insights
AI and IT Outsourcing: Does It Change the Equation for Engineering and Support?
AI and IT outsourcing: does it change the equation for engineering and support?
•11 min read•
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Engineering Leadership
Explore all content tagged with "Engineering Leadership" across insights, frameworks, and resources.
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13 items
insights
Does AI Change Buy vs Build for Systems of Record? A CTO Decision Framework
In 2023, GitHub said developers using Copilot finished tasks up to 55 percent faster in a controlled study. That stat showed up in every board deck I saw for six months.
•12 min read•
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insights
Does the AI Revolution Change the Buy vs Build Decision? A CTO Assessment With a Decision Matrix
Does the AI revolution change the buy vs build decision?
•12 min read•
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frameworks
The Fig Tree (Strangler) Pattern: Replace Legacy Systems Without a Big-Bang Rewrite
Key Takeaways: The fig tree or strangler pattern works when you can control traffic at a choke point and measure outcomes per route.
•9 min read•
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insights
Clawdbot and the rise of scraping bots: what they expose, what they prove, and how CTOs should respond
Key Takeaways: Treat Clawdbot-style tools as a forced security review of your public web surface, not a one-off nuisance. The biggest risk isn't page views.
•9 min read•
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insights
Tech Stock Shakeouts: What CTOs Should Do When Markets Punish Software Multiples
Key Takeaways: Treat a tech-led selloff as a budget and risk reset, not a morale event. Reprice projects in weeks, not quarters.
•9 min read•
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insights
What a CIO Actually Does (and How a CTO Can Work With Them Without Losing a Quarter)
Most CTOs I talk to have a fuzzy mental model of the CIO. Not because they're careless—because the CIO job shape-shifts depending on the company.
•5 min read•
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insights
Certifications for Engineering Leaders: What Actually Matters for New Engineers, Aspiring CTOs, and Sitting CTOs
I've hired people with a wall of badges who couldn't ship. I've also hired people with zero certs who quietly carried entire systems through Black Friday.
•6 min read•
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insights
What a CTO Actually Does (and Why the Job Keeps Changing Under Your Feet)
Most CTOs I meet can describe their calendar, but not their job. That's not a knock-it's just what happens when the role is a moving target.
•6 min read•
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insights
The Enterprise AI Risk Map: What Breaks, How It Breaks, and What CTOs Can Do About It
Most CTOs I talk to aren't worried about whether AI "works." They're worried about what happens when it works just enough to get embedded into core workflows—support, underwriting, sales ops, security...
•8 min read•
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frameworks
Blameless Postmortems That Actually Change Behavior
Most CTOs don't have a postmortem problem. They have a behavior change problem. The doc gets written, the meeting happens, everyone agrees it was a great discussion, and then the same class of incident shows up again 6-10 weeks later.
•5 min read•
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frameworks
Run Incident Response Like a Bank: Discipline, Auditability, and Calm Under Fire
Most CTOs I talk to don’t struggle with detecting incidents—they struggle with the messy middle: unclear authority, too many cooks in the channel, executives asking for ETAs you can’t honestly give, a...
•6 min read•
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