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1on1-prep

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Help leaders prepare effective 1:1 meetings with their direct reports. Use this skill when asked to: prepare a 1:1 agenda, generate discussion topics, create talking points for a specific person or situation, follow up on previous 1:1s, prepare for difficult 1:1 conversations, or structure career development discussions. The skill provides templates, question banks, and frameworks for different 1:1 types (regular check-ins, career conversations, performance concerns, etc.).

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leadership-skills

jkbennemann/leadership-skills

Plugin

leadership-essentials

Repository

jkbennemann/leadership-skills

skills/1on1-prep/SKILL.md

Last Verified

January 21, 2026

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Scope:
npx add-skill https://github.com/jkbennemann/leadership-skills/blob/main/skills/1on1-prep/SKILL.md -a claude-code --skill 1on1-prep

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Claude
.claude/skills/1on1-prep/
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Instructions

# 1:1 Preparation Skill

A framework for preparing and running effective 1:1 meetings that build trust, support growth, and surface issues early.

## Why 1:1s Matter

1:1s are the most important meeting a manager has. They are:
- **Their meeting, not yours** — The direct report sets the agenda
- **About them, not status** — Save project updates for standups
- **Relationship-building time** — Trust compounds over time
- **Early warning system** — Problems surface here first

## 1:1 Principles

### 1. Consistency Over Intensity
- Weekly or biweekly, same time, never cancel
- 30 minutes minimum, 45-60 ideal
- Rescheduling is okay; canceling erodes trust

### 2. They Own the Agenda
- Ask them to bring topics
- Your items come second
- If they have nothing, dig deeper (that's a signal)

### 3. Listen More Than Talk
- Aim for 70/30 ratio (them/you)
- Ask follow-up questions
- Silence is okay—let them think

### 4. Document and Follow Through
- Take notes (or have them take notes)
- Track action items
- Start next 1:1 with previous action items

---

## 1:1 Types & Templates

### Type 1: Regular Check-in (Weekly/Biweekly)

**Purpose:** Maintain connection, surface small issues before they grow

**Template:**
```
## 1:1 with [Name] — [Date]

### Their Topics (5-15 min)
- [Let them lead]

### How are you doing? (5 min)
- Energy level / workload
- Blockers or frustrations
- Anything I should know?

### Work Check-in (5-10 min)
- What's going well?
- What's challenging?
- Do you have what you need?

### Growth/Development (5 min)
- Any learning opportunities this week?
- Skills you want to develop?

### My Topics (5 min)
- [Your items — keep brief]

### Action Items
- [ ] ...
```

---

### Type 2: Career Conversation (Monthly/Quarterly)

**Purpose:** Discuss long-term growth, aspirations, development

**Template:**
```
## Career Conversation with [Name] — [Date]

### Reflection
- What's energized you most in the last quarter?
- What's drained you?
- What accomplishment are you

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