Leadership & Management

Director of Engineering

Your personalized pathway: 91 lessons tailored to your role.

Part 1: Wake-Up Call

What Happened in 2024-2025

Layoff Numbers Nobody Talks About

Which Roles Vanished First

What Comes Next (2026-2028)

Understanding Business Context

Navigating Ambiguity

Politics and Stakeholder Management

Creative Problem Framing

The Last Mile Problem

Domain-Specific Edge Cases

Part 2: New Playbook

The 10x Myth vs. Real Multiplier

Prompt Engineering: Not Just for Code

Reviewing AI Output: The Critical Skill

When to Use AI vs. When to Think

Building Your Personal AI Workflow

Claude and ChatGPT for Engineering

AI for Project Management

Eng ManagerTpmTech Lead

Product Thinking

System Design Judgment

Cross-Team Communication

Mentoring and Multiplying

Understanding the Business

Owning Outcomes, Not Tasks

Domain Expertise as a Moat

Part 3: Experience Gameplan

This Time Is Different

Your Experience Is Not Wasted

Your Experience Is Your Superpower

The Mid-Level Squeeze

From Coder to Multiplier

The AI Strategy Question

Lead the AI Transformation

Become the AI-Native Developer

The Advisory Path

From Coder to AI Director

Own System Design

Headcount Planning With AI

Board-Level AI Literacy

Stand Out in the Age of AI

Mentorship at Scale

Deepen Your Specialization

Multiply Your Team With AI

Build vs. Buy vs. AI

Talent Strategy in the AI Era

Build Your AI Portfolio

Stay Credible With Modern AI

Lead Projects With AI

The Staff/Principal Path

Manage the AI Transition

Thought Leadership That Matters

Learn Faster With AI

The Wisdom AI Can't Learn

Become the Go-To Person

Lead AI Adoption

Protect Your Team

The CTO as AI Champion

Pick the Right Specialization

Build Your Legacy

Negotiate Your Value

Mentor in the AI Era

Measure AI ROI

Mentor the Next Generation

Navigate Your First AI Layoff Scare

Navigate Ageism With AI

Build Your Technical Brand

Stay Technical at Senior Levels

Position for CTO

Your 30-Day Action Plan (Industry Sage)

Your 30-Day Action Plan (Junior)

Your 30-Day Action Plan (Living Library)

Your 30-Day Action Plan (Mid-Level)

Your 30-Day Action Plan (Senior)

Your 30-Day Action Plan (Strategic Leader)

Part 4: Your Role

Managing AI-Augmented Teams

Headcount Planning in the AI Era

Team Productivity Metrics in the AI Era

Agile in the AI Era

Project MgmtEng Manager

Hiring in 2026 — What to Look For

Part 6: Career Moves

What Companies Actually Hire For (2026)

Personal Branding for Your Role

Roles That Are Growing

LinkedIn and GitHub Presence in the AI Era

Roles That Are Shrinking

Conference Talks in 2026

Interview Prep With AI

Writing and Blogging as Career Insurance

Salary Negotiation in 2026

Networking in the AI Era

Remote vs Onsite in the AI Era

Building in Public

Freelancing With AI Superpowers

Creating Your Own Role