one-on-ones

What this skill does

# One-on-Ones

> Design and run effective 1:1 meetings that build trust, develop people, and surface problems before they become crises.

## When to Use This Skill

- **New manager** setting up 1:1s for the first time
- **Resetting unproductive 1:1s** that became status updates
- **Onboarding a new direct report** with structured first conversations
- **Preparing for a difficult conversation** (performance, conflict, change)
- **Career development coaching** in 1:1 context
- **Scaling management** as team grows

## Methodology Foundation

| Aspect | Details |
|--------|---------|
| **Sources** | Andy Grove (*High Output Management*), Kim Scott (*Radical Candor*), Michael Lopp (*Managing Humans*) |
| **Core Principle** | The 1:1 is the direct report's meeting, not the manager's — their time to surface what matters to them |
| **Key Ratio** | Manager talks 10-30% of the time; listens 70-90% |

## What Claude Does vs What You Decide

| Claude Does | You Decide |
|-------------|------------|
| Designs 1:1 cadence and structure for your team size | Personal relationship-building approach |
| Generates conversation frameworks and question banks | Which questions fit each person |
| Creates agenda templates and running-notes docs | How to adapt for individual personalities |
| Prepares scripts for difficult conversations | Final wording and tone for sensitive topics |
| Suggests development discussion frameworks | Career advice based on your knowledge of the person |

## Instructions

### Step 1: Set Up the Mechanics

**Cadence by maturity:**

| Task-Relevant Maturity | Frequency | Duration |
|------------------------|-----------|----------|
| New or struggling | 2x/week | 30-45 min |
| Developing | Weekly | 30-45 min |
| Senior / independent | Bi-weekly | 45-60 min |

**Rules:** Same time each week. Rarely cancel. They own the agenda (shared doc, they add topics first). Private space for sensitive topics.

**30-minute structure:**

| Time | Activity |
|------|----------|
| 0-5 min | Check-in: "How are you, really?" |
| 5-20 min | Their agenda items |
| 20-25 min | Your topics (feedback, context) |
| 25-30 min | Commitments and close |

### Step 2: Master the Conversation

**Opening** — Understand where they're at: "What's on your mind this week?" / "How's your energy level?"

**Middle (their agenda)** — Coach, don't solve:
- "Tell me more about that."
- "What have you tried?"
- "What do you think you should do?"
- "How can I help?"

Resist the urge to fix immediately. Ask → Listen → Ask more → Let them reach conclusions.

**Middle (your topics)** — Keep secondary. Feedback, context, observations.

**Closing** — Capture commitments: "What are you committing to? What am I committing to?" Document and review next time.

### Step 3: Handle Different Conversation Types

**Career Development** (monthly/quarterly):
- "Where do you want to be in 2-3 years?"
- "What skills do you want to develop?"
- "What would make this the best job you've ever had?"

**Feedback:**
1. Context → 2. Specific observation → 3. Impact → 4. Their perspective → 5. What should change

**Performance concern:**
1. State the pattern with specific examples
2. Ask: "Help me understand — what's happening?"
3. Explain the impact
4. Agree on path forward with clear expectations and timeline
5. Document

**Validation checkpoint:** After a performance conversation, check in at the next 1:1. If no improvement after 2-3 follow-ups, escalate to formal process.

**Trust-building** (new relationship):
- "Tell me about your path to here."
- "How do you like to receive feedback?"
- "What do you need from me to do your best work?"

### Step 4: Troubleshoot Common Problems

| Problem | Likely Cause | Fix |
|---------|-------------|-----|
| "Everything is fine" every week | Lack of trust or wrong questions | Wait in silence longer; share your own challenges first; ask "What would you change if you could?" |
| Turns into status update | Habit, no agenda ownership | "I can read status — what do you need from me?"; use shared doc for status, meeting for discussion |
| Same complaints, no action | Venting without ownership | "We've discussed this for weeks. Are you ready to address it?" |
| Surface-level only | Trust not established yet | Walk-and-talks, share about yourself, be patient |
| Too busy to hold 1:1s | Too many reports or not delegating | 1:1s are core management work, not optional — restructure |

## Examples

### Example: Onboarding a New Report

**Week 1 (60 min):** Getting to know each other — their story, working preferences, how they like feedback, your context and priorities.

**Weeks 2-4 (30 min, 2x/week):** Frequent check-ins — "What's surprising? What's confusing? What do you need?"

**Week 4+:** Transition to weekly cadence with shared running doc. Add development topics monthly.

**90-day check-in:** "How's it going overall? What's working? What's not? What do you want to focus on next quarter?"

### Example: Resetting Stale 1:1s

**The reset conversation:** "I've noticed our 1:1s have become mostly status updates. I want to use this time for things you can't get elsewhere — challenges, development, feedback. What would make these more valuable for you?"

Then: implement shared agenda doc, change opening from "What's your update?" to "What's on your mind?", add 10 minutes for development each week, experiment with format (walks, coffee).

See [QUESTIONS.md](QUESTIONS.md) for a complete question bank organized by category (opening, work, development, relationship, closing).

## Skill Boundaries

### What This Skill Does Well
- Designing 1:1 systems and cadence for different team sizes
- Generating conversation frameworks and question banks
- Preparing scripts for difficult management conversations
- Diagnosing and fixing unproductive 1:1 patterns

### What This Skill Cannot Do
- Replace real human judgment about individual personalities
- Handle legally sensitive HR situations (consult HR/legal)
- Know your team members — you provide the context
- Substitute for building genuine relationships over time

## References

- Grove, Andy. *High Output Management* — 1:1 fundamentals
- Scott, Kim. *Radical Candor* — Caring personally + challenging directly
- Lopp, Michael. *Managing Humans* — Practical 1:1 advice
- Horowitz, Ben. *The Hard Thing About Hard Things* — Difficult conversations

## Related Skills

- [high-output-management](../high-output-management/) — Grove's full management system
- [radical-candor](../radical-candor/) — Feedback framework for 1:1s