Leadership Prompts

Curated collection of 25+ battle-tested prompts for engineering leaders — 1-on-1 prep, team health, incident retros, technical strategy, hiring, career development, and stakeholder communication. Built from 13+ years of engineering management experience.

Battle-tested prompt library for engineering managers, tech leads, VPs of Engineering, and CTOs. These aren't generic "tell me about leadership" prompts — they're specific, opinionated frameworks for real challenges you face weekly.

Who This Is For

• Engineering Managers running teams of 5-15
• Tech Leads navigating the IC-to-management boundary
• Directors/VPs managing managers
• CTOs who still get their hands dirty

Categories

Category	Count	When to reach for it
1-on-1 Prep	4	Before any non-routine 1-on-1
Team Health	4	After rough quarters, conflicts, layoffs, or remote disconnection
Incident Retrospectives	3	Within 48h of incident resolution
Technical Strategy	4	Quarterly planning, architecture reviews, build-vs-buy decisions
Hiring & Interviews	3	Opening new roles, optimizing pipeline, closing candidates
Career Development	4	Promotion cycles, feedback delivery, retention conversations
Stakeholder Communication	4	Exec updates, saying no, cross-functional alignment, reorgs

Quick Start

Using the CLI

bash

# List all categories
node scripts/leadership-prompts.js list

# Get a random prompt (great for manager skill-building)
node scripts/leadership-prompts.js random

# Search by keyword
node scripts/leadership-prompts.js search "promotion"

# Show a specific prompt by ID
node scripts/leadership-prompts.js show career-dev-promotion

# Get all prompts in a category
node scripts/leadership-prompts.js category "Team Health"

Using with Your AI Assistant

Just tell your assistant:

"I need to prepare for a 1-on-1 with an underperformer. Use the leadership-prompts skill to find the right prompt, then walk me through it."

Or for browsing:

"Show me all the hiring prompts from leadership-prompts"

How to Use a Prompt

Each prompt has placeholder variables in {curly_braces}. Fill these in with your specific context. The more specific you are, the better the output.

Example:

The prompt says:

I'm preparing for a 1-on-1 with a direct report who has been underperforming for the past {timeframe}...

You fill in:

I'm preparing for a 1-on-1 with a direct report who has been underperforming for the past 6 weeks...

Prompt Design Principles

These prompts are designed to:

1. Force structure — They use frameworks (SBI, RACI, RAG status) so your output is actionable, not rambling
2. Include the uncomfortable parts — Like "prepare for their defensive reaction" or "know when to escalate to HR"
3. Be opinionated — "The exec update is your team's marketing" isn't neutral advice, it's a perspective earned from experience
4. Output something usable — Every prompt specifies an output format you can immediately use in a meeting, doc, or conversation
5. Acknowledge politics — Real leadership happens in political contexts. These prompts include stakeholder dynamics, not just best practices

Adding Your Own Prompts

Add entries to prompts.json following the existing schema:

json

{
  "id": "category-short-name",
  "category": "Category Name",
  "title": "Human-readable title",
  "prompt": "The actual prompt text with {variables}",
  "context": "When to use this prompt",
  "output_format": "What the AI should produce",
  "example": "A filled-in example showing real usage"
}

Credits

Created by Rob — engineering manager since 2011, currently running leadingin.tech. These prompts come from real situations managing teams at startups and scale-ups, not from management textbooks.