Management
Skews towards engineering management, but not exclusively.
See also Hiring.
Onboarding
Feedback
Influence
Leadership & Development
Elided Branches: How New Managers Fail Individual Contributors
Stop Overcomplicating It: The Simple Guidebook to Upping Your Management Game | First Round Review
12 Leadership Lessons to Learn From the Navy SEALs | Inc.com
Psychological safety: ‘You no longer have the option of leading through fear’
How to Scale Yourself Down — Not Up — as a Leader | First Round Review
4 Rules for Leading Dev Teams in Tough Economic Times - DZone
Five opinions I’ve kept, let go, and picked up as a software builder and leader
People First Leadership – Rebuffing the Negative Stigma – Simon Prior
How to Take Personal Development Off the Backburner — Tactical Frameworks for Leveling Up
The Signs of a Good CEO. Five Essential Features | by Roger Martin | Oct, 2024 | Medium
A Practical Guide to Executive Presence: Earning Respect | Stay SaaSy
Clear Thinking: Your Secret Weapon Against Leadership Stress – Scott Cochrane
Why doing less makes you a better leader - Blog - Tech Leaders Launchpad
Career Development: What It Really Means to be a Manager, Director, or VP - Kellblog
How to Hire a CEO. I often find boards of startups taking… | by Vinod Khosla | Jul, 2024 | Medium
All I Need to Know About Engineering Leadership I Learned From Leave No Trace - Jacob Kaplan-Moss
Team Management & Dynamics
How we structure our data teams at FreeAgent – Grinding Gears
This simple team activity builds psychological safety. | by Duncan Skelton | Medium
How to Build a High-Performing Team: Ten Vital Conversations
How Can You Foster Accountability On Your Team? | Management 3.0
What a Healthy Team Looks Like. The concept of “healthy teams” is… | by Hà Phan | Medium
Staying on the path to high performing teams. | Irrational Exuberance
Start Finishing, Stop Starting: Why I prefer Walk the Board Stand-Ups
Why your huge tech team isn’t delivering | by Roger Nesbitt | Noteworthy - The Journal Blog
Supporting Teams with Different Maturity Levels | by Sven Hans Knecht | Jun, 2023 | Medium
My critique of “the Spotify Model”: Part 1 | by Jason Yip | Jan, 2023 | Medium
Bricks of Love: create purpose and engagement with weekly updates
How you, the manager, can help your overloaded engineer dig out
Why Most Organizations Produce Brittle Teams Instead of Elastic Teams
Rethinking Agile 1/3: Teams, Trust and Leadership | by Andrew Winnicki | Mar, 2025 | Medium
Managers Make Teams Deliver More Value, Not Deliver More Output
Evolving annual reteaming at Redgate | by Chris Smith | Ingeniously Simple | Mar, 2025 | Medium
How to Use Delivery to Move from Blame to Trust - Johanna Rothman
Creative Peer Recognition: How to Get Better at Team Celebration
How organisations cripple engineering teams with good intentions
Goals, Strategy & Planning
How we score OKRs at FreeAgent. Objectives and Key Results (OKRs) have… | by FreeAgent | Medium
My take on why goal cascades are harmful and what to do instead | by Jason Yip | Oct, 2022 | Medium
The Transition: Layering sales onto a bottom-up self-serve product
We have a four-day work week, and you should, too | by Jonathan Mortensen | bit.io
How We Built Our Three-Year Strategy by Jonas Rieke | Inside Personio
Prioritization is a Political Problem as Much as an Analytical Problem
How Big Tech Runs Tech Projects and the Curious Absence of Scrum - The Pragmatic Engineer
3x in 3 years: Scaling an Engineering Organization | PagerDuty
Stop Letting OKRs Masquerade as Strategy | by Roger Martin | Nov, 2021 | Medium
Dual-Track Agile — the what, the why, the pros & the cons | Bornfight
Close Loops & Opening Minds: How to Take Control of Systems, Big & Small ARC337 - YouTube
Why backlogs are harmful, why they never shrink, and what to do instead
My preferred approaches to estimation on Agile projects | by Jason Yip | Jan, 2023 | Medium
🔥 Hot Take Alert #4: Annual planning is a colossal waste of time
TBM 41/51: Why Goal Cascades are Harmful (and What to Do Instead)
From Story Points to Slam Dunks — Planning for Success | by Matthew Croker | Agile Insider | Medium
What Sam Altman Just Taught Us About OKRs (Without Meaning To) – Eleganthack
JIT selection from independent streams: An alternative to the “big backlog” of work
The Anti-Goal Setting Guide: Creating Objectives People Actually Care About
TBM 403: The Seduction (And Folly) Of Rollups, Points, and (Most) Time Tracking
How to Reduce Planning, Deliver More, and Surprisingly, Reduce Pressure - Johanna Rothman
Performance & Metrics
Be good-argument-driven, not data-driven - Richard Marmorstein
5 Software Engineering KPIs to Consider for Your Next Board Meeting | CTO Craft
Goodhart’s Law Isn’t as Useful as You Might Think - Commoncog
