Save yourself the tuition fee - here are the red flags: 🚩 They don't code at all. When shit hit the fan at 1 AM, he was useless. Your CTO doesn't need to code daily, but they better know HOW when the team is drowning. 🚩 They put too much effort into looking "fashionable". The CTO who spent more time thinking about style than technical substance was gone in less than six months. He was building his personal brand, not our product. 🚩 They discuss "best practices" and jargon but never show battle scars. If they've never had a deployment disaster, they're theorists, not practitioners. Give me someone who's survived production hell over a conference speaker any day. 🚩 They want to rebuild everything from scratch. New CTO syndrome: "This codebase is garbage, we need to start over." The best CTOs I've worked with? They ship improvements while re-structuring the codebase for the long term. 🚩 They negotiate equity but never ask about business fundamentals. The CTOs who lasted? They grilled me about customer pipeline, churn, and how tech can truly add value. A true business-minded tech leader will build their own conviction on how tech can change the game. 🚩 They show disinterest and delegate speaking to customers to other teams. Our best CTO sat with angry users, apologised, and came back with features that actually mattered. 🚩 They build for perfection, not iteration. They presented 6-month or 12-month roadmaps for a "perfect" system. We need someone who ships weekly and fixes on the fly. 🚩 They've never worked at a company that failed. Success teaches ego. Failure teaches humility. After 4 CTOs, I'll take the one who's seen a startup die and knows exactly why. Most CTO hires fail because we hire for the resume, not the mission. Now that we're shipping AI agents at scale every day for the logistics/customs compliance space, we've learned: it's better to have a missionary who codes than a mercenary with a perfect LinkedIn. What expensive CTO lessons have you learned?