How to Have a Skip-Level 1-on-1 with a Director or VP (For ICs) | A Proven AI Prompt for leadership for engineers | Engify.ai
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# How to Have a Skip-Level 1-on-1 with a Director or VP (For ICs)

You are an individual contributor preparing for a skip-level 1-on-1 with your Director or VP (your manager's manager). This is your opportunity to share feedback, discuss career growth, and build relationship with senior leadership.

## Context
- **Your Role**: [Engineer / Product Manager / Designer / etc.]
- **Your Level**: [Junior / Mid / Senior / Staff / Principal]
- **Director/VP**: [Name, Title]
- **Your Manager**: [Manager Name]
- **How You Got This Meeting**: [They scheduled it / You requested it / Regular cadence]
- **Purpose**: [Career discussion / Feedback session / Regular check-in / Specific concern]

## Pre-Meeting Preparation

### Understand Why Skip-Levels Exist
- Directors/VPs want to stay connected to the organization
- They want honest feedback about what's working and what's not
- They want to identify and develop future leaders
- They want to catch issues early before they become problems

### Know What's Appropriate
**Good Topics:**
- Career development and growth
- Feedback about organization, culture, processes
- Ideas for improvement
- Your experience working here
- Concerns about team or organization (not personal drama)
- Questions about strategy or direction

**Not Appropriate:**
- Complaining solely about your manager (unless serious issue)
- Personal disputes with colleagues
- Gossip or rumors
- Criticizing individuals unfairly
- Asking for raises or promotions directly

### Prepare Your Talking Points

**1. Career Development**
- [ ] What skills do you want to develop?
- [ ] What roles or opportunities interest you?
- [ ] What would help you grow?
- [ ] What's your career trajectory?

**2. Feedback About Organization**
- [ ] What's working well?
- [ ] What would you change?
- [ ] Process improvements?
- [ ] Culture observations?

**3. Your Experience**
- [ ] What's energizing you?
- [ ] What's challenging?
- [ ] What support do you need?
- [ ] Are you getting what you need?

**4. Ideas & Suggestions**
- [ ] Process improvements
- [ ] Tool or workflow ideas
- [ ] Team structure suggestions
- [ ] Strategic ideas

**5. Questions**
- [ ] Questions about strategy
- [ ] Questions about organization
- [ ] Questions about career paths
- [ ] Questions about growth opportunities

## During the Meeting

### Opening (Let Them Lead)

**They'll Usually:**
- Thank you for meeting
- Set tone (safe space, honest feedback)
- Ask how you're doing

**Your Response:**
- Be authentic and honest
- Thank them for the opportunity
- Share how you're doing overall

### Share Your Topics

**Be Specific:**
- Use concrete examples
- Avoid vague complaints
- Focus on solutions, not just problems
- Be constructive, not just critical

**Example - Good:**
"I've noticed our code review process is slow. When we have 5+ reviewers on every PR, it takes 3-4 days to merge. I think we could streamline by having primary reviewers and optional reviewers. This would help us ship faster."

**Example - Not Good:**
"Our code review process sucks. It's too slow and I hate it."

### Career Discussion

**If They Ask About Career:**
- Share your goals authentically
- Be specific about what you want
- Ask for their advice
- Express interest in opportunities

**Example:**
"I'm interested in moving toward a Staff Engineer role. I've been working on [specific skills], and I'd love to get more opportunities to [lead initiatives / mentor others / architectural work]. What advice do you have for getting there?"

### Feedback About Manager

**Be Constructive:**
- Focus on behaviors, not personality
- Share what would help you
- Be fair and balanced
- Don't just complain

**If Manager is Great:**
- Share positive feedback
- "I really appreciate [specific thing]"
- "They've helped me grow by [example]"

**If Manager Has Issues:**
- Be specific and constructive
- "I'd love more feedback on [specific area]"
- "It would help if [specific behavior change]"
- Avoid personal attacks

**If You Have Serious Concerns:**
- Share factual concerns
- Focus on impact
- Express what you need
- Be open to solutions

### Organizational Feedback

**Share Observations:**
- What's working well (celebrate wins)
- What could be improved (constructive suggestions)
- Process friction you're experiencing
- Culture observations

**Be Balanced:**
- Don't just complain
- Share positive feedback too
- Offer solutions when possible
- Focus on improvement

### Ask Questions

**Strategic Questions:**
- "What's the strategy for [area]?"
- "How do you see [initiative] evolving?"
- "What are the biggest challenges facing [organization]?"

**Career Questions:**
- "What does success look like at [next level]?"
- "What opportunities are coming up?"
- "How do you see [career path]?"

**Growth Questions:**
- "What should I focus on to grow?"
- "Who should I learn from?"
- "What experiences would help me develop?"

### Closing

**If They Ask "Anything Else?":**
- Share anything important you haven't mentioned
- Ask for follow-up if needed
- Express appreciation

**End Professionally:**
- "Thanks for your time and insights"
- "I appreciate the opportunity to share feedback"
- "I'm excited about [something discussed]"

## Post-Meeting

### Follow-Up Actions
- [ ] Complete any action items you committed to
- [ ] Send thank you email (brief)
- [ ] Share relevant updates with your manager (don't triangulate)
- [ ] Follow up on opportunities discussed

### Thank You Email Template

**Subject**: Thank you - Skip-Level 1-on-1

Hi [Director/VP Name],

Thanks for taking time to meet with me today. I really appreciated:

- [Specific thing they shared]
- [Specific insight or feedback]
- [Specific opportunity discussed]

I'm excited about [something discussed] and will follow up on [action item].

Thanks again,
[Your Name]

### Maintain Relationship
- Don't just disappear after the meeting
- Follow up periodically if appropriate
- Share updates on discussed topics
- Don't over-communicate (respect their time)

## Common Mistakes to Avoid

### ❌ Don't:
- **Complain about your manager unfairly** - Be constructive
- **Gossip or share rumors** - Stay factual
- **Ask for raise/promotion directly** - Focus on growth first
- **Be overly negative** - Balance feedback with positives
- **Overstay your welcome** - Respect time limits
- **Ignore your manager** - Keep them in the loop appropriately

### ✅ Do:
- **Be honest and authentic** - Share real feedback
- **Be constructive** - Offer solutions, not just problems
- **Focus on growth** - Show you're invested in your development
- **Be prepared** - Come with specific topics and questions
- **Follow through** - Complete action items
- **Respect boundaries** - Understand their role and time

## When to Request a Skip-Level

**Request One If:**
- You have organizational feedback to share
- You want career guidance
- You've tried resolving issues with manager
- You have strategic questions
- You want to build relationship with leadership

**Don't Request Just To:**
- Bypass your manager unnecessarily
- Complain about minor issues
- Show off or network excessively
- Avoid conflict with manager

## Sample Closing Statement

"I'm really grateful for this opportunity. I value the direct connection with leadership and I'm excited about [your growth / the organization's direction / discussed opportunities]. I'll follow up on [action items] and look forward to continuing to contribute to [organization/team]."

## Remember
- Skip-levels are a privilege, not a right
- Use them wisely and constructively
- Build trust through honest, thoughtful feedback
- Follow through on commitments
- Respect your manager's role
How to Have a Skip-Level 1-on-1 with a Director or VP (For ICs)

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