Velocity defeats itself. Get acceleration instead – Jessitron
How to Measure Engineering ROI: A Practical Guide for SaaS CTOs
Beyond speed: Measuring engineering success by impact, not velocity - Stack Overflow
The Economics of Software Teams: Why Most Engineering Organizations Are Flying Blind - Viktor Cessan
Evaluating Managers: 5 heuristics to measure managerial impact
Am I a Good Manager ?. If you find yourself asking this… | by That Crazy Moment | Medium
Communication & Collaboration
Nonviolent communication and the concept of “denial of responsibility”
The subtle science of storytelling at work - Work Life by Atlassian
Communication Structures in a Growing Organization – Jessitron
Playing defense: How to control the narrative if your work is being questioned
How to Communicate When Trust Is Low (Without Digging Yourself Into A Deeper Hole) – charity.wtf
Delegation & Decision Making
Organization & Culture
Elided Branches: Structural Lessons in Engineering Management
How “Engineering-Driven” Leads to “Engineering-Supremacy” – charity.wtf
The Hierarchy Is Bullshit (And Bad For Business) – charity.wtf
Jade Rubick - How to build silos and decrease collaboration (on purpose)
Engineering Teams Are Just Networks | by Marianne Bellotti | Sep, 2021 | Medium
Lush CEO: ‘Happy to Lose’ $13M by Deleting Social Media Accounts
Death by Indigestion. More companies die of indigestion than… | by Bryce Roberts | Medium
Inside the all-hands meeting that led to a third of Basecamp employees quitting - The Verge
The US Federal Government Needs a VP of Engineering, not a CTO
All Basecamp policies are now on GitHub and licensed under creative commons
Approaches and Techniques to Break Down Silos: Learnings from QCon New York
Architects, Anti-Patterns, and Organizational Fuckery – charity.wtf
How to announce organizational change in your first 90 days | Lara Hogan
Can you run a company as a perfect free market? Inside Disco Corp
The Gervais Principle, Or The Office According to “The Office”
GitHub’s Engineering System Success Playbook - GitHub Resources
Design Your Organization for the Conflicts You Want to Hear About - Kellblog
Difficult Situations
Reviews & Meetings
Breaking Out of an Endless Cycle of Meetings | Mathias Meyer
Stand-up Meetings Are Dead (and What To Do Instead) - Honeycomb
Briefly: The Value of Meetings, and Some Alternatives | Kellan Elliott-McCrea
Towards better 1-on-1s: an awkward manifesto - Tyler Cipriani
The 1-on-1 Disclosure Framework. At work, people talk to me. Sometimes… | by Roy Rapoport | Medium
Specific Roles
What’s the Second Job of a Startup CEO? : YC Startup Library | Y Combinator
Welcome to the C-suite! How do CTOs succeed at the leaders’ table? | CTO Craft
How to build and scale a Staff+ engineering community | LeadDev
Engineering Levels at Honeycomb: Avoiding the Scope Trap - Honeycomb
Questionable Advice: Is there a path back from CTO to engineer? – charity.wtf
Your Board of Directors is Probably Going to Fire You | Reaction Wheel
Jade Rubick - Use these tips to improve your executive presence
Questionable Advice: The Trap of The Premature Senior – charity.wtf
Jade Rubick - Implementing software engineering levels (with fully-usable examples)
Raytha | The First 30 Days as a CTO or VP of Engineering for SaaS: What You Need to Know
Make an effective executive LinkedIn profile. | Irrational Exuberance
Getting a job as an engineering executive. | Irrational Exuberance
The Secret Value of Freelancers for Companies — Anselm Hannemann
Effective Positioning for Engineering Managers | by Mario Caropreso | Aug, 2025 | Medium
5 Things Founders, Investors and Recruiters Should Know about the CTO role
Knowing where your engineer salary comes from | sean goedecke
The farther you go up the ladder, the less it’s about your technical skills – Jim Grey
Why Should You (Or Anyone) Become An Engineering Manager? – charity.wtf
Books & Resources
Misc
Managing our costs through Covid-19 | by Hiroki Takeuchi | Medium
Why Don’t Tech Companies Pay Their Engineers to Stay? | by Matthew Dean | Marker
Manage Your Capacity, Not Your Time - The Engineering Manager
Make the change easy, then make the easy change - Software Product Development Pills
The 3M Rule of management - Software Product Development Pills
You should fear competition more than you fear your competitors - Software Product Development Pills
The product manager role is a mistake - Software Product Development Pills
How to Convince Management to Invest in the Tools You Need | liblab blog
What I say when people ask me for more money | by Brad Dunn | Medium
“Good engineering management” is a fad | Irrational Exuberance
A manager’s ultimate guide to effective succession planning - Work Life by Atlassian