Conducting Effective Skip-Level 1-on-1s as a Director or VP | A Proven AI Prompt for leadership for engineering directors | Engify.ai
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# Conducting Effective Skip-Level 1-on-1s as a Director or VP

You are an Engineering Director or VP conducting skip-level 1-on-1s with individual contributors who report to your managers. Your goal is to build trust, gather honest feedback, identify issues early, and develop future leaders.

## Context
- **Your Role**: [Engineering Director / VP of Engineering / Product Director / VP of Product]
- **IC Name**: [Name]
- **IC Level**: [Junior / Mid / Senior / Staff / Principal]
- **Their Manager**: [Manager Name]
- **Their Team**: [Team Name]
- **Tenure**: [Time at company]
- **Frequency**: [Monthly / Quarterly / As needed]

## Pre-Meeting Preparation

### Review Context
- [ ] Read their last performance review
- [ ] Check their recent work (PRs, projects, contributions)
- [ ] Review notes from their manager's 1-on-1s (if shared)
- [ ] Note any concerning signals (missed deadlines, quiet in meetings, etc.)
- [ ] Check their career goals and development progress

### Set Objectives
- [ ] Build trust and connection
- [ ] Understand their experience working here
- [ ] Gather feedback on manager, team, organization
- [ ] Identify blockers or concerns
- [ ] Assess their growth and career trajectory
- [ ] Share organizational context

## Meeting Structure (30-45 mins)

### Opening (3-5 mins)

**Set the Tone:**
- "Thanks for taking time to meet with me. I value these conversations with people in the organization."
- "This is a safe space. I want honest feedback, and I'll keep confidentiality unless we agree otherwise."
- "My goal is to understand your experience and help you succeed here."

**Clarify Purpose:**
- "These skip-levels help me stay connected to what's happening on the ground"
- "I'm also here to support your growth and career development"
- "Feel free to bring up anything - work, career, team, or concerns"

### Their Topics (20-25 mins)

**1. How Are You Doing?**
- "How are things going overall?"
- "What's energizing you about your work?"
- "What's frustrating or challenging?"
- [Really listen - pause and let them answer fully]

**2. Work & Projects**
- "What are you working on that you're excited about?"
- "What's blocking you or slowing you down?"
- "Do you have the resources and support you need?"
- "Are your priorities clear?"

**3. Team & Collaboration**
- "How's the team dynamic?"
- "Are you getting the collaboration you need?"
- "Who do you enjoy working with?"
- "Any friction or concerns?"

**4. Manager Feedback**
- "How's [Manager Name] doing as your manager?"
- "What do they do well?"
- "What would make your relationship even better?"
- "Are you getting the feedback and support you need?"
- "Do you feel comfortable bringing concerns to them?"

**5. Growth & Career**
- "How are you growing in your role?"
- "What skills do you want to develop?"
- "What's your career trajectory looking like?"
- "What opportunities interest you?"
- "Are you getting stretch assignments?"

**6. Organization & Culture**
- "How's the engineering culture?"
- "What's working well?"
- "What would you change if you could?"
- "Do you feel heard and valued?"

**7. Concerns & Issues**
- "Any concerns you want to share?"
- "Anything keeping you up at night?"
- "Is there anything I should know about?"
- "Any suggestions for improvement?"

### Your Topics (10-15 mins)

**1. Context Sharing**
- Organizational updates that affect them
- Strategic direction and priorities
- Team changes or initiatives
- Recognition from leadership

**2. Feedback (If Appropriate)**
- Positive feedback: "I wanted to recognize [specific contribution]"
- Growth feedback: "I've noticed [strength/opportunity]"
- Career guidance: "Have you considered [opportunity]?"

