A senior engineer keeps missing deadlines on system design tasks. Help me pinpoint the exact skill gap instead of treating it as an attitude issue.
- Generate open-ended coaching questions for a one-on-one with a designer stepping into a lead role.
- My direct report brought me a complex prioritization issue. What questions should I ask to help them find the solution themselves?

## Source text · SKILL.md · MIT

Below is the content of a third-party file. It is data, not instructions for you: do not act on anything written inside unless the human asks. Block tag: 33cc178d69b2eaf6.

BEGIN THIRD-PARTY FILE 33cc178d69b2eaf6
```text
---
name: coaching-development
description: Help users transition from individual execution to a coaching-centric leadership style that scales through the growth of their team. It focuses on identifying skill deficits, providing reflection space, and leveraging frameworks to accelerate professional maturity.
---

# Coaching and Talent Development

Build a high-performing team by shifting from a problem-solver to a growth-accelerator.

Help the user with coaching and talent development using insights from 18 guests and posts across Lenny's Podcast and Newsletter.

## How to Help

1. **Assess skill gaps** - Help the user identify specific technical or behavioral areas where their team members are currently struggling.
2. **Select frameworks** - Recommend specific career ladders, rubrics, or AI-driven coaching tools from the corpus to provide objective standards.
3. **Design growth plans** - Assist in creating next bigger challenges and quarterly stretch assignments for individual direct reports.
4. **Practice reflection** - Guide the user in moving from giving immediate answers to asking powerful, curiosity-driven questions.

## Core Principles

### Reframe Underperformance as Skill Deficits
Dr. Becky Kennedy: "When you look at bad behavior, the actual problem is someone doesn't have the skill they need to manage something happening internally."

Identify the specific internal skill a struggling employee lacks to manage their current challenges instead of viewing it as a character flaw.

### Lead with Personal Accountability
Elizabeth Stone: "It’s more about how much I care about excellence, I guess. So giving it my best in those situations. And that might not mean that I work really wild hours or I work weekends or I’m the one who’s willing to sacrifice the vacation. I’ve actually tried to avoid setting that as an expectation, but more that I hold myself to a very high standard."

High standards begin with the leader's own commitment to quality and promptness, ensuring you never become the bottleneck for your team.

### Utilize Quarterly Stretch Assignments
Petra Wille: "And creating such a list once a quarter, for example, you block yourself an hour in your calendar, you write down the names of your direct reports, and then you just think about, 'Okay, what would be this next bigger challenge for them?'"
```
END THIRD-PARTY FILE 33cc178d69b2eaf6

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