Sitemap - 2025 - Technocratic: CTO Insights from 20 years in the Trenches

How to Get the CTO Role

Behind the Curtain: How CFOs & CTOs Drive PE Success

The Economics of a Dev Team

Align or Lose: Your CEO’s Narrative Always Wins

How CTOs Can Scale Their Impact at PE-Backed Companies

MIT Says 95% of GenAI Pilots Are Failing at Companies - Here’s the Reason Why

ChatGPT-5 Release: Win or Catastrophe?

Ask Bobby: How To Better Leverage Your Team

$30M Business Case Template for CTOs

Practical AI Adoption in Software Engineering

How 1st Time CTOs Win in PE-Backed Companies

You Can Be Amazing at Board Meetings

Are Software Engineers Screwed? 4th of July Edition

No BS CTO Checklist for Product Launches

Lifting the Burden of Vendor Selection

How I Improved Our Project Estimates by 67% Without Changing the Team

Build vs. Buy vs. Partner

The Frankenstein Stack is Failing CTOs - Here's What Comes Next

Is AI Killing Product Management?

40 Ways to Assess Your Tech Team

Learning to Deliver (Every Time)

AI Governance in the Enterprise

The “Pick Me” CPO / CTO

Secret Way Elite CTOs Manage Their Teams

Building Innovative Product Teams

10 Ratios to Help Design Your Tech Team

Turn Yourself Into a 0 to 1 Leader

AI Isn’t Delivering For One Reason

The Pivot from Services to Product

What Story is Your Roadmap Telling?

10 Tips for Selling Ideas as a CTO

Rise of the CPTO (Chief Product & Technology Officer)

Tying Roadmap to Business Outcomes

What I Learned After 20 Years of Recruiting CTOs & VPEs

"OpenAI Will Lose" - AI Fireside Chat

AI Has a Big Problem In The Enterprise

Handling High Profile Tech Exits

The Reason Your Board Deck Isn’t Landing

Turnarounds Made Easy for CTOs

10 Big Mistakes to Avoid in an Acquisition

Product Strategy for Dummies

Why Do We Have So Many Developers?

Winning Strategies for CEOs & Top Execs

10 Unorthodox Mistakes Tech Execs Make When Starting a New Role

30-60-90 Day Plans Are Dead

Avoid Crashing in Your 1st Product Exec Role

The (Lost) Art of Roadmap Design

Managing Top Performing Tech Talent

Why Every Successful CTO Needs to Follow the Money

Product Strategy Rarely Matters

AI & The Impending Doom of Product Management

Don’t Screw Up Buying Enterprise AI Software

Why Startup Founders Fail and What Every Startup Needs to Know

AI Agents in the Enterprise: Hype or Substance?

We Go Deep on DeepSeek

10 Reasons You’re Not Ready For a Bolt-On

Death of the Offshore Engineering Industry

Building Winning Teams: Secrets from HP, Xerox & DEC in Their Heyday

7 Mistakes to Avoid in a Major Security Breach

Expectation vs. Reality for 1st Time CTOs

The Truth About AWS & AI

Tech Interviews in the Age of AI

Life of a High-End CTO

25 Tips for Building Effective Board Decks

How AI Will Change Software Engineering in 2025

The 7 Archetypes Every Engineering Team Evolves Into

The Right Way to Modernize Your Legacy Systems

Prioritizing in Chaotic Times

Overcoming the Innovation Barrier

Stop Tech-Splaining & Jump Up a Level

Start of Year Capacity Planning for CTOs

2025 Kickoff: Align Engineering to the Business