Managing Up

This distills insights from 35 product leaders into practical managing up strategies. It pushes you toward proactive communication (weekly updates, bringing recommendations not just problems, starting exec conversations with strategy before details) and treats your manager as a resource to leverage rather than work around. The core advice is pragmatic: send "state of" emails, use structured formats like HPM (Highlight, People, Me), and understand priorities two levels up. What's useful here is the shift from abstract "communicate better" advice to concrete patterns like "say what you'll do, say you're doing it, say you did it" and knowing when to involve founders (high at strategy, high at quality, low in the middle). Most people under communicate upward then wonder why leadership feels out of touch.

skills.sh installs: 2K
GitHub stars: 1.5K
last updated: Aug 21, 2026

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Install

$ npx -y skills add refoundai/lenny-skills --skill managing-up --agent claude-code

Installs into .claude/skills of the current project.

Files

Managing Up for Leaders

Transform your relationship with leadership from a reporting line into a high-trust strategic partnership.

Help the user with managing up for leaders using insights from 21 guests and posts across Lenny's Podcast and Newsletter.

How to Help

Audit current communication - Identify if the user is currently reactive or proactive in their updates and how they handle disagreement.
Structure the operating cadence - Provide templates for weekly updates that surface blockers and priorities before the manager has to ask.
Script difficult conversations - Draft specific language for pushing back on ideas or asking for resources using business-centered framing.
Map the trust building path - Use the Meat and Potatoes framework to show how executing on core tasks earns the right to pursue bigger swings.

Core Principles

SKILL.md on GitHub

Details

Repository: github.com/refoundai/lenny-skills