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The first blog designed to equip software engineers and aspiring leaders with the tools, tactics, and wisdom of a CTO who has successfully led engineering teams and navigated tech hiring challenges

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Dean Hiller

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The 3-Point Merge

Dec 17, 2025

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10 min read

The 3-Point Merge

Why Your IDE's Merge Tool Is Lying to You (And How to Fix It)

Dean Hiller
Dean Hiller
The AI Productivity Paradox: Why Some Developers Are Getting Slower While Thinking They're Faster

Sep 10, 2025

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6 min read

The AI Productivity Paradox: Why Some Developers Are Getting Slower While Thinking They're Faster

New Data Reveals a 40% Perception Gap Between AI's Promised Benefits and Actual Developer Performance

Dean Hiller
Dean Hiller
Why Skills-Based Hiring Outperforms Degree Requirements

Aug 26, 2025

•

7 min read

Why Skills-Based Hiring Outperforms Degree Requirements

What the Research Shows About Performance, Retention, and Hiring Without Degree Requirements

Dean Hiller
Dean Hiller

Archive

The 3-Point Merge

Dec 17, 2025

•

10 min read

The 3-Point Merge

Why Your IDE's Merge Tool Is Lying to You (And How to Fix It)

Dean Hiller
Dean Hiller
The AI Productivity Paradox: Why Some Developers Are Getting Slower While Thinking They're Faster

Sep 10, 2025

•

6 min read

The AI Productivity Paradox: Why Some Developers Are Getting Slower While Thinking They're Faster

New Data Reveals a 40% Perception Gap Between AI's Promised Benefits and Actual Developer Performance

Dean Hiller
Dean Hiller
Why Skills-Based Hiring Outperforms Degree Requirements

Aug 26, 2025

•

7 min read

Why Skills-Based Hiring Outperforms Degree Requirements

What the Research Shows About Performance, Retention, and Hiring Without Degree Requirements

Dean Hiller
Dean Hiller
Claude Code: 5X Your Development Productivity with AI Programming

Aug 13, 2025

•

6 min read

Claude Code: 5X Your Development Productivity with AI Programming

Best Practices and Techniques for Professional Developers in 2025

Dean Hiller
Dean Hiller
How to Hire Software Engineers Who Master AI Tools in 2025

Jul 29, 2025

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8 min read

How to Hire Software Engineers Who Master AI Tools in 2025

A practical guide to interviewing developers who can leverage ChatGPT, Claude, and other AI assistants to boost productivity without compromising code quality

Dean Hiller
Dean Hiller
CTO Leadership Through Experiments: Why Great Tech Leaders Don’t Make All the Decisions

Jul 16, 2025

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5 min read

CTO Leadership Through Experiments: Why Great Tech Leaders Don’t Make All the Decisions

How Fist-to-Five, One-Way Door Thinking, and Dictatorial Democracy Create Better CTOs

Dean Hiller
Dean Hiller
Hiring Fast Developers vs. Culture Fit: What Actually Works?

Jul 1, 2025

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7 min read

Hiring Fast Developers vs. Culture Fit: What Actually Works?

Discover what the data says about hiring for speed vs. fit—and how to make the right choice when building high-performing engineering teams.

Dean Hiller
Dean Hiller
The 20x Developer Is Real (And It’s Worse Than You Think)

Jun 17, 2025

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7 min read

The 20x Developer Is Real (And It’s Worse Than You Think)

What 500+ Interviews Taught Us About Developer Productivity

Dean Hiller
Dean Hiller
AI Is Multiplying Your Best Engineers—and Exposing the Rest

Jun 3, 2025

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4 min read

AI Is Multiplying Your Best Engineers—and Exposing the Rest

What every software manager needs to know about hiring and coaching in the age of ChatGPT

Dean Hiller
Dean Hiller
CTO Teachings

CTO Teachings

The first blog designed to equip software engineers and aspiring leaders with the tools, tactics, and wisdom of a CTO who has successfully led engineering teams and navigated tech hiring challenges

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