running-effective-1-1s

Create a 1:1 operating system with templates for coaching and career conversations.

5|Updated Jan 19, 2026
One-click install
npx skills add https://github.com/oldwinter/skills --skill running-effective-1-1s
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: running-effective-1-1s
Source: https://github.com/oldwinter/skills/tree/main/lenny-skills/leadership-skills/running-effective-1-1s
Command: npx skills add https://github.com/oldwinter/skills --skill running-effective-1-1s

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) and references (resource) components.

What problem does it solve?

This Skill transforms your 1:1 meetings from status updates into powerful coaching and career development sessions, ensuring meaningful conversations and stronger team relationships.

Core Features & Use Cases

  • Design a 1:1 Operating System: Establish clear purpose, cadence, and meeting types for effective one-on-ones and skip-levels.
  • Coach, Don't Just Advise: Equip managers with tools to foster independent problem-solving through coaching questions and frameworks.
  • Drive Career Growth: Facilitate structured career conversations focusing on life stories, future dreams, and actionable development plans.
  • Use Case: A new manager can use this Skill to set up a robust 1:1 framework, including templates for shared documents, a coaching question bank, and a plan for career development conversations with their direct reports.

Quick Start

Use the running-effective-1-1s skill to create a 1:1 operating system pack for a new manager with 5 direct reports.

Frequently Asked Questions about running-effective-1-1s

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I stop 1:1 meetings from turning into status updates?

To stop 1:1 meetings from becoming status updates, establish a 1:1 operating system with clear purpose, cadence, and structured templates focused on coaching, career development, and wellbeing rather than project tracking.

What is a skip-level meeting and how should managers prepare for it?

A skip-level meeting connects managers with their direct reports' team members to build relationships and gather feedback. Prepare by using structured templates and workflows to facilitate effective skip-level conversations and address team concerns.

How to structure career development conversations with direct reports?

Structure career development conversations by guiding employees through their life stories, future dreams, and actionable development plans. Use structured career conversation templates to ensure meaningful and focused growth discussions.

What are the best coaching questions for managers to use in 1:1s?

The best coaching questions for 1:1s prompt independent problem-solving rather than giving direct advice. Use a coaching question bank and frameworks to equip managers to foster independent thinking and guide employees toward their own solutions.

Can I set up a 1:1 framework for a new manager with multiple direct reports?

Yes, new managers can set up a robust 1:1 framework for multiple direct reports. Create a 1:1 operating system pack that includes shared document templates, coaching question banks, and customized career development plans.

Why do my team members lack follow-through after our one-on-one meetings?

Lack of follow-through after one-on-one meetings often stems from unstructured conversations. Implementing a comprehensive 1:1 operating system with structured workflows and clear development plans addresses common issues like missing accountability and action items.