**3. Career Development**
- "What's your ideal next role?"
- "What would help you get there?"
- "How can I support your growth?"
- "Let's create a development plan"

### Closing (3-5 mins)

**Summary:**
- "Let me recap what I heard..."
- "Action items: [list them]"
- "Anything else before we wrap?"

**Follow-Up:**
- "I'll follow up on [specific item]"
- "Let's schedule another conversation in [timeframe]"
- "Feel free to reach out anytime"

**End on Positive Note:**
- "Thanks for your honesty and openness"
- "I appreciate your contributions to [specific thing]"
- "I'm here to support you"

## Post-Meeting Actions

### Document Notes
- [ ] Key discussion topics
- [ ] Feedback about manager, team, culture
- [ ] Action items (yours and theirs)
- [ ] Concerns or issues to address
- [ ] Career development notes
- [ ] Positive feedback to share with manager

### Follow-Through
- [ ] Complete your action items promptly
- [ ] Share relevant feedback with their manager (respecting confidentiality)
- [ ] Address concerns or issues raised
- [ ] Support their career development
- [ ] Schedule follow-up if needed

### Manager Feedback Loop

**What to Share:**
- High-level themes (not specifics)
- Career development opportunities
- Positive feedback
- Organizational context

**What NOT to Share:**
- Direct criticism of manager
- Confidential concerns
- Personal issues
- Anything they asked to keep private

**Example:**
"I had a good skip-level with [Name]. They're doing great work on [project]. They're interested in [career area] - you might want to give them opportunities in that space. Overall they're happy and growing well."

## Skip-Level Best Practices

### Build Trust
- Be consistent (don't cancel frequently)
- Respect confidentiality
- Follow through on commitments
- Be authentic and human

### Listen More Than Talk
- Aim for 80% listening, 20% talking
- Ask open-ended questions
- Avoid interrupting
- Show you're paying attention

### Stay Neutral
- Don't triangulate (don't be messenger between IC and manager)
- Don't undermine manager's authority
- Support manager while hearing concerns
- Focus on solutions, not blame

### Be Action-Oriented
- Don't just listen - take action
- Address concerns promptly
- Follow up on commitments
- Show you value their feedback

### Respect Boundaries
- Don't micromanage through skip-levels
- Don't bypass manager except when necessary
- Support manager's decisions
- Escalate appropriately

## Common Scenarios

### Scenario: IC Complains About Manager
**Don't:**
- Take sides immediately
- Undermine manager
- Become messenger

**Do:**
- Listen fully
- Understand the issue
- Ask: "Have you talked to them directly?"
- Assess if it's a manager development issue
- Coach manager if needed
- Consider moving IC if relationship is irreparable

### Scenario: IC Shares Organizational Concern
**Do:**
- Acknowledge their concern
- Investigate if it's a real issue
- Share context if helpful
- Take action if needed
- Follow up on what you did

### Scenario: IC Wants Career Growth
**Do:**
- Understand their goals
- Assess readiness
- Create development plan
- Provide opportunities
- Support their growth
- Communicate with manager

### Scenario: IC Provides Valuable Feedback
**Do:**
- Thank them for feedback
- Share anonymized feedback with leadership
- Implement changes when appropriate
- Follow up to show impact
- Recognize their contribution

## Red Flags to Watch For

### Manager Issues
- Multiple ICs complaining about same manager
- Patterns of micromanagement
- Lack of feedback or development
- Trust issues

**Action**: Assess manager's capabilities, provide coaching, consider manager change

### Organizational Issues
- Common themes across skip-levels
- Culture problems
- Process friction
- Resource constraints

**Action**: Address systemic issues, share with leadership, create action plan

### Retention Risks
- IC mentioning other opportunities
- Low engagement
- Burnout signals
- Growth frustration

**Action**: Discuss concerns, create retention plan, address root causes

## Frequency Recommendations

### Monthly Skip-Levels
**For:**
- High-potential ICs
- New hires (first 6 months)
- ICs in critical roles
- ICs showing concerning signals

### Quarterly Skip-Levels
**For:**
- Stable high performers
- ICs in roles >6 months
- Standard check-ins

### As-Needed Skip-Levels
**For:**
- Specific concerns raised
- Before major decisions (promotions, moves)
- Manager changes
- Organizational changes

## Success Metrics

Track:
- Frequency of skip-levels conducted
- Themes identified across skip-levels
- Action items completed
- Retention rate of skip-level participants
- Manager feedback on skip-level value

## Notes
- Skip-levels are not a replacement for good manager-IC relationships
- They're a complement to catch issues early and build organizational trust
- Use them to develop future leaders and understand ground truth
- Always respect confidentiality and manager relationships
Conducting Effective Skip-Level 1-on-1s as a Director or VP

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