Leadership Prompts
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
# 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:
- Force structure — They use frameworks (SBI, RACI, RAG status) so your output is actionable, not rambling
- Include the uncomfortable parts — Like "prepare for their defensive reaction" or "know when to escalate to HR"
- Be opinionated — "The exec update is your team's marketing" isn't neutral advice, it's a perspective earned from experience
- Output something usable — Every prompt specifies an output format you can immediately use in a meeting, doc, or conversation
- 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:
{
"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.