From IT support to co-founding BorrowMyDoggy: Les Cochrne on his road to becoming a CTO

Welcome back to I'm a Software Engineer, What Next? The podcast for devs figuring out their next move. Hosted by James Wilson and Matt Sinclair, we talk honestly about what it takes to build a meaningful career in tech.This week we're joined by Les Chochrane, CTO at Practice Toolkit, building software for GPs inside the NHS. Les started in hardware, networks and second-line IT support, switched to interactive media at uni, did UX before anyone called it UX, taught himself the backend on a Rails app he built to replace the FTP site at a marketing agency, and then co-founded BorrowMyDoggy on the back of a weekend hackathon. After that: contracting, leading 24 engineers in sports data at IMG Arena (including being the employee rep when they had to let go of about 180 of them), and now CTO at a healthcare startup learning what compliance means for the first time.In this episode, we cover:-Validating his startup that he co-founded (BorrowMyDoggy) by sticking posters up on Hampstead Heath and having someone in Exeter sign up within 24 hours-What happens when 4,500 people sign up in an hour to a landing page that doesn't have a working search yet-Why "I need help" is the wrong way to ask for help, and what to say instead-Product engineer vs T-shaped vs Kent Beck's paint-drip people, and why time matters in the metaphor-Going from leading 24 engineers to being the employee rep during a 180-person redundancy-AI as a force multiplier "for good or evil" — and why introducing it into a six-month-release shop won't help-The LLM-generated PR quiz that makes you answer 10 questions about your own checked-in code before it merges-Centaur chess, supertanker captains, and Kahneman's type-3 thinking: cognitive offload and what we lose🗒️ Show NotesMike Jones (CTO, Love Holidays) — Les recommends his writing on engineeringPaul Ingalls (CTO, Uswitch)Kent Beck on paint-drip people"Seven Languages in Seven Weeks" by Bruce Tate (Pragmatic Programmers)James Stanier's newsletter and his "CTO daily driver" Claude skillThe "type 3 thinking" / cognitive offload paper Matt mentionsWhispr (voice tool James can't stop using)ThoughtWorks and the Forward Internet Group alumni network🗣️ GuestLes Cochrane — CTO, Practice ToolkitLinkedIn: https://www.linkedin.com/in/lescochrane/🎙 HostsMatt: https://matthewsinclair.comMatt: linkedin.com/in/matthewsinclair/James: https://www.linkedin.com/in/james-wilson-92170656🌐 More from us:https://whatnext.dev/https://quantumfaxmachine.com/